The Art of Manliness - #186： The Legend and Reality of Frank Sinatra

00:00:00.000 Brett McKay here and welcome to another edition of the art of manliness podcast old blue eyes

00:00:19.680 the chairman of the board the voice Frank Sinatra has been an icon of masculine coolness and swagger

00:00:25.300 for decades during his lifetime he was able to create a myth and legend around himself that

00:00:29.740 continues to exist today but like all legends when you look closer at them that you discover

00:00:35.620 that the reality is much more complex than the story we like to tell ourselves in the reality

00:00:40.420 of Frank Sinatra's life very very complex today on the podcast I talked to James Kaplan is about

00:00:46.360 his concluding volume of his definitive biography on Frank Sinatra it's entitled Sinatra the chairman

00:00:51.440 and on the show James and I discuss how Frank Sinatra's career was in the tank after World War

00:00:56.460 II and what he did to not only revitalize it but catapult himself into legendary status we also get

00:01:03.500 into Frank's foibles his incessant drive for power and how that connected JFK and the mob together

00:01:09.080 and we talk about Frank's enduring appeal as an icon of American masculinity a great show and when

00:01:17.000 you're done be sure to check out the show notes for this podcast at aom.is slash Sinatra you'll find

00:01:23.180 links to people and stories mentioned in this episode as well as a suggested Frank Sinatra playlist

00:01:28.200 from James Kaplan Frank Sinatra's biographer

00:01:31.100 James Kaplan welcome to the show

00:01:41.200 delighted to be here Brett thanks so much for having me

00:01:44.840 so uh your second biography or biography of Frank Sinatra came out last year and this

00:01:50.420 biography picks up it's called the chairman a subtitle and it picks up right after Frank Sinatra

00:01:57.680 won the academy award for best supporting actor for from here to eternity um well you talk about in

00:02:04.980 the book that before uh this this he won this award Sinatra's career was pretty much in the tank

00:02:12.140 and I'm curious can you give us a little backstory like how did Frank Sinatra going from making thousands

00:02:17.380 of bobby socks or you know sockers faint during the world war ii to you know people couldn't even

00:02:22.600 recognize them on the streets in new york city yeah well the uh the book that just came out was the

00:02:30.020 second volume of my biography of Sinatra second and final first volume was called Frank the voice

00:02:35.300 and covered his rise uh to incredible superstardom mainly during world war ii world war ii was really what uh

00:02:44.580 what jet propelled frank sinatra's career uh to its apex during those years because

00:02:52.220 in those in that time he was singing these ballads of yearning that so rhymed with the way the country

00:03:02.400 was feeling uh feelings of uh gentle sadness and and missing the boys who were away uh fighting overseas of

00:03:10.600 course frank was not away fighting overseas he had been classified 4f a lot of people suspected that

00:03:16.900 and called him a draft dodger but his records and and and william manchester who wrote a great history

00:03:24.220 of uh the armed forces in in south pacific in world war ii where he also served very bravely as a marine

00:03:31.060 uh said that sinatra was the most despised man in the armed forces uh because the all the all the guys

00:03:38.680 fighting overseas felt that the sinatra the draft dodger was back at home uh fooling around with 0.54

00:03:44.380 their women and in many cases they were right uh he wasn't a draft dodger he really did have a

00:03:49.160 punctured ear drum but the perception lingered despite the perception though he sold a ton of records in

00:03:56.580 world war ii after the war very very quickly things changed in america the political climate became very

00:04:05.420 conservative uh and the popular culture in america of america really became extremely conservative

00:04:12.800 after world war ii and tastes in popular music uh shifted gears just like that overnight suddenly

00:04:19.200 people were no longer interested in uh in the ballads of yearning suddenly the big band era which had

00:04:25.120 begun 10 years previously in about 1935 uh began fading away very quickly and america was in this odd

00:04:34.320 state of jubilation and fear jubilation because the war was over and fear because the rise of the

00:04:40.640 soviet union that accounts for the political conservatism and also i think the popular culture

00:04:46.140 too so uh popular music music really uh got pretty terrible in the wake of world war ii very quickly

