When thinking of the great Frank Sinatra, his prolific music career most likely comes to mind. His smooth singing voice and timeless songs are still listened to today, with over 12.3 million monthly listeners on Spotify. However, the crooner and New Jersey native had a lengthy career in film as well. Of course, he was perfectly suited for musicals, and he did star in his fair share of them. His film career was more diverse than that, though. Sinatra starred in many different genres of movies, from war films to film noir.
It comes as no surprise that musicals were his strong suit, but Sinatra displayed the power of his acting chops in dozens of movies throughout his career that proved he was more than just his incredible music career. While not every movie he made ended up being memorable, he always gave his best when the cameras were rolling. Whether he was the leading man or part of the ensemble, he brought his best game each time. In fact, he consistently made the Top Ten Money Making Stars Poll from 1956-1960 and then again in 1962. Without further ado, here are 13 quintessential Frank Sinatra movies.
Updated May 24, 2024: If you love Frank Sinatra, you're in luck. This article has been updated by Rachel Johnson with even more Sinatra movies you need to watch.
13 The Joker Is Wild (1957)
During the Prohibition era in the United States, speakeasy crooner Joe E. Lewis' (Sinatra) career and nearly his life are cut short when his throat is slashed as payback for leaving his job in the Chicago mob. Left with alcoholism, Joe's piano player helps the former singer turn himself into a successful stand-up comedian.
Fiction Mirrors Reality in The Joker Is Wild
The Joker Is Wild is an interesting role for Sinatra as his character begins the movie with the same career that Sinatra himself became known for. It then follows his character as he becomes a stand-up comedian, and while Sinatra never had a career in comedy, he certainly dabbled in comedic movies. This movie itself is a dark comedy that explores the life of stage performers and what goes on behind the scenes that audiences rarely catch a glimpse of.
12 Can-Can (1960)
Set in 1896 Paris, the lively musical Can-Can features Shirley MacLaine as nightclub owner Simone Pistache, whose evening performances of the risque titular dance attract the unwanted attention of the uptight Judge Philippe Forrestier, a man on a self-righteous mission to punish the daring proprietress and shut the establishment down. Sinatra appears as Simone's shady lawyer boyfriend François Durnais, who shockingly finds competition from the stuffy court official and must attempt to win back his lady love.
Can-Can Is a Rip-Roaring Good Time
In the toe-tapping picture, Sinatra performed memorable musical numbers like "It's All Right with Me" and "Let's Do It, Let's Fall in Love," ultimately helping the film win the Grammy Award for Best Motion Picture Soundtrack. Can-Can was also nominated for two Oscars and a Golden Globe and highlighted Sinatra's overwhelming star power at the time, as the performer was paid $200,000 and earned 25% of its overall profits. Despite his character being crooked and a commitment-phobe, Sinatra brought his signature charisma to the role.
11 Some Came Running (1958)
Some Came Running follows a heavy-drinking writer named Dave Hirsh (Sinatra) when he returns home as an army veteran. His brother wants him to settle down, so he introduces him to an English teacher, but moody Dave resents his brother for this and instead spends his days hanging out with a professional gambler who loves to party. Torn between the English teacher and Ginny Moorehead, a woman who already loves him, Dave grows angry with life after returning to his hometown.
Some Came Running Is a Star-Studded Romantic Affair
Alongside Sinatra, this movie has an all-star cast including Shirley MacLaine and Dean Martin. With a romance subplot, the movie details the harsh realities that people face when they return home from war and the troubles they encounter with assimilating back into civilian life. A stark departure from musicals or comedies, Sinatra shines here as a man trying to adjust to a normal life once again.
10 Anchors Aweigh (1945)
Sinatra partnered up with dancer extraordinaire Gene Kelly for the musical comedy Anchors Aweigh, in which the talented duo portray Navy sailors Clarence and Joe as they find themselves on leave in glamorous Hollywood, where they both become captivated by sultry aspiring singer Susan after safely returning her runaway nephew. Though the pals wanted to have a relaxing break, they make it their mission to help Susan break into show business, with comical hijinks ensuing along the way.
