#186： The Legend and Reality of Frank Sinatra
Episode Stats
Summary
Frank Sinatra has been an icon of masculine coolness and swagger for decades. During his lifetime, he was able to create a myth and legend around himself that continues to exist today. But like all legends, when you look closer at them, you discover that the reality is much more complex than the story we like to tell ourselves about Frank Sinatra s life.
Transcript
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Brett McKay here and welcome to another edition of the art of manliness podcast old blue eyes
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the chairman of the board the voice Frank Sinatra has been an icon of masculine coolness and swagger
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for decades during his lifetime he was able to create a myth and legend around himself that
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continues to exist today but like all legends when you look closer at them that you discover
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that the reality is much more complex than the story we like to tell ourselves in the reality
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of Frank Sinatra's life very very complex today on the podcast I talked to James Kaplan is about
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his concluding volume of his definitive biography on Frank Sinatra it's entitled Sinatra the chairman
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and on the show James and I discuss how Frank Sinatra's career was in the tank after World War
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II and what he did to not only revitalize it but catapult himself into legendary status we also get
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into Frank's foibles his incessant drive for power and how that connected JFK and the mob together
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and we talk about Frank's enduring appeal as an icon of American masculinity a great show and when
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you're done be sure to check out the show notes for this podcast at aom.is slash Sinatra you'll find
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links to people and stories mentioned in this episode as well as a suggested Frank Sinatra playlist
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delighted to be here Brett thanks so much for having me
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so uh your second biography or biography of Frank Sinatra came out last year and this
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biography picks up it's called the chairman a subtitle and it picks up right after Frank Sinatra
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won the academy award for best supporting actor for from here to eternity um well you talk about in
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the book that before uh this this he won this award Sinatra's career was pretty much in the tank
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and I'm curious can you give us a little backstory like how did Frank Sinatra going from making thousands
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of bobby socks or you know sockers faint during the world war ii to you know people couldn't even
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recognize them on the streets in new york city yeah well the uh the book that just came out was the
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second volume of my biography of Sinatra second and final first volume was called Frank the voice
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and covered his rise uh to incredible superstardom mainly during world war ii world war ii was really what uh
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what jet propelled frank sinatra's career uh to its apex during those years because
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in those in that time he was singing these ballads of yearning that so rhymed with the way the country
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was feeling uh feelings of uh gentle sadness and and missing the boys who were away uh fighting overseas of
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course frank was not away fighting overseas he had been classified 4f a lot of people suspected that
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and called him a draft dodger but his records and and and william manchester who wrote a great history
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of uh the armed forces in in south pacific in world war ii where he also served very bravely as a marine
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uh said that sinatra was the most despised man in the armed forces uh because the all the all the guys
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fighting overseas felt that the sinatra the draft dodger was back at home uh fooling around with
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their women and in many cases they were right uh he wasn't a draft dodger he really did have a
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punctured ear drum but the perception lingered despite the perception though he sold a ton of records in
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world war ii after the war very very quickly things changed in america the political climate became very
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conservative uh and the popular culture in america of america really became extremely conservative
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after world war ii and tastes in popular music uh shifted gears just like that overnight suddenly
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people were no longer interested in uh in the ballads of yearning suddenly the big band era which had
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begun 10 years previously in about 1935 uh began fading away very quickly and america was in this odd
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state of jubilation and fear jubilation because the war was over and fear because the rise of the
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soviet union that accounts for the political conservatism and also i think the popular culture
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too so uh popular music music really uh got pretty terrible in the wake of world war ii very quickly
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there are a lot all kinds of novelty songs people wanted escape after world war ii so they were listening
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to stuff like how much is that doggie in the window uh they and sinatra who was still recording for
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columbia at that point uh but unlike many other uh unlike every other popular singer had enough power
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to dictate what he could record still he decided to go along with the tide he were he tried to to he did
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record a number of these uh crummy uh crummy uh crummy novelty numbers tennessee newsboy uh most infamously
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this the worst record he ever made mama will bark his his career after world war ii uh went down the
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tubes for a few reasons it wasn't just that tastes in popular music had changed uh it was really a
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multi-determined problem and a lot of the problems frank created for himself uh he was in 1947 early
