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This Chicago native was born to be funny and started to use his talent in high school, creating a sketch group called Mary Wong. The group was so successful that they began to tour the States on various campuses. The attention was nothing new to Crouther, who was also working as a traveling stand-up comedian performing in clubs and colleges.
Moving to Los Angeles, Crouther started writing for comedians, as well as a number of television pilots and shows such as The Gregory Hines Show. He also landed a regular gig writing for the show, Comic Justice, for two years. In 1997 he started to write for The Chris Rock Show. It proved to be a fruitful experience, as Crouther earned an Emmy and a CableAce Award for his work. His working relationship with Chris Rock led him to more projects, including writing for Saturday Night Live; a couple of comedy albums including Roll with the New; and a feature film screenplay, Down To Earth (2001).
During the '90s, he landed a number of minor roles in feature films. By the new millennium he took on his first starring role in the film Pootie Tang (2001).