Higher and Higher (1944)–Starring Frank Sinatra in First Role

In this comedy with songs, Leon Errol plays a rich man who relies on his servants to get his money back, when his fortune goes down.

Directed by Tim Whelan, the film marks Sinatra’s screen debut in a cast that includes Jack Haley, Michele Morgan, Victor Borge, Mary Wickes, and Mel Thorme.

Oscar Nominations: 2

Song: I Couldn’t Sleep a Wink Last Night, music by Jimmy McHugh, lyrics by Harold Adamson

Scoring of Musical: C. Bakaleinikoff.

Oscar Awards: None

 

Oscar Context:

The Song winner was Swinging on a Star, by James Van Heusen and Johnny Burke, from Going My Way.

The Scoring Oscar went to Carmen Dragon and Morris Slotoff for Cover Girl.