After the war, he launched himself onto the nightclub circuit with his new moniker, the "Orson" borrowed from reigning enfant terrible Orson Welles. His comedy act premiered at New York City's Blue Angel nightclub, and the momentum from his act launched him into the orbit of the legitimate theater. He made his Broadway debut on April 30, 1954 in Stalag 17 (1953) producer Richard Condon's only Broadway production as a playwright, "Men of Distinction", along with Robert Preston and Martin Ritt. The play flopped and ran only four appearances.
The following year was to prove kinder: he hosted a summer-replacement television series produced at the Blue Angel, and won a Theatre World Award for his work in the 1954 music revue "John Murray Anderson's Almanac", which co-starred Harry Belafonte, Polly Bergen, Hermione Gingold and Carleton Carpenter. It was a hit that ran for 229 performances. He followed this up with an even bigger hit, the leading role in "Will Success Spoil Rock Hunter". Next up was a success d'estime as the leading man in Herman Wouk's comic play "Nature's Way", which co-starred Bea Arthur, Sorrell Booke and Godfrey Cambridge. Though the play lasted but 67 performances, Orson Bean had established himself on the Broadway stage.