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.

Crosby has been married to Joan Crane Foley since 1966. They have two children. He has been a Freemason since 1956, having served as Master of at least one lodge and participated in many charitable activities. As of September 2005, he was a member of Ionic Composite Lodge #520 in Los Angeles, California.

In the late 1970s and early 1980s, Crosby became a commercial pitchman for Anheuser-Busch Natural Light beer. During this time, he also appeared as a Celebrity guest on a number of game shows, including Celebrity Bowling, Liar's Club, Tattletales and Hollywood Squares. From 1983 until the program's disassociation with Jerry Lewis, Crosby co-hosted and contributed to the annual Jerry Lewis MDA Labor Day Telethon. He has a star on the Hollywood Walk of Fame at 6560 Hollywood Boulevard.

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. From 1978-81, he hosted a nationally syndicated series, The Comedy Shop, in which a mix of up-and-coming stand-up comics and vaudeville legends presented their material.