00:04:55.520 there are a lot all kinds of novelty songs people wanted escape after world war ii so they were listening

00:05:01.060 to stuff like how much is that doggie in the window uh they and sinatra who was still recording for

00:05:07.540 columbia at that point uh but unlike many other uh unlike every other popular singer had enough power

00:05:16.420 to dictate what he could record still he decided to go along with the tide he were he tried to to he did

00:05:22.820 record a number of these uh crummy uh crummy uh crummy novelty numbers tennessee newsboy uh most infamously

00:05:31.460 this the worst record he ever made mama will bark his his career after world war ii uh went down the 0.99

00:05:39.680 tubes for a few reasons it wasn't just that tastes in popular music had changed uh it was really a

00:05:46.620 multi-determined problem and a lot of the problems frank created for himself uh he was in 1947 early

00:05:55.080 1947 he went to havana cuba to attend a mafia summit conference officially he went because he was there to

00:06:05.680 entertain all these top uh mobsters uh it's also been alleged over the years that he brought a suitcase

00:06:12.800 containing packed with cash for lucky luciano uh as tribute and he was cited in havana by a columnist

00:06:23.240 for the hearst papers uh and this columnist began to write uh disparaging columns about sinatra's

00:06:30.760 affection for the mob the hearst papers were very politically conservative again chiming with the times

00:06:36.740 frank frank frank frank was a dyed in the wool a liberal democrat he was an fdr democrat the hearst papers

00:06:43.800 hated him for that and suddenly they had something to call him out for well that wasn't enough for frank he

00:06:48.960 also uh and from the day he set foot in hollywood he began stepping out on his uh on his young wife nancy

00:06:57.780 uh with all kinds of holly hollywood uh starlets and uh in 1948 49 uh he stepped that up he was cited with

00:07:09.340 lana lana turner uh and then he began this famous affair with ava gardner and uh in 19 1951 his uh

00:07:20.680 his wife changed the locks on the house and divorced him but that wasn't all his record label columbia

00:07:27.420 dropped him because he wasn't selling records his movie studio mgm dropped him uh for various reasons

00:07:34.540 but they had gotten tired of him at that point his agents dropped him he wasn't selling records he

00:07:40.120 wasn't really making movies he married ava in 1951 but his his career was sinking just as fast as her

00:07:48.740 career was was rising and and uh as crazy as they were for each other frank and ava she began to get

00:07:56.100 sick of his moping around and uh so his marriage wasn't even working well then it was it was a

00:08:03.400 perfect storm of events and again frank himself had a lot to do with almost all of them so did he so he's

00:08:12.000 at the bottom of his career lowest of the lows from what you've read and researched about him did he

00:08:18.740 purposely like think okay i gotta do something about this i gotta do something to kickstart my career i mean

00:08:24.820 did he deliberately start thinking about how he could catapult himself back into constantly

00:08:31.160 constantly frank sinatra was the most important thing to frank sinatra throughout his entire

00:08:37.500 his entire working life from the time he first uh started singing professionally in his uh in his

00:08:45.180 very early 20s uh then went on the road with harry james and then tommy dorsey then went out on his

00:08:51.360 own as a singer uh through his decline into his comeback and until the very end of his singing

00:08:59.720 career the last concert he ever sang was in february 1995 after an incredible uh 60-year career

00:09:07.780 every minute of every day frank sinatra was thinking about his singing and about his career

00:09:14.920 that was his priority and so you can bet that during those years of decline he was obsessing

00:09:22.720 every waking minute about how he could come back easier said than done though easier thought about

00:09:28.780 than done he was incredibly frustrated incredibly depressed uh this is a period when uh he made uh

00:09:36.940 he made a couple of the first of his uh his three suicide attempts he was as low as you could get and

00:09:45.400 yes as you said before this is a point when he could walk through times square in new york

00:09:50.700 where in 1944 he had created a mob scene around the paramount theater with those with those fabled 1.00

00:09:58.900 bobby soxers uh he could walk unnoticed unrecognized sammy davis jr happened to be in times square

00:10:05.480 and saw frank walking through with his collar up and nobody recognized him wow so okay you said

