Crosby went solo as standup comedian, adopting a friendly, blue collar, guy-next-door persona in the 1950s. Crosby refined his standup monologues by interpolating malapropisms. He first appeared on The Tonight Show Starring Johnny Carson in December 1964. In the fall of 1968, he co-starred on The Beautiful Phyllis Diller Show, an NBC twelve week series.
In 1974, he co-hosted a Canadian variety television series, Everything Goes. From 1974-84 he was on over half a dozen Dean Martin Celebrity Roasts including George Burns and two separate roasts of Redd Foxx.