The Five Pennies is a 1959 American biographical music drama film in VistaVision and Technicolor starring Danny Kaye as jazz cornet player and bandleader Loring "Red" Nichols. Other cast members include Barbara Bel Geddes, Louis Armstrong, Harry Guardino, Bob Crosby, Bobby Troup, Susan Gordon, and Tuesday Weld. The film was directed by Melville Shavelson.

The film received four Oscar nominations: Best Musical Scoring (Leith Stevens), Best Original Song (Sylvia Fine—Danny Kaye's wife), Best Cinematography (Daniel L. Fapp), and Best Costumes (Edith Head).

The real Red Nichols recorded all of Kaye's cornet playing for the film soundtrack. The other musicians in Red's band were not asked to provide their musical contributions, and the sound of his band was supplied by session players.