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 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).

[citation needed] Red Nichols (Kaye) is a small-town cornet player who moves to New York City in the 1920s and finds work in a band led by Wil Paradise (Crosby).

His first attempts to play a horn (he threw his own treasured instrument into the San Francisco Bay in despair when Dorothy was ill) are a miserable failure.