Wilson kept performing and acting until the 1990s, though at a reduced schedule, up until his death from cancer in 1998. He hosted a short-lived revival of People Are Funny in 1984, and he had the lead role in the 1985–1986 sitcom Charlie & Co.
In the late 1950s and early 1960s, Wilson toured regularly through nightclubs with a black clientele in the so-called "Chitlin' Circuit". During the 1960s, Wilson became a regular at the Apollo Theater in Harlem. An unexpected break came in 1965, when comedian Redd Foxx was a guest on The Tonight Show and host Johnny Carson asked him who the funniest comedian at the time was; Foxx answered, "Flip Wilson". Carson then booked Wilson to appear on The Tonight Show and Wilson became a favorite guest on that show as well as on The Ed Sullivan Show. Wilson later singled out Sullivan as providing his biggest career boost. Wilson also made guest appearances on numerous TV comedies and variety shows, such as Here's Lucy (in which he played the role of "Prissy" in a spoof of Gone with the Wind with Lucille Ball as Scarlett), Laugh-In, and The Dean Martin Show, among others.
Wilson's warm and ebullient personality was infectious. Richard Pryor told Wilson, "You're the only performer that I've ever seen who goes on the stage and the audience hopes that you like them."
A routine titled "Columbus", from the 1967 album Cowboys and Colored People, brought Wilson to Hollywood industry attention. In this bit, Wilson retells the story of Christopher Columbus from an anachronistic urbanized viewpoint in which Columbus convinces the Spanish monarchs to fund his voyage by noting that discovering America means that he can also discover Ray Charles. Hearing this, Queen "Isabel Johnson", whose voice is an early version of Wilson's eventual "Geraldine" character, says that "Chris" can have "all the money you want, honey – You go find Ray Charles!" When Columbus departs from the dock, an inebriated Isabella is there, testifying to one and all that "Chris gonna find Ray Charles!"
In 1970, Wilson won a Grammy Award for his comedy album The Devil Made Me Buy This Dress. He was also a regular cast member on Rowan & Martin's Laugh-In. DePatie-Freleng Enterprises featured Wilson in two animated TV specials, Clerow Wilson and the Miracle of P.S. 14 and Clerow Wilson's Great Escape.
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