“The Way You Felt When You Were 20”: Talking Rat Pack with Karina Longworth

WE TEND TO imagine the Rat Pack through a nostalgic haze: cocky guys in great suits, singing, dancing, yakking it up, and generally having a killer time in the spotlight. Karina Longworth’s hit podcast, You Must Remember This, delves deep into the lost, misunderstood, or forgotten histories of Hollywood, and, in its most recent season, takes us through the life and work of Dean Martin and Sammy Davis Jr., shedding necessary light on some of the darker aspects of the Rat Pack’s glamorous legacy.

Dean and Sammy were part of what Sinatra called “the summit at the Sands” — when he wasn’t calling it “the Clan,” over Sammy’s objections — and the two shared stages for years. Their places in the Rat Pack hierarchy were defined in unequal terms, Longworth explaining:

Dean would be perceived as Sinatra’s sidekick, but privately Dean was his own man. If Frank wanted someone around who he could control, he’d call Sammy. Frank saw Sammy as his little brother and had genuine affection for him, but onstage he spent decades hazing Sammy as though he was the runt of the frat.

Dean Martin was born Dino Crocetti in Steubenville, Ohio, and he spoke only Italian until he was five. Italians (especially immigrants) were the Other to a postwar audience, which provoked Martin to change his name and get a nose job. Longworth explains that his lovable lush persona was mostly just an act. It was usually apple juice in that ever-present glass instead of scotch. Martin discreetly tossed his drinks into a potted plant when partying with the volatile Sinatra. Apparently, Martin’s greatest passion in life wasn’t booze or music or friendship but golf. He’d wake up early to get a quick round in before his workday began. Martin shined as the struggling drunk in Howard Hawks’s great Western Rio Bravo, but it’s an open question whether Martin possessed secret depths, or truly content to swan through his life in the public eye with seeming effortlessness.

In Longworth’s history, Sammy Davis Jr., in all his affable insecurity, functioned as the polar opposite of cool, aloof Dean Martin. “Dino” was welcomed everywhere and barely wanted to be anywhere; Sammy fought hard for a modicum of the attention and admiration that came so easily to his fellow Rat Packer. The Harlem-born Sammy Davis Jr., half African American and half Afro-Cuban, tended to play along with disrespect from Sinatra and their buddies, which tended to come in the form of racist jokes at roasts and public gatherings. Later, Davis would tell a Chicago radio show that, while he loved Sinatra, who had been extremely kind to him after he lost his eye in an infamous car accident, he had issues with the subservient role he was forced to play.

Longworth explores the various roots of his Davis’s neediness — parental neglect, being drafted into the Army and stationed in Wyoming of all places, facing down bullies his whole life. The diminutive Davis survived his detractors, not to mention his own poor financial and political choices (publicly embracing Nixon in 1972), by his wit and charm, doing impressions, eventually winning over numerous hostile audiences. As he once put it: “My talent was the weapon, the power, the way for me to fight. It was the one way I might hope to affect a man’s thinking.”

By telling the stories of these two beloved if campy figures, Longworth sketches a vivid, penetrating, and novelistic portrait of lost midcentury manhood, always acutely aware of character and motive, putting that iconic martini-swilling, skirt-chasing, toxic masculinity in its place.

I talked with Longworth through Zoom about the Rat Pack, postwar American manhood in crisis, the novel Some Came Running, Jerry Lewis’s heartbreaking phone call with his old comedy partner, whiteness and race, capitalism, and the Italian term for being someone “who simply does not give a fuck.”

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MATT HANSON: What made you want to do this season of You Must Remember This about the Rat Pack?

KARINA LONGWORTH: Well, I don’t really think about it as being about the Rat Pack. It was really about these two guys and the fullness of their lives and their careers outside of the Rat Pack. I like stories where you can talk about two people who have similarities and differences. I did the seasons with Bela Lugosi and Boris Karloff, and with Jean Seberg and Jane Fonda.

In some ways, it seemed like Dean Martin and Sammy were two pieces of a puzzle that fit together. And I had read this book by Nick Tosches a few years ago, Dino: Living High in the Dirty Business of Dreams (1992). It’s one of the best biographies of a famous person that I’ve ever read. The thing that makes it so great is that it’s not just about Dean Martin; it’s about America, it’s about the immigrant experience, the mafia, and about how close the business they do is to what we would consider “legitimate business.”

I just kept returning to these ideas, especially during the Trump administration and the disastrous handover of power after he did not win the second term. I was just sort of thinking about how we think we live in a society of rules and, really, we don’t. There’s this very uneasy balance between the things that we consider to be criminal and the things that we consider to be legitimate. At the end of the day, you know, it’s just all capitalism.

I never realized that Dean Martin was basically trying not to be seen as Italian for a period in his career. The nose job, the name change. He’s trying to be more “white” or whatever that meant at the time. With Sammy, he pretty much allowed his friends to make his Blackness into a punch line. I mean, sure, people did things differently back then, but hearing the kind of racist jokes they told about Sammy at the Friars Club roasts is pretty raw. Could you say a little more about how race factored into Dino’s and Sammy’s self-presentations?

