Every Gene Kelly & Frank Sinatra Movie, Ranked

Here’s every movie that Gene Kelley and Frank Sinatra starred in together, ranked from worst to best. The Golden Age of Hollywood spawned many an iconic onscreen pairing. Fred Astaire and Ginger Rogers dazzled with their dance routines in Top Hat and Swing Time, Bob Hope and Bing Crosby made audiences laugh with their series of Road To… movies, and husband-and-wife duo Humphrey Bogart and Lauren Bacall smoldered both on and off camera in noirs like The Big Sleep and Key Largo.

Gene Kelly and Frank Sinatra were another iconic duo brought together during the Golden Age of Hollywood, although they only starred in three films together. The pair met when they were signed with MGM and cast in the 1945 musical comedy Anchors Aweigh, which kickstarted a fruitful (yet short-lived) partnership and a lifelong friendship. Onscreen their strengths complemented each other’s weaknesses perfectly, with Gene Kelly’s extraordinary dancing skills making up for the somewhat rhythmically challenged Sinatra’s lack of moves, while Sinatra’s dulcet crooning making up for the notes Kelly couldn’t quite hit.

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The pair were set to collaborate a fourth time with the 1964 musical comedy Robin And The 7 Hoods which Frank Sinatra produced and starred in alongside Rat Pack pals Dean Martin and Sammy David Jr. Kelly was set to co-produce the movie but reportedly left the production due to disagreements with Sinatra, albeit on amicable terms. Nevertheless, the dynamic duo remained friends and gave the world three musical movies to enjoy – but which Gene Kelly and Frank Sinatra film ranks as the best?

Take Me Out To The Ball Game

Released in early 1949, Take Me Out To The Ball Game was Gene Kelly and Frank Sinatra’s second collaboration. The turn-of-the-century set movie stars Kelly and Sinatra as a pair of baseball players who moonlight as vaudeville performers during the off-season (which explains why they’re prone to bursting into song) and find their dynamic thrown off-kilter by the arrival of their new team owner, who turns out to be a woman (played by Esther Williams) who they both fall in love with. While it’s an enjoyable musical comedy, Take Me Out To The Ball Game is Kelly and Sinatra’s weakest film thanks to a flimsy plot and not-so-great pacing.

Anchors Aweigh

Directed by George Sidney in 1945, Anchors Aweigh was the film that brought Gene Kelly and Frank Sinatra together and cast them as a pair of U.S. Navy sailors on shore leave in Hollywood. Kelly plays cocky ladies’ man Joe Brady while Sinatra plays against type as shy choir-boy-turned-sailor Clarence Doolittle and – like Take Me Out To The Ball Game – the pair end up falling for the same woman (aspiring actress Susan Abbott, played by Kathryn Grayson). Anchors Aweigh boasts an ahead-of-its-time musical number that mixes animation and live-action in which Kelly dances seamlessly alongside a cartoon Jerry (of Tom and Jerry fame), and its two stars have great chemistry but it’s not their best movie.

On The Town

Filmed shortly after production on musical Take Me Out To The Ball Game wrapped, On The Town was Gene Kelly and Frank Sinatra’s third and final film together. Its premise is admittedly similar to Anchors Aweigh, with Kelly and Sinatra playing a pair of sailors on shore leave in New York, but at least its stars aren’t pitted against each other as love rivals this time. Based on Leonard Bernstein’s Broadway musical, On The Town won an Oscar for Best Musical Score and has since been recognized by the American Film Institute as one of the great movie musicals of all time. It’s a charming comedy romp and without a doubt Gene Kelly and Frank Sinatra’s best collaboration.

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