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1947 he went to havana cuba to attend a mafia summit conference officially he went because he was there to
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entertain all these top uh mobsters uh it's also been alleged over the years that he brought a suitcase
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containing packed with cash for lucky luciano uh as tribute and he was cited in havana by a columnist
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for the hearst papers uh and this columnist began to write uh disparaging columns about sinatra's
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affection for the mob the hearst papers were very politically conservative again chiming with the times
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frank frank frank frank was a dyed in the wool a liberal democrat he was an fdr democrat the hearst papers
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hated him for that and suddenly they had something to call him out for well that wasn't enough for frank he
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also uh and from the day he set foot in hollywood he began stepping out on his uh on his young wife nancy
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uh with all kinds of holly hollywood uh starlets and uh in 1948 49 uh he stepped that up he was cited with
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lana lana turner uh and then he began this famous affair with ava gardner and uh in 19 1951 his uh
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his wife changed the locks on the house and divorced him but that wasn't all his record label columbia
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dropped him because he wasn't selling records his movie studio mgm dropped him uh for various reasons
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but they had gotten tired of him at that point his agents dropped him he wasn't selling records he
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wasn't really making movies he married ava in 1951 but his his career was sinking just as fast as her
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career was was rising and and uh as crazy as they were for each other frank and ava she began to get
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sick of his moping around and uh so his marriage wasn't even working well then it was it was a
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perfect storm of events and again frank himself had a lot to do with almost all of them so did he so he's
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at the bottom of his career lowest of the lows from what you've read and researched about him did he
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purposely like think okay i gotta do something about this i gotta do something to kickstart my career i mean
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did he deliberately start thinking about how he could catapult himself back into constantly
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constantly frank sinatra was the most important thing to frank sinatra throughout his entire
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his entire working life from the time he first uh started singing professionally in his uh in his
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very early 20s uh then went on the road with harry james and then tommy dorsey then went out on his
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own as a singer uh through his decline into his comeback and until the very end of his singing
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career the last concert he ever sang was in february 1995 after an incredible uh 60-year career
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every minute of every day frank sinatra was thinking about his singing and about his career
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that was his priority and so you can bet that during those years of decline he was obsessing
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every waking minute about how he could come back easier said than done though easier thought about
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than done he was incredibly frustrated incredibly depressed uh this is a period when uh he made uh
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he made a couple of the first of his uh his three suicide attempts he was as low as you could get and
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yes as you said before this is a point when he could walk through times square in new york
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where in 1944 he had created a mob scene around the paramount theater with those with those fabled
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bobby soxers uh he could walk unnoticed unrecognized sammy davis jr happened to be in times square
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and saw frank walking through with his collar up and nobody recognized him wow so okay you said
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that after world war ii the music uh tastes changed um during the 1950s but during the 50s is where a lot
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of the albums that we listen to today you know came out a lot of the songs that he he recorded so
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and it's kind of a weird time because like you said the big band era was over but yet rock and roll
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was just starting so what did frank sinatra tap into that into the like the american taste in music
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that people are like yeah this is great we like what he's doing how was it different from the big
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band stuff and uh but how was it also different from like rock and roll well sinatra did more than
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tap into uh sinatra really created a revolution in popular music rock and roll of course with its own
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revolution in uh in uh in in in popular music rocket 88 that uh that historic uh cut was recorded in 1951
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and rock and roll was on its way headed headed straight up elvis elvis would be walking down
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the street in just a couple of years after rocket 88 and meeting sam phillips uh uh historically in in uh
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at sun records in in uh in memphis but but sinatra created his own revolution in popular music it
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wasn't it wasn't so much a tapping into let's let's step back a couple of years and remember that between
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the end of world war ii and and around 1952 or 1953 people were just buying a lot of junk it was all
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this very transitory transient ephemeral music that just kind of feel good uh doggy in the window and
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and uh and mitch miller over at columbia had uh had sinatra uh recording these these crummy novelty
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numbers and he had uh other great artists like rosemary clooney was recording recording mambo italiano
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and come on to my house it was all very uh it was all kind of honky-tonk herky-jerky silly music
