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Frank Sinatra 101: Your Guide to the Iconic Singer’s Most Pivotal Film Roles

The Chairman of the Board is on the Mount Rushmore of the 20th century’s greatest vocalists. But he never stopped aspiring for movie stardom, which led to Oscars, some classic performances and a few cringe-y moments.

In 1963, Frank Sinatra tried to explain his day job. “I don’t know what other singers feel when they articulate lyrics,” he said, “but being an 18-karat manic-depressive and having lived a life of violent emotional contradictions, I have an overacute capacity for sadness as well as elation. I know what the cat who wrote the song is trying to say. I’ve been there — and back. I guess the audience feels it along with me. They can’t help it. Sentimentality, after all, is an emotion common to all humanity.” 

His genius at imbuing a song with his very essence — living its emotions in real time as his baritone made them beautiful — is why the Chairman of the Board is considered one of the great singers in all of popular music. Dying in 1998 at the age of 82, Sinatra was a bundle of juxtapositions — bighearted but also jealous and petty, a lifelong advocate for social justice but also a womanizer and a misogynist — which, of course, only made his performances that much richer. He made songs come alive because he was so vibrant and unpredictable himself.

But Sinatra also wanted to be an actor, an art form for which he wasn’t nearly as naturally gifted. Yet his capacity to convey feeling served him well, and his best film roles seemed to be a way for him to communicate something deeply wounded inside. His daughter Nancy later recalled that Burt Lancaster, his co-star on From Here to Eternity (which was shot during a personal low point for Sinatra), observed how Sinatra translated personal pain into his performance: “His fervor, his bitterness had something to do with the character … but also with what he had gone through the last number of years. A sense of defeat and the whole world crashing in on him … they all came out in that performance.” Those depths led to him winning an Oscar for the part.

So where do you start if you want to study Sinatra’s film work? 

I’ve put together a chronological tour through his movies, focusing on the highs but also spotlighting a few marginal efforts that, nonetheless, say something about him as an actor. What you’ll notice is that the man represented a certain kind of swaggering, hip masculinity that would eventually no longer be in fashion — and that Sinatra wasn’t always able to shift with the times. Beneath that incredible voice was a lot of hurt and vulnerability — you could sense it in his music, and it’s absolutely evident in his imperfect, often fascinating movie career.

The House I Live In (1945)

From the start of his professional life in the 1930s, Sinatra believed that entertainment could change hearts and minds. Writing to screenwriter Albert Maltz in 1945, moved by his work on Pride of the Marines, a biopic of World War II hero Al Schmid (who went through a difficult rehabilitation after the war), the singer gushed, “I’m completely convinced that the greatest, most effective weapon has suddenly come to life for the millions of bigoted, stupid, anti-everything people. I’m sure that they have read it in books and newspapers and I’m sure they’ve heard it on their radios, and I’m also sure that they have been talked to — but I tell you, Albert, this is it — just plain movies. You’ve got to hit ‘em right in the kisser with it and, baby, you really did.”

The two men collaborated that same year on a short PSA that preached religious tolerance. The House I Live In starred Sinatra as himself, stepping out from a recording session to stop a group of kids from beating up a Jewish boy. Sinatra teaches them that prejudice is bad, and that all that matters is they’re all Americans. The film is syrupy — and also a little closed-minded in its own way, with Frank using a three-letter ethnic slur to disparage the Japanese we fought in World War II — but despite its clumsiness, Sinatra demonstrated that he wasn’t afraid to use his celebrity to attack bigotry, a cause he’d take up for the rest of his career.

On the Town (1949)

Sinatra’s first starring vehicle was 1944’s Step Lively, but his first memorable role didn’t occur for another five years, when he reunited with Gene Kelly (his co-star in Anchors Aweigh and Take Me Out to the Ball Game) for this carefree musical comedy about three sailor chums in New York City for a day, looking for love. And despite his reputation as a lady-killer, Sinatra played Chip, the nerdy guy in the group who’s almost more interested in being a tourist than in courting the dames.

It’s a good look for the singer, who’s charmingly dorky. But when the cameras weren’t rolling, it was clear who the big dog was. Kelly, who co-directed On the Town with his future Singin’ in the Rain partner Stanley Donen, recalled, “Those were his famous days, and he was as hard to hide as the Statue of Liberty. He was always being mobbed. To get around that problem, we decided not to hire any limousines. Instead, we hired Yellow taxis. We would push Sinatra on the floor of the taxi … so that the taxi would seem empty. No, he didn’t like that.” 

From Here to Eternity (1953)

This Oscar-winning drama, based on James Jones’ novel, was a highly sought after project, with plenty of big actors supposedly in the mix. At that point, Sinatra’s personal and professional life were at a low ebb — he was in the midst of Divorce No. 2 and his musical career had stalled — but he landed the part of Maggio, an army private stationed in Hawaii in the months before the bombing of Pearl Harbor. From Here to Eternity was a way back for Sinatra, and he wasn’t going to let it get away. As infamous gossip columnist Hedda Hopper wrote at the time, “His manager assured me that, despite the printed report, Sinatra was not gumming up the deal by holding out for too much do-re-mi. When he wants a part badly, as he does this one, Frank considers money of secondary importance. … [T]he Eternity role could open up a completely new phase to Sinatra’s acting career.”

