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Shawn Wayans graduated from high school in 1989, and in 1991 he joined several of his siblings in the cast of In Living Color, the highly acclaimed sketch-comedy show, also written and directed by Keenen Ivory Wayans. The show established the Wayans clan as a force to be reckoned with in Hollywood while also helping launch the careers of unrelated future stars like Jim Carrey and Jamie Foxx. Shawn Wayans left the show in 1993, but three years later, he again teamed up with brothers Keenen and Marlon to makeDon't Be a Menace to South Central While Drinking Your Juice in the Hood, a spoof of earnest coming-of-age-in-the-hood flicks like Boyz n the Hood.
Shawn Wayans gained wider popularity when he and brother Marlon costarred in the largely autobiographical sitcom The Wayans Bros., which aired on the WB network from 1995 to 1999. The show helped to establish both Shawn and Marlon among the most prominent members of their illustrious family. In 2000, Wayans co-wrote and also acted in his most popular film to date, the blockbuster horror spoof Scary Movie. The film, which cost only $19 million to make, raked in an astounding $157 million at the box office, making it the highest-grossing film ever directed by an African-American (Keenen Ivory Wayans). Shawn Wayans also co-wrote and appeared in the film's several sequels: Scary Movie 2 (2001), Scary Movie 3(2003) and Scary Movie 4 (2006). Apart from the Scary Movie series, Shawn Wayans and his brother Marlon have also starred in the popular spoof filmsWhite Chicks (2004), Little Man (2006) and Dance Flick (2009).