00:10:13.460 that after world war ii the music uh tastes changed um during the 1950s but during the 50s is where a lot

00:10:21.860 of the albums that we listen to today you know came out a lot of the songs that he he recorded so

00:10:28.900 and it's kind of a weird time because like you said the big band era was over but yet rock and roll

00:10:33.180 was just starting so what did frank sinatra tap into that into the like the american taste in music

00:10:41.060 that people are like yeah this is great we like what he's doing how was it different from the big

00:10:44.780 band stuff and uh but how was it also different from like rock and roll well sinatra did more than

00:10:50.560 tap into uh sinatra really created a revolution in popular music rock and roll of course with its own

00:10:57.100 revolution in uh in uh in in in popular music rocket 88 that uh that historic uh cut was recorded in 1951

00:11:08.480 and rock and roll was on its way headed headed straight up elvis elvis would be walking down

00:11:14.440 the street in just a couple of years after rocket 88 and meeting sam phillips uh uh historically in in uh

00:11:22.260 at sun records in in uh in memphis but but sinatra created his own revolution in popular music it

00:11:30.960 wasn't it wasn't so much a tapping into let's let's step back a couple of years and remember that between

00:11:36.720 the end of world war ii and and around 1952 or 1953 people were just buying a lot of junk it was all

00:11:46.760 this very transitory transient ephemeral music that just kind of feel good uh doggy in the window and

00:11:54.780 and uh and mitch miller over at columbia had uh had sinatra uh recording these these crummy novelty

00:12:03.280 numbers and he had uh other great artists like rosemary clooney was recording recording mambo italiano

00:12:11.040 and come on to my house it was all very uh it was all kind of honky-tonk herky-jerky silly music

00:12:20.340 sinatra was dropped by columbia records they they failed to renew his contract in 1951 and he drifted

00:12:28.280 without a label for a couple of years in 1953 and the the importance of this cannot be overestimated

00:12:36.060 an incredibly uh farsighted young executive at capital records out in hollywood uh a young guy

00:12:44.160 named alan livingston decided to sign sinatra uh he signed sinatra because he knew that he knew how

00:12:54.220 talented incredibly talented sinatra was and he had some ideas alan livingston did he signed sinatra to

00:13:00.260 the standard artist beginning artist contract uh for for a sum in the three figures low three figures

00:13:08.020 i mean we're talking a couple of hundred dollars and when alan livingston told his capital record

00:13:13.180 sales force that he had just signed frank sinatra a room full of a couple hundred uh salesmen for

00:13:21.340 capital records they all groaned this guy was such a drug on the market at that point but

00:13:26.700 livingston's idea was he wanted to team this incredibly talented singer whose talent

00:13:34.140 livingston recognized despite how down on his luck frank was he wanted to team sinatra with a young

00:13:41.780 totally unknown uh arranger a guy named nelson riddle uh who i'm sure many of your listeners have

00:13:48.540 heard of but then nobody knew who he was frank sinatra didn't know who he was and uh

00:13:55.580 he teamed up sinatra with nelson riddle and uh they recorded a number uh very early in their

00:14:04.820 collaboration together called uh i got the world on a string and when sinatra heard the playback of

00:14:12.000 of that number that he just recorded with riddle's incredible arrangement because this guy could arrange

00:14:18.040 like nobody else sinatra said i'm back baby i'm back he knew it he knew it and he knew he had

00:14:25.520 it with nelson riddle and he and riddle began to turn out these singles and these albums

00:14:30.300 that uh that created uh as i said a revolution in popular music and let me just say one more thing

00:14:37.180 about that revolution because this is very important to understand we talked today about the great

00:14:42.080 standards uh cole porter irving berlin the gershwins all these the great american songbook all these

00:14:48.880 amazing numbers that stand the test of time so beautifully constructed that they that uh that

00:14:56.300 that modern uh modern artists keep recording them over lady gaga buble you know and people will 0.61

00:15:04.660 continue to record them for for decades and centuries to come because they are great and they're

00:15:10.360 classics sinatra was the one who really created the idea of the standard these songs were

00:15:18.860 not being recorded before sinatra insisted at the end of his columbia records career and at the