Her words proved prophetic: As the wisecracking but sensitive Maggio, Sinatra showed a vulnerability and depth he hadn’t been able to convey on screen to that point, as his character is tormented by the cruel staff sergeant (Ernest Borgnine), who eventually tortures him to death. Most remember From Here to Eternity for its iconic kiss on the beach between Burt Lancaster and Deborah Kerr, but Sinatra’s supporting role revitalized his film aspirations, earning him a Best Supporting Actor Oscar when he was 38.

“Ladies and gentlemen, I’m deeply thrilled and very moved,” he said after receiving raucous applause at the Academy Awards, “and I really, really don’t know what to say because this is a whole new kind of thing. You know … [I do] song-and-dance-man type stuff.” He’d go on to host the Oscars in 1963.

The Man With the Golden Arm (1955)

Sinatra was determined to get the role of Frankie, a heroin addict just released from prison who wants to leave the junk behind. The only obstacle was Marlon Brando, who was also interested and had beaten him out in the past for parts. (In the deeply mediocre Guys and Dolls, Brando ended up in the Sky Masterson role, which would have been better for Sinatra, who was relegated to playing the other lead character, Nathan Detroit.) And so, even though Sinatra received just a portion of the script for The Man With the Golden Arm, he didn’t hesitate to say yes. “I got a call the next day from Sinatra’s agent, who said, ‘He likes it very much,’” said the film’s director, Otto Preminger. “I said, ‘All right, I’ll send him the rest of the script as soon as I have it.’ He said, ‘No, no. He wants to do it without reading the script.’”

The film earned Sinatra his only Best Actor Oscar nomination, and it’s an impressively anguished performance. In subsequent years, Hollywood would offer plenty of big-screen versions of drug withdrawal, but Sinatra’s cold turkey remains suitably haunting. And the Chairman thought pretty highly of his work as well: Around that time, he said in an interview, “I find myself picking whatever I do apart, which I do believe is quite healthy, and I found that after seeing The Man With the Golden Arm, I was as contented with that performance as I’ve been with anything I’ve ever done in my life.”

Pal Joey (1957)

Want Sinatra as sex symbol and epitome of 1950s masculinity in all its complexity? This big-screen version of the racy musical — which concerns a cad, Joey (Sinatra), engaged in an affair with a rich older woman (Rita Hayworth) he wants to bankroll his nascent nightclub — is pure Sinatra, singing indelible tunes like “The Lady Is a Tramp” while showing off his devilish charm. (To demonstrate his softer side, Joey actually has real feelings for a pure-hearted singer, played by Kim Novak, his Man With the Golden Arm co-star.)

Depicted as endlessly desirable and dreamy, Joey was a perfect Sinatra vehicle, letting him seem classy and a bit sexist at the same time. (Joey’s philosophy: “You treat a dame like a lady, and treat a lady like a dame.”) That attitude can make Pal Joey feel like a relic. (As film critic Richard Lippe put it, “Pal Joey endorses Sinatra’s manipulation and exploitation of women.”) As a result, the movie’s sexual gamesmanship can be cringe-inducing at times, but it’s an expert entertainment that accurately conveys what was considered suave and sophisticated for its era. (And he won a Golden Globe for the performance.)

Some Came Running (1958)

Maybe you can’t go home again: That was the theme of this Vincente Minnelli character study, in which Frank Sinatra played Dave, a World War II veteran and a drunk, who finds himself back in his small Indiana town, hoping to impress the locals with the fact that he’s a novelist. Some Came Running doesn’t have much nice to say about Real America, and the star was equally dismissive. In a Time profile written during the film’s making, Sinatra (who himself was drinking heavily) declared, “This place is worse than skid row in Los Angeles,” and would comment to himself, “Look at that ugly broad over there. Hello, you horrible bag,” when surveying the Indiana natives in the town where the film was shot.

Nevertheless, Sinatra is a wonderful heel in Some Came Running — bitter and full of self-loathing — and he’s terrific alongside Shirley MacLaine, who plays Ginny, a bighearted, not-very-bright woman who unreservedly loves him. It’s a movie about the difficulty of reinventing yourself, and Sinatra does a good job as a son of a bitch who’s stuck with himself. And it’s fun to see him and his Rat Pack pal Dean Martin in serious roles, although they were playful on set. “They did exactly what came to them at the moment,” MacLaine said, later adding, “They loved it when things would go wrong, and then they could really be themselves, to show the audience that they actually were real.”

Ocean’s 11 (1960)

You know how remakes are always worse than the original? Ocean’s 11 is the great exception: The 2000s films from Steven Soderbergh, George Clooney and Brad Pitt have more laughs and ingenuity than the 1960 movie that inspired them. But the Sinatra film, in which he teamed up with pals Martin and Sammy Davis Jr., has its goofy charms. What saves the picture is that no one takes the convoluted heist plot seriously — it’s merely an excuse for the actors and the audience to spend some time together.