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sinatra was dropped by columbia records they they failed to renew his contract in 1951 and he drifted
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without a label for a couple of years in 1953 and the the importance of this cannot be overestimated
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an incredibly uh farsighted young executive at capital records out in hollywood uh a young guy
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named alan livingston decided to sign sinatra uh he signed sinatra because he knew that he knew how
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talented incredibly talented sinatra was and he had some ideas alan livingston did he signed sinatra to
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the standard artist beginning artist contract uh for for a sum in the three figures low three figures
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i mean we're talking a couple of hundred dollars and when alan livingston told his capital record
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sales force that he had just signed frank sinatra a room full of a couple hundred uh salesmen for
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capital records they all groaned this guy was such a drug on the market at that point but
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livingston's idea was he wanted to team this incredibly talented singer whose talent
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livingston recognized despite how down on his luck frank was he wanted to team sinatra with a young
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totally unknown uh arranger a guy named nelson riddle uh who i'm sure many of your listeners have
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heard of but then nobody knew who he was frank sinatra didn't know who he was and uh
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he teamed up sinatra with nelson riddle and uh they recorded a number uh very early in their
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collaboration together called uh i got the world on a string and when sinatra heard the playback of
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of that number that he just recorded with riddle's incredible arrangement because this guy could arrange
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like nobody else sinatra said i'm back baby i'm back he knew it he knew it and he knew he had
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it with nelson riddle and he and riddle began to turn out these singles and these albums
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that uh that created uh as i said a revolution in popular music and let me just say one more thing
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about that revolution because this is very important to understand we talked today about the great
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standards uh cole porter irving berlin the gershwins all these the great american songbook all these
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amazing numbers that stand the test of time so beautifully constructed that they that uh that
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that modern uh modern artists keep recording them over lady gaga buble you know and people will
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continue to record them for for decades and centuries to come because they are great and they're
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classics sinatra was the one who really created the idea of the standard these songs were
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not being recorded before sinatra insisted at the end of his columbia records career and at the
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beginning of his capital records career in 1953 sinatra insisted on recording them when he performed
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them in concert he would always credit the great songwriters so uh it's a long-winded answer brett to
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your question but what i do want to say that it wasn't something that it wasn't sinatra feeling the pulse of
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america sinatra was creating the pulse of america this was a great transformative artist who had uh who
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had ears who had a a musical understanding on a mozartian level and knew what he wanted to do with
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popular music and and uh created a revolution yeah that kind of leads to my next question uh because i
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thought it was interesting a lot what i love about your book james is that you you take us into these
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recording sessions and uh talk about the the dynamic between sinatra and the the arranger and the the
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uh or the orchestra and i think it's interesting i think maybe a lot of people today um think of
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sinatra as like pop stars of today that you know he had a nice voice and he just goes in and sings the
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songs that the music the musicians wrote and that's it but the way you describe the the recording sessions
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like sinatra was like almost a conductor uh almost and he was making these little improvisations
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and he could just tell right away that we need to like you know the violins need to do this
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so i mean was he different from some of the other popular crooners in the uh during the time because
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of his musical ability yes he was absolutely different uh he this was a musical genius uh this was a guy
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who knew exactly how he wanted those recordings to sound we talk about record producers uh the great
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george martin just died a couple of uh days ago and a great great producer and uh producers today uh
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people like niall rogers and pharrell williams these are people who go into a studio and shape every
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every every bar of every song every second of every every track that that uh that's recorded
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sinatra had people who were called producers but sinatra really produced all his own albums and all
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his own singles he was the guy who knew exactly how he wanted these records to sound he was the guy who
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had such incredible ears that if the third violin in his orchestra and sinatra by the way was a guy who
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revered musicians he he never wanted to be in an isolation booth singing uh when he was recording
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he always wanted to be out there with the musicians if the third violinist was a half note off he would
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look he would stop the music and freeze the guy with uh with a glare from those electric blue eyes and