Anchors Aweigh Is an Oscar-Nominated Vocal Venture
Unsurprisingly, Sinatra and Kelly proved to be cinema gold when the musical hit theaters, with the pair serving up playful performances that allowed the actors to let loose. The film was a massive box office success and Sinatra's delightful rendition of the romantic ballad "I Fall in Love Too Easily" earned the crooner and moving tune an Academy Award nomination for Best Original Song.
Why It's Taken More Than 20 Years for Scorsese to Make His Sinatra Movie
One of the greatest filmmakers of all time has had a harder time than you'd think cracking Frank Sinatra.9 The Man with the Golden Arm (1955)
Skilled card dealer Frankie Machine (Sinatra) must combat his drug addiction and face his true self after a six-month stint in prison after taking the fall as the dealer for his gambling boss, who got him addicted to drugs in the first place. With his former drug dealer intent on getting him hooked again, trying to stay clean, getting out of the card dealing business, and choosing between his wife and the woman he actually loves, Frankie has a long journey ahead.
Sinatra Showcases His Range in The Man with the Golden Arm
Another role in a film drastically different from what he was known for, Sinatra was able to thrive in an environment much different than what he was used to in The Man with the Golden Arm. Starring alongside Kim Novak, Sinatra was once again able to show audiences that he could do much more than just sing. He was a talented actor with the ability to carry a movie.
8 Pal Joey (1957)
Touting a star-studded ensemble cast of Hollywood legends led by Sinatra, Rita Hayworth, and Kim Novak, the musical comedy Pal Joey is based on the play of the same name and centers on the smooth-talking womanizer Joey Evans, a San Francisco based singer who becomes torn between his feelings for his former flame and ex-burlesque dancer Vera (Hayworth) and the sweet-yet-naive chorus girl Linda English (Novak). Joey must decide what path he wants in life and which romantic prospect will bring out the best in him.
Hollywood Greats Dominate the Screen in Pal Joey
Kirk Douglas was initially attached to star in the lead role, but the studio felt Sinatra was the perfect choice to play the notorious lothario, and his sizzling on-screen chemistry with both Hayworth and Novak further proved this fact. Not only was Pal Joey a massive hit with moviegoers, but it also nabbed Sinatra another Golden Globe Award. Despite not receiving top-billing (Hayworth was given that distinction), a gracious Sinatra cheekily declared that being billed between the two actresses was "a sandwich I don't mind being stuck in the middle of."
7 The Manchurian Candidate (1962)
Based on the novel of the same name written by Richard Condon, The Manchurian Candidate is set during the end of the Korean War where a platoon of U.S. soldiers is captured by communists. When the platoon returns home after the war ends, Sergeant Raymond Shaw (Laurence Harvey) is labeled a hero by the platoon. However, their commander, Captain Bennett Marco (Sinatra), is plagued by nightmares and ends up racing to uncover a horrible plot.
A Truly Compelling Performance
This thrilling book-to-screen adaptation was another starring vehicle for Sinatra where he was able to showcase his ability to act in a variety of movie genres. He was able to capture the troubled mind of a war veteran and former captain struggling with a recurring nightmare about one of his soldiers and what that means for him and the rest of his troop.
6 On the Town (1949)
When a trio of sailors has a 24-hour pass in New York, they let loose and turn the Big Apple upside down. Between the three of them, one falls in love, one gets highjacked by a cab driver, and one becomes the object of interest of an anthropologist.
Sinatra Shines in His Element in On the Town
This musical-comedy follows Sinatra, Gene Kelly, and Jules Munshin as they sing and dance their way through the streets of New York during their day full of shenanigans before they get sent back to sea. On the Town is a screen adaptation of the Broadway musical of the same name that was originally on stage in 1944, so Sinatra was perfectly cast as one of the three sailors.
Why Are Modern Movies Obsessed with Old Hollywood?