But you could also read Ocean’s 11 as an interesting postwar commentary, with Sinatra’s Danny Ocean and his buddies, all veterans of World War II, trying to find some meaning in their otherwise unexciting suburban lives. Or you could just listen to the movie’s director, two-time Oscar-winner Lewis Milestone (All Quiet on the Western Front), who abhorred working with Sinatra. “When Frank wasn’t actually acting himself, he would say, ‘Get him to do this,’ or ‘Make sure he does that,’” Milestone said. “Ask me which was my least favorite film that I ever made and it has to be Ocean’s 11.” 

The Manchurian Candidate (1962)

A tense psychological thriller about brainwashed American soldiers captured by the enemy during the Korean War, The Manchurian Candidate brought political assassination to the mainstream just a year before John F. Kennedy’s murder in Dallas. Sinatra plays one of the soldiers, Marco, who doesn’t remember much of the war but whose memory will be jogged once he falls for a mysterious beauty, Rosie (Janet Leigh), eventually coming to realize that he has to stop his old cohort Shaw (Laurence Harvey) from killing while under mind control. 

Director John Frankenheimer wasn’t sure about casting Sinatra, though, hearing he was a nightmare on set. He was pleasantly surprised to be wrong. As Frankenheimer’s widow Evans later recalled, Sinatra told her husband, “I’m an entertainer, John, I’m not an actor. I’m used to giving my all on the first go-round, I’m not used to repeating a scene. I certainly don’t repeat each evening [as a singer] — if I make a mistake or don’t like it, I don’t suddenly say, ‘Oops, I’m going to sing that again.’ … I find that all my takes seem to be best on the first take.”

That instinctive attitude was ideal for The Manchurian Candidate, which despite its lofty reputation is actually an expertly grubby paranoid thriller. Sinatra’s broken, desperate Marco is one of his best creations, and the movie feels appropriately sweaty and urgent, as if it’s all a bad dream the characters are trying to awaken from.

Tony Rome (1967)

As a recording artist, Sinatra was still riding high in the late 1960s, enjoying huge hits with “Strangers in the Night,” “That’s Life,” “Summer Wind” and “Somethin’ Stupid.” That wasn’t as true for his film career: Now in his early 50s, his swinging-playboy routine wasn’t nearly as charming as it used to be. Wisely, the Chairman made a course correction, focusing on roles as grizzled detectives and private investigators, guys who’d seen the worst of humanity.

He teamed up with journeyman director Gordon Douglas for this solid noir, in which he’s Tony Rome, a former cop who now lives on a boat in Miami. Soon, he’s involved in a mystery that features murder and a missing diamond pin. Clearly, Sinatra is channeling Humphrey Bogart in his performance of this burned-out P.I., but you can also see a hint of the man’s-man lone-wolf posturing that would also be central to the appeal of Clint Eastwood’s Dirty Harry.

As such, Tony Rome is fairly dated. (As Slant’s Chuck Bowen notes, the film, and its sequel Lady in Cement, hit theaters “when the counterculture was gaining brief prominence in pop culture, which is to say that Sinatra’s unconquerable heteronormative white he-man shtick … might have been wearing thin.”) But even so, there’s something poignant about an aging, tough-guy gumshoe who doesn’t realize the world has passed him by. He doesn’t even end up with the girl.  

43rd Annual Academy Awards (1971)

In the second installment of his two-volume Sinatra biography, Sinatra: The Chairman, James Kaplan sets the mood for the 1971 Oscars, where the actor would receive the Jean Hersholt Humanitarian Award: “Hollywood, which Frank had steadily dishonored over the past decade, seemed to have grown instantly wishful at the thought of his departure. On Academy Awards night … Gregory Peck presented Sinatra with his third Oscar, this time for his charitable works but also as a kind of unofficial farewell.”

But Sinatra was gracious in the moment, telling the crowd at the Dorothy Chandler Pavilion, “I’ve been thinking about why you have to get famous to get an award for helping other people … If your name is John Doe, and you work night and day doing things for your helpless neighbors, what you get for your effort is tired.” He invited all those who worked in anonymity doing good for others “to take your share of this Jean Hersholt Humanitarian Award,” later adding, “Your way of earning it was harder than my way. … I mean, in show business, they pay quite well.”

It was a humble speech but also an odd one. As Kaplan points out, Sinatra opened his remarks by doing an imitation of the character Kingfish from the racist program Amos ‘n’ Andy, saying, “I’m what is know in the vernacular as a re-tired man now.” His appearance was quintessential Frank Sinatra: Sincere but also a little dunderheaded, his best intentions mixing with his worst impulses.

Sinatra rarely appeared in films afterward — and if he did, it was usually as himself. For the next two decades, he focused his attention on music, which was always his first love. But unlike so many musicians who try their hand at Hollywood — Elvis, Prince, Madonna — he can lay claim to an acting career that was admirably substantial and worth revisiting.