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say where you working next week sinatra knew exactly how he wanted these uh these songs to sound and
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despite the fact that this is a guy who who really couldn't read music he he he he couldn't read he
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still knew his way around a score and so he could say uh bar 45 uh shouldn't that be maybe an f natural
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instead of an f sharp he knew stuff like that and we also have to remember that these songs he was
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recording unlike the songs of today all came from written arrangements these were uh these were charts
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these were very detailed uh arrangements that were written by great arrangers such as riddle and billy may
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and uh and uh uh sinatra worked with dozens of terrific arrangers up to quincy jones and klaus ogerman and
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don costa and uh gordon jenkins these were all brilliant men uh with whom sinatra
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purposely allied allied himself he he hired these guys because he knew what they could do for him but
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sinatra was the boss right so i mean i love sinatra's music i mean i listen to uh serious sinatra on
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a serious f you know xm radio all the time um but the thing that i've always been conflicted about the
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guy because he's like an extremely complex character uh super talented i love his music but then
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you do such a great job in the book painting this the complexities of sinatra i mean like the man had
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a lot of paradoxes about him and as you said earlier some of these uh sort of the the darker side of
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sinatra uh caused him problems with not only his family life his love life but also his career so can
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you talk about some of these personality paradoxes and and how that affected friendships uh business
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associates and even uh his his lovers and his wife and ex-wives yeah uh yeah this was well there there
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are a few things you have to talk about when you're talking about sinatra's personality he was as you say
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this was a musical genius uh but he was also a guy who could uh who also uh also had a genius for
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making himself dislikable and i spent 10 years writing these two books about sinatra and there were a lot
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of times when i disliked him when i was writing about him but i never got bored with him uh he wasn't he
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was never boring uh there are a few things you need to talk about when you talk about the demons that
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were inside sinatra one one big one was his mother uh his mother was named dolly sinatra she was a
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volcano she was under five feet tall little tiny woman who was brilliant uh swore like a sailor
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uh uh she was a democratic party organizer in uh in hoboken new jersey where frank grew up she spoke
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every dialect of italian when she went around hoboken getting out the vote for franklin delano roosevelt
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uh she was she was volcanically she had a volcanic temper she has she was uh pathologically impatient
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and sinatra in many ways was the same person as his mother but this was a mother who
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sinatra later said he never knew whether she was going to hug him or hit him and that was literally
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true she he was never certain of his mother's uh love for him and that really conditioned his
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relationships for the rest of his life especially with women his daughter younger daughter tina sinatra
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wrote a wonderful memoir and and wrote in her book my father was a deeply feeling man who was unable to
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attain an intimate relationship with another human being and that included all the many hundreds
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if not thousands of love affairs he had he he he loved women in a lot of ways but he never really
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loved it was very very difficult if not impossible for him to be intimate with somebody else okay so then
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you have to add all that all that that i just said to the fact that this was a kid who uh who was a
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musical genius he said in later life that when he was walking around as a kid he heard the music of
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the spheres well that sounds very high-flown and exaggerated but i think it was literally true this
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is a guy who heard sounds in his head that other people didn't hear and so there he is walking around
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hoboken new jersey in the 1920s in the 1930s a very tough town where if an italian kid walked across
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the the wrong street into the irish neighborhood he'd get the crap beaten out of them uh and uh this
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was a kid who was a genius that was not easy to walk around with uh so he kind of had to keep that
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hidden all his he was a highly highly strung guy very oversensitive he had to keep that hidden he he
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wanted to he he always wanted to seem tough that was that was important in hoboken when he was a kid
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it was important when he had grown up and the toughest guys of all when he was growing up in
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hoboken the 20s and 30s as an italian american kid when italian americans uh one of the things i
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learned writing writing these books uh it's it's easy sometimes to sort of feel this reflexive
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nostalgia for the way america used to be oh things were better in the old days when men were men and
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women were women and you know some of that's true uh there was a lot that was very bad in this
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country in the old days and the the very worst thing that i found was this very easy reflexive
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uh racism that existed in this country uh there's still a lot of it around but there was it wasn't
