10 Best Frank Sinatra Movies, According to Rotten Tomatoes

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10 Best Frank Sinatra Movies, According to Rotten Tomatoes

A true entertainer that managed to do it all during his career, from music to television and film. Known for his blue eyes and beautiful voice, Frank Sinatra was one of the biggest hits of his generation. His prowess as an entertainer was visible as he could always galvanize an audience.


Frank Sinatra’s career ebbed and flowed as he would experience many dark days. From this he was able to take his experiences and put them into performances on camera. Sinatra was a sensitive man that had a temper and was not always the most moral figure. Always committed to a vision, he was loyal and unwavering in what he wanted. The films scored by Rotten Tomatoes are a diverse set of films from Sinatra’s time making movies, though some of his most iconic roles may not be apart, these are films have been scored for good reason.

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10 ‘High Society’ (1956)

Image via MGM

Rotten Tomatoes Score:83%

It took not even two decades before a remake of the classic film The Philadelphia Story was re-made into a musical that stands up nicely to the original about a socialite (Grace Kelly) that is going to remarry. Her ex-husband (Bing Crosby), still in love with her, hires a journalist (Sinatra) to help convince her that she still loves him.

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Sinatra may not deliver the Academy Award-winning performance like James Stewart, but he brings his own new qualities to the character. Sinatra’s Mike Connor is a blue collar worker bluffing his way through the wealthy world around him. Throughout his career Sinatra had always felt like an outsider to the industry, a chip on his shoulder that he carried around often.

9 ‘From Here to Eternity’ (1953)

frank-sinatra-from-here-to-eternity - montgomery clift
Image via Columbia Pictures 

Rotten Tomatoes Score:88%

The film takes place at an army barracks in Hawaii during the days preceding the attacks on Pearl Harbor. Sinatra plays Maggio, the best friend of Prewitt (Montgomery Clift), a private who refuses to box in the unit’s team.

At the time Frank was auditioning for the role of Maggio his career was in a down spell. He needed this part to bring himself back in the spotlight. That desperation goes hand in hand with the character. Sinatra knew what it was like to be an underdog and when it came to Maggio, he was him, so much so that Sinatra was willing to pay for his audition tape.

8 ‘Young at Heart’(1954)

day-sinatra-at-piano_young-at-heart- Doris-Day
Image via Warner Bros 

Rotten Tomatoes Score:90%

The song Young at Heart was sung by the character Barney Sloan. Barney is a music arranger that comes to musical families’ households with a cynical outlook on life that proves to be too much for the sisters he has to help.

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Frank is perfect in this role as his cynical views are the highlight of the character. Part of Frank’s allure was the emotion he put into performances; he was able to capture ineffable feelings into the songs he sang.

7 ‘Von Ryan’s Express’ (1965)

Frank Sinatra- Von Ryan's Express
Image via 20th Century Fox 

Rotten Tomatoes Score:90%

In the midst of World War II, an American POW helps a group of Italian POW’s escape from the camp. Sinatra plays Joseph Ryan, a colonel that gets shot down while flying over Italy.

Sinatra was emotionally attuned to the material he worked on. Von Ryan’s Express had a happy ending in the book that Sinatra decided to change into a big traumatic final scene. Giving conviction to everything he did brought his own sense of style to the films.

6 ‘Guys and Dolls’ (1955)

Frank Sinatra- Guys and Dolls
image via MGM

Rotten Tomatoes Score: 91%

From the Broadway musical, Frank plays a gambler who is challenged to take an apathetic missionary to Havana. Though the hidden motives threaten the relationship as they come to care for each other.

RELATED: 10 Most Memorable Musicals from Hollywood’s Golden Age

Typically, Sinatra plays the singer and Brando the gangster, but roles were reversed as Sinatra took on the part of Nathan Detroit. Desperate for the role as he was still coming out of his latent period, Sinatra reverted close to his character of Clarence Doolittle in Anchors Aweigh, to be timid and awkward.

5 ‘On the Town’ (1949)

on-the-town- Three-sailors-on-leave
Image via Loew’s,inc 

Rotten Tomatoes Score:93%

When three sailors get to New York City on a twenty-four-hour leave, there isn’t much to do but go around the city in search of love. The film was deemed a success thanks to the direction of Gene Kelly and Stanley Donen.

Worn by the work of wearing sailor outfits, this would be the final film pairing Sinatra and Kelly. Sinatra’s yearning to play dramatic roles was intensifying as the film left behind an era of Sinatra that is looked on with fondness. The tactile ability to keep up with Kelly shows how talented Sinatra was in general.

4 ‘Take Me Out to the Ball Game’ (1949)

take-me-out-to-the-ball-game-Gene-Kelly-and-Frank-Sinatra
Image via Loew’s, Inc 

Rotten Tomatoes Score:95%

Two baseball players (Sinatra and Gene Kelly) return from their Summer on Vaudeville to their team that has a new owner they butt heads with. Meanwhile, a gambling tycoon who will do anything to win his bets.

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Sinatra was put into the role to steady his career after his last movie Knock At My Door failed. Take Me Out to the Ball Game was a safe choice for MGM to put Sinatra back with Kelly. Though the film is looked at as a very jovial time, Sinatra was a menace on set to the revered director Busby Berkeley. Behind the song and dances, Sinatra would often show up late to set and botch dance numbers wasting hours of time.

3 ‘The Manchurian Candidate’ (1962)

Frank Sinatra- The Manchurian Candidate
Image via United Artists 

Rotten Tomatoes Score:97%

As a POW following the Korean War, Sinatra is a brainwashed assassin who will do anything for the leader of an International Communist conspiracy. He is returned home only with nightmares to help him uncover a disturbing plot.

Sinatra loved the script for The Manchurian Candidate as it dealt with politics at a hard time in US history with McCarthyism and the Cold War being relevant issues. With the film being independent Sinatra was able to take much control over the film, though working with a strong-willed John Frankenheimer brought out the best performance in him as all his insecurities and neurosis were put into a character that is paranoid.

2 ‘Suddenly’ (1954)

Frank Sinatra-Suddenly
Image via United Artists 

Rotten Tomatoes Score:100%

When the President of the United States comes to the small town of Suddenly, an assassin with two other gang members holds a family hostage. Using the house as a vantage point they plan to kill the President of the United States.

Chillingly prophetic, Sinatra doesn’t come into the film until twenty minutes in, from there he murders a Secret Service agent and attention is on him the rest of the way. A role that the public had never seen him in before was shocking as the blue-eyed boy was no longer just a glam piece. The film was mainly shot using Sinatra’s scarred side of his face in tight frames and close-ups that made the anxiety of the film palpable.

1 ‘The Detective’ (1968)

Frank Sinatra- The Detective
image via 20th Century Fox 

Rotten Tomatoes Score: 100%

A neo-noir has Sinatra playing Joe Leland, a detective covering a murder in New York City. Leland comes to discover the case may have more to it as he discovers a cover-up.

One of his last great roles, Sinatra takes the heartache from his own life as his character deals with a broken marriage. His time with Mia Farrow was coming to an end and his previous relationships had given way to a dedicated performance. His tough and grim demeanor fit to the deteriorating city politics around him.

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