Benchley's roles primarily came as a freelance actor, as his Paramount shorts contract didn't pay as well as feature films. Benchley was cast in minor roles for various romantic comedies, some shoots going better than others. He appeared in prominent roles with Fred Astaire in "You'll Never Get Rich" (1941) and "The Sky's the Limit" (1943). Paramount did not renew his contract in 1943, and Benchley signed back with MGM with an exclusive contract. The situation was not positive for Benchley, as the studio "mishandled" him and kept Benchley too busy to complete his own work. His contract concluded with only four short films completed and no chance of signing another contract. Following the printing of two books of his old "New Yorker" columns, Benchley gave up writing for good in 1943, signing one more contract with Paramount in December of that year.