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even questioned in those days if you were a white anglo-saxon protestant male uh you could and you had
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some money you could uh you could be in the ruling class if you didn't you were out of luck and italian
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americans were just a half a step above uh african americans on the social scale and italian americans
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like african americans were looked on as happy singing dancing people uh and and and also uh who now
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and then uh murdered people right they were they were either clowns or they were mobsters and that was
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that was rough for frank to live with but he as soon as he began performing in clubs he began running
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into these guys who ran the nightclubs in those days and they were the mafia the mafia ran the nightclubs
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and and a lot of them were italian america italian american the mobsters uh and and frank uh idolized
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these guys they were men of power they were men of strength and he saw them incorrectly but he felt
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they were men of honor too so uh so this is a guy who is full of demons and this is a guy who's highly
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strung and oversensitive and a musical genius and whose mother didn't really love him and boo-hoo that
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sounds sad but if it happens to you it's real and it happened to him he couldn't really form an intimate
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relationship he was too highly strung and once ava threw him over ava gardner threw him over in the
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early 50s he began to drink pretty seriously alcohol became a big part of his life and he was a mean
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drunk he was an angry drunk and he had all these demons inside and when he drank the demons would come
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out so there is a there's an answer to your question there are an awful lot of things inside sinatra that
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were bugging him and uh and they could make him behave very badly right i mean going back to uh the
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volatility i mean you had these you describe encounters where you know he would go after men
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who were like twice his size there was an encounter where he went after uh john wayne
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yeah the parking lot unbelievable frank sinatra was five foot seven five foot seven in the stocking feet
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and until he put on some weight uh in his 50s he was a guy who weighed maybe in the 120s 130s he's a
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little man with thin wrists and and delicate hands but he had this volcanic temper same as his mother did
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he was pretty fearless and when he was in his cups when he had a couple of drinks in him and he was
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feeling angry about something yeah i mean he went right up against john wayne uh and you're talking
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about a guy who was six foot four and who was a genuine tough guy uh frank frank wasn't afraid uh for a
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second standing in front of john wayne and john john wayne uh didn't want to fight frank sinatra it
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wasn't that he was scared he just didn't want to fight him uh to his credit right yeah and i thought
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it was funny i mean the circumstances of the fight was there's a dose of irony to it because it was like
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a party and then vegas and benefit and sinatra was dressed like a indian squaw yes he was it's in the
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old politically incorrect terminology yes yeah i'm not allowed to say that anymore right exactly that
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that's how he was dressed that's how that's how you say indian woman uh native american woman and
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and there's wayne the duke with his uh he's six foot four in his stocking feet and he's got on the
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cowboy hat which makes him about six foot nine right and there they are facing off in a parking lot yeah
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so yeah this these this this personality of sinatra so he had the mother the issues with his mother and
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this volatile and it seems like yeah he had a chip on his shoulder uh being an italian american and he
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was talented and he knew it um and so it kind of the theme that you actually that you you see throughout
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the book and i think all these these three things come together with is that sinatra was very interested
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in power uh not only in business but it also carried over he wanted to get into the political
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arena we'll talk a little bit more on his relationship with uh jfk but what did he do i
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mean why was he obsessed so obsessed with power and what did he i mean did he have like some common
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tactics or power pulleys that he would use on people to get what he wanted well power was always
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important to him from the beginning again this is a guy who as a kid had felt himself to be weak had
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felt himself to be one down as a small person as an italian american as a as a guy who knew he had
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the goods to become the best popular singer of all time uh but at first nobody knew it but him
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uh this is a guy who had to uh learn to throw his weight around power was very important to him
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commercial power the power of his career uh when he first uh when he first broke through after he
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went out on his own as a popular singer and became a superstar and then went out to hollywood and and
00:29:11.980
signed with uh signed with mgm and and and and quickly became one of the hottest stars around uh hollywood
00:29:20.780
uh in in the 40s um he knew he had power and uh that power meant an enormous amount
00:29:28.660
to him when his career declined after world war ii for that uh that terrible period between about
00:29:38.240
1946 and uh and 1953 when when he signed with capital records and began uh shooting from here to
00:29:46.400
eternity uh the movie that would win him the oscar and that oscar would begin his comeback during that
00:29:53.400
terrible period that that seven years of bad luck when he said it felt like all every day was monday uh