00:15:26.020 beginning of his capital records career in 1953 sinatra insisted on recording them when he performed

00:15:32.540 them in concert he would always credit the great songwriters so uh it's a long-winded answer brett to

00:15:39.120 your question but what i do want to say that it wasn't something that it wasn't sinatra feeling the pulse of

00:15:44.500 america sinatra was creating the pulse of america this was a great transformative artist who had uh who

00:15:52.960 had ears who had a a musical understanding on a mozartian level and knew what he wanted to do with

00:16:01.100 popular music and and uh created a revolution yeah that kind of leads to my next question uh because i

00:16:06.460 thought it was interesting a lot what i love about your book james is that you you take us into these

00:16:10.540 recording sessions and uh talk about the the dynamic between sinatra and the the arranger and the the

00:16:18.060 uh or the orchestra and i think it's interesting i think maybe a lot of people today um think of

00:16:24.300 sinatra as like pop stars of today that you know he had a nice voice and he just goes in and sings the

00:16:28.920 songs that the music the musicians wrote and that's it but the way you describe the the recording sessions

00:16:35.760 like sinatra was like almost a conductor uh almost and he was making these little improvisations

00:16:41.420 and he could just tell right away that we need to like you know the violins need to do this

00:16:45.260 so i mean was he different from some of the other popular crooners in the uh during the time because

00:16:51.720 of his musical ability yes he was absolutely different uh he this was a musical genius uh this was a guy

00:17:01.200 who knew exactly how he wanted those recordings to sound we talk about record producers uh the great

00:17:09.000 george martin just died a couple of uh days ago and a great great producer and uh producers today uh

00:17:17.340 people like niall rogers and pharrell williams these are people who go into a studio and shape every

00:17:24.540 every every bar of every song every second of every every track that that uh that's recorded

00:17:31.680 sinatra had people who were called producers but sinatra really produced all his own albums and all

00:17:38.860 his own singles he was the guy who knew exactly how he wanted these records to sound he was the guy who

00:17:46.200 had such incredible ears that if the third violin in his orchestra and sinatra by the way was a guy who

00:17:53.000 revered musicians he he never wanted to be in an isolation booth singing uh when he was recording

00:17:59.280 he always wanted to be out there with the musicians if the third violinist was a half note off he would

00:18:04.480 look he would stop the music and freeze the guy with uh with a glare from those electric blue eyes and

00:18:11.120 say where you working next week sinatra knew exactly how he wanted these uh these songs to sound and

00:18:18.480 despite the fact that this is a guy who who really couldn't read music he he he he couldn't read he

00:18:25.880 still knew his way around a score and so he could say uh bar 45 uh shouldn't that be maybe an f natural

00:18:33.720 instead of an f sharp he knew stuff like that and we also have to remember that these songs he was

00:18:40.160 recording unlike the songs of today all came from written arrangements these were uh these were charts

00:18:48.120 these were very detailed uh arrangements that were written by great arrangers such as riddle and billy may

00:18:56.880 and uh and uh uh sinatra worked with dozens of terrific arrangers up to quincy jones and klaus ogerman and

00:19:08.480 don costa and uh gordon jenkins these were all brilliant men uh with whom sinatra

00:19:17.280 purposely allied allied himself he he hired these guys because he knew what they could do for him but

00:19:23.600 sinatra was the boss right so i mean i love sinatra's music i mean i listen to uh serious sinatra on

00:19:30.900 a serious f you know xm radio all the time um but the thing that i've always been conflicted about the

00:19:38.640 guy because he's like an extremely complex character uh super talented i love his music but then

00:19:44.840 you do such a great job in the book painting this the complexities of sinatra i mean like the man had

00:19:50.360 a lot of paradoxes about him and as you said earlier some of these uh sort of the the darker side of

00:19:56.860 sinatra uh caused him problems with not only his family life his love life but also his career so can

00:20:03.500 you talk about some of these personality paradoxes and and how that affected friendships uh business

00:20:10.020 associates and even uh his his lovers and his wife and ex-wives yeah uh yeah this was well there there

