Performed at the Improv in New York during his summer vacation from college
Moved to New York after leaving college and worked the stand-up comedy club circuit
Moved to Los Angeles and eventually worked at the Los Angeles Improv and the Comedy Store
Signed a development deal with NBC
Made TV acting debut in the NBC sitcom (pilot), "Irene"
First film appearance, Bob Fosse's "Star 80"
Was a series regular on "For Love and Honor" (NBC)
First feature as co-screenwriter (with director Robert Townsend), "Hollywood Shuffle"; also acted
Debut as a producer (also co-writer), "Eddie Murphy Raw"
TV debut as producer, "Robert Townsend's Partners in Crime" (HBO)
Feature directing debut, "I'm Gonna Git You Sucka"; also wrote and acted
Co-created (with brother Damon) the sketch comedy series, "In Living Color" (FOX); also wrote, produced and co-starred with several siblings
Signed exclusive movie and TV deal with 20th Century-Fox
Ended his film and TV deal with 20th Century Fox to protest censorship of "In Living Color" and to protest Fox's decision to rerun first season episodes without his consultation; left the show at the end of the third season, but remained the executive producer through the fourth season
With brothers Shawn and Marlon created, "Thugaboo," (Nickelodeon) a series of animated children's shows that follows the misadventures of nine kids growing up in the inner city
Directed brothers Marlon and Shawn in the comedy, "The Little Man"; also co-wrote
Wrote, directed and starred in the action film, "A Low Down Dirty Shame"
Produced the film, "Don't Be a Menace to South Central While Drinking Your Juice in the Hood," starring his brothers Marlon and Shawn
Co-starred with Steven Seagal in the action film, "The Glimmer Man"
Hosted the syndicated late night talk-show, "The Keenen Ivory Wayans Show"
Directed the horror parody, "Scary Movie," starring his brothers Shawn and Marlon
Once again directed brothers in the sequel, "Scary Movie 2"
Had a recurring role on the ABC sitcom, "My Wife and Kids"; created by and starring brother Damon
Co-wrote (with brothers Marlon and Shawn) the comedy, "White Chicks"; also produced and directed
Directed his brothers Marlon and Shawn in the direct-to-video, "Little Man"
Produced and co-wrote the comedy spoof, "Dance Flick"; directed by nephew Damien Dante Wayans