00:30:01.080
he knew he felt acutely what it was like not to have power to lose power to be powerless to have had it
00:30:09.200
i mean it's one thing uh to have never had power and to and to yearn for it but imagine having the kind
00:30:17.460
power he had been completely losing it being uh looked on by everybody as as a loser failure has
00:30:24.260
been uh so it was very important for him to get it back when he began to get it back when he when he
00:30:31.620
began making those sublime albums with nelson riddle when he began shooting that great movie from here to
00:30:37.700
eternity and then suddenly suddenly he went from zero to 60 and suddenly the offers were all pouring in
00:30:45.120
again and uh movie offers singing offers tv offers everything very very quickly uh as the offers
00:30:53.320
poured in the money came in and the power began to increase and uh he he held on to everything he
00:31:01.480
could grasp and uh he relished the acquisition of power the paradox of it brett is that uh the more
00:31:10.080
power he got uh and it's it's really kind of like the legend of midas who the kid the fabled king
00:31:16.460
everything he touched turned to gold but then he had nothing to eat he had nobody to love because it
00:31:22.140
was all just gold sinatra was very much like that he acquired all this enormous power financial power
00:31:29.360
power in popular music power as a as as one of the top movie stars around uh and and yet he he couldn't
00:31:38.840
really get close to anybody else it was a source of of terrible sadness to him and it was a it was a
00:31:46.840
sadness that he tried to drink away that he tried to party away that he tried to uh
00:31:51.860
and that he tried to sing away uh but it was it was a sadness that he really couldn't banish the power
00:32:00.880
was enormous and it was very important to him and he uh and as i said he loved it but he he couldn't
00:32:10.000
figure out how to hold on to the power and uh and be and be truly happy at the same time and was that
00:32:16.780
desire for power is that one of the things that drew him to the the mob yes it was one of it was one
00:32:24.820
certainly one of the things that drew him to the mob he saw these guys as powerful guys and uh he saw
00:32:30.720
them really as uh as america's kind of uh kind of a uh a a shadow power in america you had the
00:32:40.240
government you had the corporations and the mob had an awful lot to do with running america in the
00:32:45.980
1920s 30s 40s 50s and 60s they're still around today but in a more complicated way and they're
00:32:54.320
more different kinds of mobs but back then it was the italian mob and to a less somewhat lesser
00:32:59.220
extent the jewish mob and they ran the nightclubs they ran the record business they ran a lot of
00:33:04.120
businesses and sinatra uh as i said before idolized them um and uh and loved to hang out with them and
00:33:12.000
in some corner of his soul kind of would have loved to have been one of them uh he wasn't he was who he was
00:33:21.020
it was the same uh attraction to power that that uh that drew him to jack kennedy the first time he
00:33:30.140
ran into him in in 1955 and okay so we we the the power was what drew sinatra to kennedy but the
00:33:39.000
feelings were sort of not completely mutual we'll talk about how sinatra was really obsessed with
00:33:43.480
kennedy and kennedy was a little more aloof but what did kennedy why was kennedy attracted to frank
00:33:49.420
sinatra well um i i i how are we rated here i'll try i'll try to be uh i'll try to be i'll try to
00:34:00.840
stay pg uh jack kennedy from uh from an early age jack kennedy was uh was a brilliantly gifted man in his
00:34:11.340
own right but he was also he was a prince his father joe kennedy had uh had become a uh a mogul
00:34:19.960
in hollywood in the 1920s brought into rko studios and as a young prince even before he went off to
00:34:25.860
world war ii jack kennedy began going out to hollywood and what he loved about hollywood was
00:34:32.060
women hollywood hollywood was the uh was the center of the universe the world capital of freakishly
00:34:40.320
beautiful women and john kennedy from an early age wanted to score with every last one of them much
00:34:46.180
as frank sinatra did well when they met in the mid 50s uh jack kennedy was a politician on his way up
00:34:54.200
he was also married he had been married for a couple of years to jacqueline bouvier and uh uh he was
00:35:01.180
delighted to be married and in many ways took delight in his wife but he uh had a complete uh kennedy had a
00:35:07.940
complete double standard uh and and uh and still saw fit to try to bed every beautiful woman he can't
00:35:16.340
he saw sinatra as uh as a magnet for beautiful women and beautiful women were always around sinatra
00:35:24.320
because sinatra had this power in hollywood and power in popular music in the nightclubs and and in
00:35:29.440
las vegas and uh kennedy found it intensely glamorous and intensely uh intensely attractive
00:35:39.640
and uh and uh and and so this was his pull to sinatra sinatra had his own uh rather different
00:35:47.680
reasons for being pulled toward jack kennedy yeah and it was the way you describe it uh yeah like you
00:35:54.240
like i was reading the book there's moments in the book where i was like man this is this is gross
00:35:57.860
um it's kind of repulsive uh i thought it was interesting as we in america today we kind of
00:36:02.780
venerate kennedy sort of this you know the whole camelot thing but i thought it was interesting that
00:36:07.980
whenever kennedy came out to hollywood he'd want to talk about he'd always shift the direction to
00:36:12.700
hollywood gossip like yes he read the the gossip rags and who was sleeping he wanted to know who's
00:36:17.800
sleeping with who and yeah that was really interesting yeah well it's very hard to find any any uh
00:36:24.640
really any figure of of great stature who is an unmixed blessing you read about lyndon johnson you
00:36:33.400
read about franklin roosevelt uh these uh even dwight eisenhower uh right uh dwight eisenhower the king
00:36:40.980
of the boring 50s uh you know he had a he famously had a mistress during world war ii kay summersby
00:36:48.040
he he it's very hard to find figures of great power who uh who are just purely good and jack kennedy
00:36:56.640
was a complicated guy there is something i think to venerate uh about jack kennedy although his legacy
00:37:03.380
was very tragically incomplete this is a guy who was a great leader and who was brilliantly articulate
00:37:10.060
and witty and uh uh in in in many ways was uh was uh could have been a wonderful president uh but he
00:37:20.620
was also a deeply flawed man and sex had a great deal to do with it right and it was the um that's
00:37:28.480
kind of where the the mob like the women in the connection of women and sinatra and kennedy and that
00:37:35.740
kind of where that's where the intersection of the mob came in that's where kennedy kind of got in
00:37:39.680
trouble a little bit uh because there's one woman in particular that was also seeing one of the top
00:37:44.480
ranking mobsters at the time and i guess j edgar hoover was really after the kennedys and had all
00:37:49.260
this evidence and that was that the i guess that was the cause of the split between sinatra and kennedy
00:37:55.260
correct yeah although this the split really the the the fisher began earlier than that he even began in
00:38:02.640
the campaign year of 1960 when kennedy was campaigning against nixon for the presidency
00:38:07.920
kennedy's family had a lot of misgivings about uh frank sinatra and about their candidate and their
00:38:14.200