Yeah, that’s kind of the subject of the whole season. Certainly, in the last couple of episodes, things are going to get really complicated for Sammy, because he went through this period from the mid-’60s on where African Americans were more empowered in the culture, and a lot of people started to see Sammy as being an Uncle Tom figure. He basically spent his entire career trying for white approval, because he thought that was the only way to have success in the entertainment industry.

Then the younger generation was saying, “Why are you tap dancing — like, literally tap dancing — for white people? Why are you literally tap dancing for Frank Sinatra’s approval? Why don’t you represent being a Black person?” And so Sammy was kind of damned if he did, damned if he didn’t in a lot of ways.

For Dean Martin, his race was very problematic in the late 1930s and early ’40s, so that’s why he changed his name from Dino Crocetti to Dean Martin, and that’s why he got a nose job, and that’s why he tried to downplay being Italian. But by the ’60s, mostly because of the rise of Frank Sinatra, being an Italian American meant something different culturally. So, he started recording albums that were entirely of Italian songs. These were very cheesy and almost parodies of the Italian American experience, like “That’s Amore,” and it became a part of his identity, and he could make a lot of money off of it.

Growing up in the ’90s, when there was a bit of a Rat Pack revival, I watched mob movies like Goodfellas, and it surprised me how some of my Italian American friends were turned off by mob movies. I never really realized how much anti-Italian prejudice there was at a certain point in American history. In John Steinbeck’s novel The Winter of Our Discontent, the main character considers using the Sullivan Act, a law specifically targeting Italian immigrants, against his Sicilian American boss.

I have two points that I want to make about that. One is that Frank Sinatra absolutely flaunted his association with the mafia, and he never really stopped doing that. In the ’80s, when the Rat Pack did this big comeback tour, he started speaking in the more politically correct terms and it was clear that he was trying to be more of a diplomat. He was doing these press conferences with Dean Martin, and Dean was telling the same old jokes from the ’60s, which was kind of a disaster. Still, Sinatra considered [mobster] Sam Giancana one of his best friends.

And there’s this Rat Pack movie called Robin and the 7 Hoods, which is the Robin Hood story set in Prohibition-era Chicago. That whole movie is Sinatra’s love letter to his Chicago mobster friends. And he started singing “My Kind of Town” about Chicago as a tribute to them. That’s one reason why some people don’t like Frank Sinatra. Certainly, when I wrote a book about Al Pacino, I encountered some of this talk as well, which is like, especially with The Godfather movies, Why are Italian Americans presenting us in this way?

On the other hand, you have Dean Martin, who seems to have understood pretty early in his career that ultimately the mafia knew how to do business better than supposed “legitimate” business, and that, and at the same time, America would always be racist against Italians to some extent. So he figured that, as an Italian American, he could never be allowed into the sort of inner circles of WASP power. Maybe the best he could do would be to make a lot of money and then be left alone, so that’s what he strove for.

Sinatra really thought he could have it both ways: he thought he could pal around with the mafia and use JFK as an entrée into the absolute inner sanctum of legitimate American power. When he was ultimately shown the door by the Kennedys, he ultimately switched gears and sort of found that door in through the Reagans.

At one point, you talk about James Jones’s novel Some Came Running, and the movie version which stars Sinatra, Martin, and Shirley MacLaine. There’s a lot of postwar art about men who were traumatized from the war and then trying to come home to adjust to normal, everyday life after an experience like that. We’re used to hearing about the greatness of the Greatest Generation. I wonder why we don’t think about how much the experience of the war and how seeing that kind of evil and horror up close really traumatized a generation.

Yeah, I think that you really get a feeling of that from Some Came Running. I don’t think many people really read that novel anymore; I think the movie has really supplanted it in terms of public awareness. The novel was originally published at something like 1,600 pages, it was really heralded because Jones’s earlier book, From Here to Eternity, had been such a success as both a book and as a movie. Some Came Running was kind of a flop and pretty quickly disappeared from print. Sometime over the past twenty years, Jones’s daughter supervised a rerelease of the book, which is more like 1,200 pages. I definitely recommend the novel if people are interested in this period at all. It’s a commitment, but there’s an ebook and an audiobook available, and I think it’s really great and really worth it.

The movie is actually a really good adaptation of the book, based on what you could do in Hollywood in 1958. But the book goes deeply into the thing you’re talking about — exploring the veteran’s psyche — and that’s why I brought in passages of the book into the podcast. I felt like it was a much more literal way of talking about these ideas from movies like Some Came Running and The Young Lions. And even, to some extent, this applies to Rio Bravo in terms of how it deals with a masculinity crisis.

This psychological hangover from World War II ends up being pretty important when you’re trying to figure out how you get from this cultural moment of prewar, during the war, through to Dean and Sammy, who are basically nightclub stars. How do you get to the early ’60s when they’re making these Rat Pack movies?

So, the Rat Pack ends up becoming very popular because of this feeling that’s in the movie Ocean’s 11, which I talk about. It’s about these guys whose glory period was about 1944–1945, trying to have a resurgence 15 years later as middle-aged men. So I think the Rat Pack appeals to guys who were in that same situation.

