Lucky Boy is a 1929 American sound part-talkie musical comedy-drama film directed by Norman Taurog and Charles C. Wilson, most notable for starring George Jessel in his first known surviving feature picture.

The film was originally developed with the title The Schlemiel based on a story by Viola Brothers Shore.

[11] It was initially filmed without sound by director Norman Taurog under the working title of The Ghetto in April 1928,[12] reportedly in a "record time" of twelve days.

[3] The film also featured a score by Hugo Riesenfeld;[16] "You're My Real Sweetheart" and "In My Bouquet of Memories" by Sam M. Lewis, Joe Young, and William Axt; "Keep Sweeping the Cobwebs Off the Moon" by Sam M. Lewis, Joe Young, and Oscar Levant; and "My Blackbirds are Bluebirds Now" by Irving Caesar and Cliff Friend.

[19] As well as becoming Jessel's signature number, the song was re-recorded several times, including an instrumental version by Tab Smith (1952), Frankie Valli's debut 1953 single (which also featured in the 2005 jukebox musical Jersey Boys and its 2014 film adaptation), and the titular song from the Sonny Stitt album, My Mother's Eyes (1963).