their golden knight jfk associating with frank sinatra kennedy family didn't like frank sinatra's
00:38:21.560
associations they didn't they they knew about uh his criminal associations but even uh even more
00:38:28.400
pressingly for the kennedy family frank sinatra was a guy who was uh he wasn't he wasn't high class he
00:38:36.780
was he he hung around he was he was the king of vegas he wasn't a guy that they wanted their candidate
00:38:42.600
associated with but uh but jack kennedy kept associating with him uh he he he clung to sinatra uh because he
00:38:52.240
had uh jfk really had this kind of precocious uh understanding of how important show business
00:39:00.360
could be uh in politics of how uh how show business figures could help political figures uh gain the
00:39:09.320
power that they wanted it was very uh smart of him but his family his family rebelled against it and then
00:39:16.840
uh once he once he got into office uh a couple of things happened that uh that that were very uh very
00:39:26.000
bad and very troubling and yes they centered around one young woman named judy campbell a girlfriend of
00:39:33.820
sinatra's whom he introduced to uh to jack kennedy in las vegas in 1960 and then very soon afterwards
00:39:42.120
uh introduced to his friend the chicago mobster the head of the chicago mob sam john canna and in
00:39:50.400
short order jack kennedy was in office as uh as the head uh the leader of the free world the president
00:39:57.420
of the united states and sleeping uh with a woman who was also sleeping with the head of the chicago mob
00:40:04.720
and uh j edgar hoover the head of the fbi found out uh about this and told the attorney general
00:40:12.120
robert kennedy jack's brother about it and uh jack kennedy who had been on his way out to uh for some
00:40:19.680
fun and son at frank's place frank sinatra's place in in uh uh in palm springs uh very quickly changed his
00:40:30.540
plans when his brother the attorney general told him you can't you may not stay at frank sinatra's
00:40:36.580
house you have to you have to cut the cord no more hanging out with this guy yeah um and how did
00:40:43.200
that affect sinatra's political life afterwards was he still um heavily well he became he it was it was
00:40:51.120
a horrible humiliation for him that that uh the president who had been going to stay at his palm
00:40:57.060
springs house stayed instead at bing crosby's house in palm springs uh humiliation was always a
00:41:04.720
hair trigger was always a point of volatility for sinatra it really it really set him off any hint
00:41:11.740
of being humiliated this was a huge public humiliation and sinatra uh never oddly enough never blamed
00:41:20.240
jack kennedy for it he blamed bobby kennedy for it uh but that was really the beginning of the
00:41:27.040
end of his relationship with the kennedys and it was the very beginning of the end of uh of frank
00:41:34.760
sinatra's life as a liberal democrat he stayed a democrat uh through most of the 60s but by 1968
00:41:44.940
uh when jack kennedy was gone uh and he uh sinatra began to began to campaign for hubert humphrey who was
00:41:56.560
running against nixon that year but uh humphrey's people very quickly found out about frank's
00:42:02.960
unfortunate friendships with uh with certain with certain parties in organized crime and humphrey
00:42:09.320
dropped him uh much as jack kennedy had dropped him and and 1970 ronald reagan was running for
00:42:17.160
governor of california and to the horror of frank sinatra's democratic uh friends his liberal pals
00:42:24.600
sinatra supported ronald reagan and that was the beginning of uh frank sinatra republican instead
00:42:33.760
of democrat interesting um so we can't talk about uh this part of frank sinatra's life without talking
00:42:40.300
about the rat pack because i think if you lived in if you're a man if you're a boy in college you
00:42:45.680
probably had that famous sans poster of the rat pack in front of the the famous sans sign yeah um it's
00:42:52.320
become a it's it's a legend but i thought it was you kind of talk about the create you talk about
00:42:56.280
the creation of the rat pack that it was almost accidental um can you tell us a little bit about
00:43:00.660
how that formed and like uh what went on in the shows and why did people respond resonate so much
00:43:07.080
with these uh these impromptu shows that happened in the sans hotel it was impromptu uh and it was kind
00:43:13.920
of accidental uh sinatra dean martin sammy davis jr peter lawford joey bishop were shooting movie
00:43:19.900
called oceans 11 uh which became the seminal primary rat pack movie they were shooting that
00:43:27.500
movie in vegas in early 1960 that was also a time when jack kennedy loved to he stopped through vegas
00:43:34.540
a couple of times during that period january february of 1960 because it was just so much fun all the
00:43:41.640
guys i mentioned well the three primary guys frank and dean and sammy were all booked to open at the
00:43:49.720
sans uh hotel casino in las vegas sequentially in in that month of january 1960 but what happened
00:43:58.300
instead because they were having uh such a blast uh shooting this movie that really was not a very
00:44:06.480
good movie in fact it's kind of a terrible movie but but but hugely influential and and it's uh kind
00:44:13.720
of like a car wreck that movie it's you can't quite take your eyes off of it it's so influential not a good
00:44:19.420
movie but they were and probably not a good movie because of all the fun they were having shooting
00:44:24.360
it sinatra was the first one booked at the sands in january 60 and one night dean martin started
00:44:30.960
heckling him uh from off stage frank who took his act very seriously his singing very seriously dean
00:44:38.000
martin always thought too seriously uh first was kind of kind of taken aback but then he laughed
00:44:42.720
and from that laugh uh dean martin jumped up on stage and and the rat pack was born soon they soon
00:44:51.300
they were all interrupting each other's acts and soon they were all performing together on stage
00:44:55.780
and this was at a point vegas 1960 it's very hard to imagine you have to imagine your way back into a
00:45:02.740
different time a different place a different state of mind this was a time when uh when this was a time
00:45:10.920
when a woman couldn't have a credit card when women were meant to be wives and mothers and nothing
00:45:17.640
else and this was a time when uh smoking and drinking and saying naughty words on stage was seen as
00:45:26.400
as very fun and and vegas was the capital of naughtiness and these guys created in their breaking
00:45:36.120
each other's acts up and going on stage and making all these uh making all these drunk jokes and these
00:45:42.320
racial jokes about sammy davis jr they were the naughtiest thing going and uh the crowds in vegas
00:45:49.880
loved it and the rat pack became a legend you look at it today people feel different ways about it i happen
00:45:57.960
to think uh i happen to think from my perspective many years later that it was that that almost everything
00:46:05.100
they did on stage uh doesn't hold up very well unlike sinatra's singing uh it doesn't hold up it's
00:46:12.780
just not you had to be there you had to be there at that time when everything naughty was fun well
00:46:17.900
everything naughty that was naughty then it's it's not naughty anymore and so the the humor isn't funny
00:46:24.560
the racial humor is uh it's kind of offensive and uh and yet and yet the image of these guys in their
00:46:33.200
tuxedos with the ties loosened on stage looking so handsome and act acting so silly and uh in such
00:46:42.120
