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The show ran for a total of 220 episodes until the show's cancellation in 2006.
In 1998, the New York Friars' Club made Carey the newest inductee of the group's Comedy Central Roast.
After their stint on Someone Like Me, Carey and Helford developed and produced the storyline for The Drew Carey Show.
The sitcom revolved around a fictionalized version of Carey, as he took on the stresses of life and work with his group of childhood friends. In his autobiography, Carey revealed his frustration with having to deal with censors and being unable to employ the off-color humor common in his stand-up routines.
Beginning in 2007, Carey began hosting game shows, beginning with his April selection as host of the CBS game show pilot Power of 10.
The show ran from August 7, 2007, to January 23, 2008, and aired twice weekly during the late summer and early fall.
In the April Fools' Day 2013 episode, Carey and announcer George Gray switched places with the models, letting the two men be the models for the episode.
Carey was one of the founders of the Improv All-Stars, a group of eleven actors who perform in unscripted skits.
The group joined Carey in all three of his improv shows, Whose Line Is It Anyway?
Carey began appearing in commercials for restaurants in the late 1990s in Canada with The Great Root Bear, but his two-year contract with A&W Food Services of Canada was cut short in November 1998 after an episode of The Drew Carey Show featured Mc Donald's.
As a result of his dismissal, Carey sued A&W for compensation.
The program had a total of 233 episodes over its nine-year run, and Carey was one of four actors to appear in every episode.