Maybe they fought in the war when they were in their late teens or 20s. Fifteen years have passed, and they haven’t really dealt with anything that happened on the battlefield and how they felt about it when they got back. The 1950s American culture was just, like, Go make babies and buy refrigerators and buy a new car. People weren’t encouraged to talk about what was going on inside them, so they still have a lot of darkness boiling inside that they need to burn off.

The Rat Pack gives them a way of saying: “You’re not getting older, don’t worry about this stuff that you’re worried about. You can just have a drink, and listen to music, and be around beautiful women, and none of this matters.” That was something I didn’t really understand until I was watching all these movies consecutively and I read that novel.

So, it’s almost like a prolonged adolescence, like a Peter Pan feeling? We don’t have to grow up, we can just hang out and drink and chase women — being boys, essentially.

I don’t think it’s a prolonged adolescence; I think it’s a reversion. It’s like we all went through this thing and then we were hustled straight from the battlefield and into these adult lives as husbands and businessmen and consumers. So I think it’s actually a pretty common generational thing of being in your 40s and wanting to return to the way you felt when you were 20.

I haven’t read the Nick Tosches book, but I have heard that the term Tosches uses to talk about Martin in the book is menefreghista, which apparently can be translated as “one who simply does not give a fuck.”

Obviously, we can’t look into Dean Martin’s soul, but I wonder if you get the impression that Martin really didn’t care about anything, or if there were some emotions there that he was trying to hide. I’m thinking about the way he reacted to the death of Marilyn Monroe, which he seemed to feel a little raw about at the time, specifically the way she was callously passed around by the guys.

I think the people who knew him, who had the closest position to him, were consistently frustrated about how unknowable he was and how little he gave them emotionally. So you can’t look into his soul, but there were so few times when he made it clear that he cared about something. And one thing I talk about is his reaction to Marilyn Monroe’s death. His kids, his wives, they all constantly talk about how they were trying to get something out of him emotionally and they couldn’t get anything. [Comedy partner] Jerry Lewis wrote two full books about how he didn’t just love Dean, he was in love with Dean — he was obsessed with Dean — and Dean wouldn’t give him what he needed back.

There’s that mortifying moment when Jerry calls him late at night on the phone and says something like, “I’m glad that I work with you, Dean,” and all Dean says is something like, “All I see when I look at you is dollar signs.” 

Yeah, Jerry is basically saying, Hey, for all of our problems, I think our act worked and we’re a good team because we love each other. As I say this in the podcast, I think Jerry got a harsher response precisely because he tried to make it emotional, because he used the word love. That is a sure-fire way to get Dean to put his defenses up. To me, that’s why Martin says, “There’s no love, to me you were nothing but a dollar sign.”

Especially with Dean, I think Jerry wanted to be seen as someone who was handing his heart over to Dean on a silver platter, and Dean was crushing it. I think it’s a beautifully written scene because Jerry’s like, maybe I can’t be sure Dean said he loved me back; maybe this is just what I wanted to hear.

And as far as Sammy is concerned, he’s got all this talent, and at the same time he just has to kind of take Frank’s shit. It is a very interesting place for him to be in, isn’t it? It’s one thing to just be a hack for Sinatra to make fun of all day, but it’s another thing to be talented but so in need of love and approval that you have to settle for less. Maybe Sammy was the Jerry Lewis to Sinatra’s Dean Martin.

I think with Sammy, maybe he just felt lucky to be there. Again, it’s this issue of how fast culture was changing and how fast it changed without him really understanding. And so, in 1960, on the stage in Las Vegas, he is lucky to be there in a sense, because he’s the only Black performer on a stage with white performers, not playing a butler or doing a Stepin Fetchit act.

Even if they’re making fun of him, if they’re doing literal KKK jokes at the Sands in Vegas, they’re also letting him sing and dance and show people everything he can do. But by 1964–1965, he’s being perceived, just the fact of being onstage with Frank and Dean, he’s being perceived as somebody who is playing to the white gaze when he doesn’t have to.

I think it’s very unfair, but I can at least see the point. At that moment in American history, the Black community might really want to draw a sharp distinction between past and present and need to get to a place where the white audience realizes that you’re a musician, a virtuoso, and that you’re not here to entertain the white audience’s preconceptions.

You have to understand, too, how people internalize things. So, to some extent, Sammy had internalized the racism of the industry that he worked in. He was so used to having most of his income come from a Vegas that was so racist — I mean, for so long, he wasn’t even allowed to have a drink at the bar of the casino that he was performing in. Sammy was so used to that that when things in the culture changed very rapidly, he was still stuck in this mindset of, Well, I can’t do anything to piss off the casino owners, or the patrons from Mississippi, because otherwise I won’t have that source of income. And he really needed the sources of income that he could get.

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Matt Hanson is a contributing editor at The Arts Fuse. His work has appeared in The American Interest, The Baffler, the Guardian, The Millions, The New Yorker, The Smart Set, and elsewhere.