a stylish way uh people uh men and women are very willing to overlook the silliness uh the offensiveness
00:46:52.000
of the a lot of the material overlook that and really just look at the style and instead and so
00:46:58.040
this is why the myth of the rat pack endures yeah yeah then when you talked about some of the
00:47:02.800
the jokes at sammy davis jr's expense man i felt that kind of punch in the gut i felt bad for the
00:47:07.920
guy yeah it it it uh you know it it it's very i one of the very many people i interviewed for the
00:47:16.240
second volume of my sinatra biography was the great quincy jones the african-american
00:47:21.480
musician and arranger a brilliant brilliant man and he was uh he arranged a great count basie album
00:47:31.600
count basie sinatra album and he he conducted and arranged uh sinatra's uh famous shows at the sands
00:47:39.400
a few years after the rat pack shows in 1965 1966 and sinatra used to stand up on the stage in the
00:47:48.240
showroom of the sands uh the copa room and he would make these silly uh uh racial jokes i asked
00:47:55.180
quincy jones what did you think when you're there on the podium conducting the the great count basie
00:48:00.460
band and there's sinatra making these uh amos and andy jokes what do you think and and quincy jones
00:48:06.380
said i didn't like it very much and why should he have and and they don't sound very good today
00:48:11.980
you know i don't like him very much either but back then back then it was a different time and a
00:48:19.400
different place and i'm not saying those jokes were right but the audiences then thought they were
00:48:25.320
just hilarious and of course they were white audiences right um then there's the other kind of
00:48:30.400
the other paradox about sinatra though is even though he'd make these you know politically incorrect
00:48:34.100
jokes at the expense of sammy davis jr he was a really good friend to him to understand there's
00:48:38.840
some they had some falling outs but uh you know he kind of stuck out his neck a few like that one
00:48:43.000
time that he stood as a best man at sammy davis's wedding to the white model sinatra was was really
00:48:50.020
he when when sinatra was in his late teens uh and just beginning to sing and before anybody had a clue
00:48:58.320
who frank sinatra was he used to he used to go to west 52nd street in manhattan this was a block
00:49:04.820
between fifth avenue and sixth avenue in manhattan today it's all glass office towers back in those
00:49:11.240
days it was all brownstones three three story buildings and in the basement of every building
00:49:16.160
was a jazz club you could walk down this block and there were 50 jazz clubs and in the basement of
00:49:21.660
every one of these buildings there was a great jazz club and these geniuses you could you could see
00:49:27.360
count basie you could see duke ellington you could listen to billy holiday ella fitzgerald
00:49:32.920
and sinatra stopped in every one of those jazz clubs and he idolized these he he knew great
00:49:39.640
musicians great musicianship when he heard it he knew these these african-american artists
00:49:45.120
were geniuses and they carried themselves like royalty and that's how sinatra regarded them and he
00:49:51.440
as a liberal democrat from the beginning of his life uh and even though he switched to a more
00:50:00.320
conservative political stance sinatra was always a passionate advocate of tolerance and he walked
00:50:07.280
the walk as much as he talked the talk and even though he could he had this disagreeable side to
00:50:13.340
him he had this paradox that he could make the silly racial jokes uh he uh he stood behind he stood
00:50:21.880
behind his feelings yeah so this is the art of manliness podcast i gotta ask this um why is
00:50:28.540
sinatra still such a potent icon of american masculinity even today um and what was it what
00:50:36.040
was it about him that you know like there's that famous quote women wanted him and men wanted to be
00:50:40.740
him yeah what's going on there well i think you have to look deep underneath uh everything uh yes we
00:50:49.880
can look at the we can look at the aura the mystique the style of the rat pack i think i think that will
00:50:57.040
go on for a long time uh young people love that young people love to think about it drink the martini
00:51:04.280
smoke the cigarettes imagine how fun it would have been to to be in the rat pack but i think long after
00:51:11.300
all that has faded all that mystique from the 60s has faded what's going to endure is sinatra's singing
00:51:21.180
voice this is a voice for the ages for the centuries i think that people will still be listening to
00:51:28.260
sinatra uh centuries from now and why will they be listening because sinatra unlike listen there are a lot
00:51:36.920
great voices out there a lot of great voices on record and and and even today uh many wonderful
00:51:44.680
voices but sinatra had and still has in recording this absolutely unique ability to make you feel that
00:51:54.820
he was feeling these feelings as in the instant that he was singing these songs nobody else can really
00:52:02.580
do that and it is uh it is an intensely a definitively masculine voice and it is a voice that is filled with
00:52:13.780
and this is this is the key to the whole thing a completely acceptable frank made it acceptable
00:52:22.220
vulnerability frank created uh acceptability uh for uh for vulnerability uh in a man
00:52:32.460
he was a guy who could sing a torch song and really sell it because you thought he was feeling it he was
00:52:39.100
really feeling it while he was singing it and so it's not just macho it's not just swagger frank had plenty
00:52:46.780
of that and he can swagger with the best of them but it's this vulnerability and uh again this uh this
00:52:54.940
genius at conveying the feelings of these great songs that he sang that uh that
00:53:01.420
make men feel that it's okay to be vulnerable and make women feel this is a superbly masculine man
00:53:10.720
but this is a man who's not afraid of his feelings and that to women of course is a very very sexy
00:53:16.980
combination well james kaplan this has been a great conversation uh before we go where can people find
00:53:22.160
out more about uh your books on my wonderful website james kaplan.net uh they can read everything
00:53:31.420
about my two sinatra biographies my other books as well uh of course both books are on amazon
00:53:37.000
and uh and and i really want to thank you brett it is it's very seldom that i get to speak for so long
00:53:46.520
about this uh great artist and about this music that i love and it's clear you have a lot of the
00:53:51.700
same feelings for him and and so it's terrific to talk with you well thank you so much james thank
00:53:57.060
you brett my guest is james kaplan he is the author of the book sinatra the chairman and that's
00:54:02.400
available on amazon.com and bookstores everywhere really great read you can find out more information
00:54:07.100
about his work at jameskaplan.com and like i said at the beginning of the show if you want the show
00:54:12.200
notes for this podcast if you go to aom.is slash sinatra you'll find highlights links to people
00:54:19.620
stories we mentioned as well as a suggested frank sinatra playlist from james himself
00:54:24.320
well that wraps up another edition of the art of manliness podcast for more manly tips and advice
00:54:31.140
make sure to check out the art of manliness website at artofmanliness.com and if you enjoy
00:54:35.040
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00:54:38.700
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00:54:43.000
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