Metro Goldwyn Mayer
"On the Town" (1949)
Sinatra's recording and film career starting to go into a lull in 1948. But then it saw an upturn when he teamed with his pal Kelly in two musicals in '49, the enjoyable "Take Me Out to the Ballgame" and this classic, which marked the directing debut of Kelly and Stanley Donen. Based on the seminal Broadway musical by Leonard Bernstein, Betty Comden and Adolph Green, "On the Town" revolves around three sailors (Sinatra, Kelly and Jules Munchin) who find love while on a 24-hour leave in New York City. Sinatra plays the earnest Chip, who becomes the objected of the dogged affection of a taxi driver named Brunhilde (Betty Garrett). The two have a great musical number together: "Come Up to My Place."