00:20:18.360 are a few things you have to talk about when you're talking about sinatra's personality he was as you say

00:20:24.200 this was a musical genius uh but he was also a guy who could uh who also uh also had a genius for

00:20:32.380 making himself dislikable and i spent 10 years writing these two books about sinatra and there were a lot

00:20:38.080 of times when i disliked him when i was writing about him but i never got bored with him uh he wasn't he

00:20:44.140 was never boring uh there are a few things you need to talk about when you talk about the demons that

00:20:49.600 were inside sinatra one one big one was his mother uh his mother was named dolly sinatra she was a 0.99

00:20:56.480 volcano she was under five feet tall little tiny woman who was brilliant uh swore like a sailor 1.00

00:21:03.720 uh uh she was a democratic party organizer in uh in hoboken new jersey where frank grew up she spoke

00:21:12.360 every dialect of italian when she went around hoboken getting out the vote for franklin delano roosevelt

00:21:18.840 uh she was she was volcanically she had a volcanic temper she has she was uh pathologically impatient 1.00

00:21:27.060 and sinatra in many ways was the same person as his mother but this was a mother who

00:21:32.960 sinatra later said he never knew whether she was going to hug him or hit him and that was literally

00:21:37.660 true she he was never certain of his mother's uh love for him and that really conditioned his

00:21:45.060 relationships for the rest of his life especially with women his daughter younger daughter tina sinatra

00:21:50.400 wrote a wonderful memoir and and wrote in her book my father was a deeply feeling man who was unable to

00:21:57.140 attain an intimate relationship with another human being and that included all the many hundreds

00:22:02.760 if not thousands of love affairs he had he he he loved women in a lot of ways but he never really

00:22:11.040 loved it was very very difficult if not impossible for him to be intimate with somebody else okay so then

00:22:18.600 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

00:22:26.320 musical genius he said in later life that when he was walking around as a kid he heard the music of

00:22:32.120 the spheres well that sounds very high-flown and exaggerated but i think it was literally true this

00:22:38.240 is a guy who heard sounds in his head that other people didn't hear and so there he is walking around

00:22:43.720 hoboken new jersey in the 1920s in the 1930s a very tough town where if an italian kid walked across 0.77

00:22:49.920 the the wrong street into the irish neighborhood he'd get the crap beaten out of them uh and uh this

00:22:56.920 was a kid who was a genius that was not easy to walk around with uh so he kind of had to keep that 0.89

00:23:04.200 hidden all his he was a highly highly strung guy very oversensitive he had to keep that hidden he he

00:23:10.580 wanted to he he always wanted to seem tough that was that was important in hoboken when he was a kid

00:23:16.040 it was important when he had grown up and the toughest guys of all when he was growing up in

00:23:21.340 hoboken the 20s and 30s as an italian american kid when italian americans uh one of the things i

00:23:29.280 learned writing writing these books uh it's it's easy sometimes to sort of feel this reflexive

00:23:35.460 nostalgia for the way america used to be oh things were better in the old days when men were men and 0.90

00:23:41.260 women were women and you know some of that's true uh there was a lot that was very bad in this 0.99

00:23:47.000 country in the old days and the the very worst thing that i found was this very easy reflexive

00:23:53.980 uh racism that existed in this country uh there's still a lot of it around but there was it wasn't

00:24:01.680 even questioned in those days if you were a white anglo-saxon protestant male uh you could and you had

00:24:07.780 some money you could uh you could be in the ruling class if you didn't you were out of luck and italian

00:24:13.460 americans were just a half a step above uh african americans on the social scale and italian americans

00:24:20.200 like african americans were looked on as happy singing dancing people uh and and and also uh who now 0.55

00:24:29.420 and then uh murdered people right they were they were either clowns or they were mobsters and that was

00:24:34.480 that was rough for frank to live with but he as soon as he began performing in clubs he began running

00:24:41.360 into these guys who ran the nightclubs in those days and they were the mafia the mafia ran the nightclubs

00:24:49.000 and and a lot of them were italian america italian american the mobsters uh and and frank uh idolized

00:24:57.180 these guys they were men of power they were men of strength and he saw them incorrectly but he felt