In addition to superheroes and intergalactic stories, Hollywood movies today often look to the past for inspiration. Here's why.5 High Society (1956)
In addition to Sinatra, High Society also stars A-listers of the time, Grace Kelly and Bing Crosby. The film is a remake of the 1940 rom-com The Philadelphia Story and follows childhood friends Tracy Lord (Kelly) and C.K. Dexter Haven (Crosby) who got married and then quickly divorced. Tracy is about to marry a social-climbing businessman, despite C.K. still loving her. Throughout all of this, Tracy's family is blackmailed by a magazine if they are not allowed to cover the big wedding. The undercover reporter that is sent by the magazine, Mike Conner (Sinatra), also falls for Tracy, and she must choose between the three men.
High Society Is an Undisputed Rom-Com Classic
Any team-up between Sinatra and Crosby is bound to be entertaining, and with Grace Kelly added into the mix, there is no shortage of entertainment in this film. It's a rom-com musical featuring a love triangle portrayed by three of the biggest stars of their time, and really, three of the biggest stars to ever enter the film industry. Plus, Louis Armstrong has an appearance as himself as well.
4 Take Me Out to the Ball Game (1949)
Once again, Sinatra reunited with Gene Kelly for this summer baseball film, Take Me Out to the Ball Game, which followed to baseball players that were into vaudeville during the off-season. When they return for the start of the season, however, they discover that their team has been sold and that the new owner will be actively participating in the management of the team. They are even more shocked to discover that the new owner is a woman named K.C. Higgins (Esther Williams).
Sinatra Hones His On-Screen Skills in This Baseball Movie
This time around, it is evident that Sinatra grew more comfortable with his dancing skills around Kelly. When they worked together previously, it was clear that Sinatra was watching Kelly for guidance and was perhaps a bit insecure in his ability to dance around someone such as Kelly. In this movie, he was a multi-talented, bona fide star.
3 Ocean's 11 (1960)
The original Ocean's 11 film follows Danny Ocean (Sinatra) as he gathers a group of his World War II buddies to pull off the ultimate heist in Las Vegas. Together, the eleven army friends devise an elaborate plan to rob five Vegas casinos in just one night.
The Rat Pack Dazzles Audiences in Ocean's 11
While the 2001 remake also had an incredible cast including George Clooney, Brad Pitt, and Matt Damon, the 1960 original paved the way for the modern remake to be made. It featured talented actors in addition to Sinatra, and while Sinatra himself didn't sing, Dean Martin and Sammy Davis Jr. both had songs included in the movie. It was another movie in which Sinatra was able to showcase his ability to lead an ensemble cast.
2 From Here to Eternity (1953)
At a U.S. Army base in Hawaii during 1941, a private is cruelly punished for not boxing on his unit's team, while his captain's wife and his second in command are falling love in the days before the attack on Pearl Harbor.
From Here to Eternity came out during a time in Sinatra's life where everything was falling apart around him.
Sinatra's Much-Needed Saving Grace in From Here to Eternity
Sinatra had an affair with Ava Gardner, a vocal hemorrhage in 1950 that had severely damaged his vocal cords that caused his record label to drop him, and a reputation as box office poison after a string of flops. The career Sinatra had built for himself was crumbling around him quickly. When the role of Angelo Maggio, the scrappy anti-hero of the film, opened up after Eli Wallach was unavailable, Sinatra assumed the role. It proved to be more than worth it for him, as he went on to win Best Actor in a Supporting Role at the 1954 Academy Awards and kickstarted his comeback journey.
1 Guys and Dolls (1955)
Guys and Dolls
- Release Date
- December 23, 1955
- Director
- Joseph L. Mankiewicz
- Runtime
- 150
A notorious gambler in New York named Nathan Detroit (Sinatra) needs $1,000 to host his next big craps game, so he bets Sky Masterson (Marlon Brando) that he cannot take missionary Sarah Brown (Jean Simmons) out on a date. Sky negotiates a date with Sara in exchange for bringing people into her missionary. During this bet, Nathan's longtime fiancé, Adelaide (Vivian Blaine), tells him that she wants him to go legit and marry her.
Sinatra & Brando Make Movie Magic
Guys and Dolls is one of the most famous musicals of all time, and its screen adaptation put two of the most famous stars of all time in the two leading men's roles. Marlon Brando is often considered one of the greatest actors of all time, and Sinatra is often referred to as one of the greatest singers of all time. The pair makes for a great on-screen duo, which in turn makes for an entertaining movie.
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