In 1929, saxophonist and original crooner Rudy Vallée segued into film, making his first feature film, The Vagabond Lover, for RKO Radio. His first films were made to cash in on his singing popularity. While his initial performances were rather wooden, his acting greatly improved in the late 1930s and 1940s, and by the time he began working with Preston Sturges in the 1940s, he had become a successful comedic supporting player. He appeared opposite Claudette Colbert in Sturges’s classic 1942 screwball comedy The Palm Beach Story and is so hilarious that he should have been nominated for Best Supporting Actor. Other films in which he appeared include The Bachelor and the Bobby-Soxer, I Remember Mama, and Unfaithfully Yours.

This article is part of a special year-long series of anecdotes, reflections and thoughts about the Academy Awards.