00:25:03.060 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

00:25:11.340 strung and oversensitive and a musical genius and whose mother didn't really love him and boo-hoo that

00:25:17.180 sounds sad but if it happens to you it's real and it happened to him he couldn't really form an intimate

00:25:24.080 relationship he was too highly strung and once ava threw him over ava gardner threw him over in the 1.00

00:25:30.000 early 50s he began to drink pretty seriously alcohol became a big part of his life and he was a mean

00:25:36.100 drunk he was an angry drunk and he had all these demons inside and when he drank the demons would come

00:25:42.320 out so there is a there's an answer to your question there are an awful lot of things inside sinatra that

00:25:49.900 were bugging him and uh and they could make him behave very badly right i mean going back to uh the

00:25:57.500 volatility i mean you had these you describe encounters where you know he would go after men

00:26:02.640 who were like twice his size there was an encounter where he went after uh john wayne

00:26:06.340 yeah the parking lot unbelievable frank sinatra was five foot seven five foot seven in the stocking feet

00:26:12.900 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

00:26:21.520 little man with thin wrists and and delicate hands but he had this volcanic temper same as his mother did

00:26:29.240 he was pretty fearless and when he was in his cups when he had a couple of drinks in him and he was

00:26:35.380 feeling angry about something yeah i mean he went right up against john wayne uh and you're talking

00:26:42.360 about a guy who was six foot four and who was a genuine tough guy uh frank frank wasn't afraid uh for a

00:26:49.740 second standing in front of john wayne and john john wayne uh didn't want to fight frank sinatra it

00:26:56.180 wasn't that he was scared he just didn't want to fight him uh to his credit right yeah and i thought

00:27:00.840 it was funny i mean the circumstances of the fight was there's a dose of irony to it because it was like

00:27:06.100 a party and then vegas and benefit and sinatra was dressed like a indian squaw yes he was it's in the

00:27:14.120 old politically incorrect terminology yes yeah i'm not allowed to say that anymore right exactly that

00:27:19.640 that's how he was dressed that's how that's how you say indian woman uh native american woman and

00:27:24.040 and there's wayne the duke with his uh he's six foot four in his stocking feet and he's got on the

00:27:31.100 cowboy hat which makes him about six foot nine right and there they are facing off in a parking lot yeah

00:27:38.760 so yeah this these this this personality of sinatra so he had the mother the issues with his mother and

00:27:45.300 this volatile and it seems like yeah he had a chip on his shoulder uh being an italian american and he

00:27:49.940 was talented and he knew it um and so it kind of the theme that you actually that you you see throughout

00:27:57.420 the book and i think all these these three things come together with is that sinatra was very interested

00:28:03.440 in power uh not only in business but it also carried over he wanted to get into the political

00:28:09.620 arena we'll talk a little bit more on his relationship with uh jfk but what did he do i

00:28:16.880 mean why was he obsessed so obsessed with power and what did he i mean did he have like some common

00:28:20.560 tactics or power pulleys that he would use on people to get what he wanted well power was always

00:28:29.240 important to him from the beginning again this is a guy who as a kid had felt himself to be weak had

00:28:36.700 felt himself to be one down as a small person as an italian american as a as a guy who knew he had

00:28:45.400 the goods to become the best popular singer of all time uh but at first nobody knew it but him

00:28:52.920 uh this is a guy who had to uh learn to throw his weight around power was very important to him

00:28:59.000 commercial power the power of his career uh when he first uh when he first broke through after he

00:29:06.520 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 1.00

00:34:40.320 beautiful women and john kennedy from an early age wanted to score with every last one of them much 0.85

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 0.99

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 0.87

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 1.00

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 0.90

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 0.86

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 this podcast and have gotten something out of it i'd really appreciate it if one you could tell your

00:54:38.700 friends about it spread the word about the show but also give us a review on itunes or stitcher

00:54:43.000 that helps us out a lot as always i appreciate your continued support and until next time this

00:54:47.900 is brett mckay telling you to stay manly

The Art of Manliness - March 25, 2016

#186： The Legend and Reality of Frank Sinatra

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