The trail-blazing linchpin of a sprawling family dynasty of comic entertainers, it was multi-talented writer/director/producer Keenen Ivory Wayans (born June 8, 1958, in New York City) who led the familial pack and was the first to achieve national prominence when he successfully created, launched, wrote, hosted and starred in In Living Color (1990), a landmark 1990s black-oriented comedy sketch satire on Fox TV that beat the odds and transcended the then-narrow periphery of TV comedy to became a defiant movement of inclusion. It was a brilliant showcase for up and coming comics and not only ignited/advanced the careers of his own younger talented siblings (Damon Wayans, Kim Wayans, Shawn Wayans, Marlon Wayans), but the superstar film careers of Jim Carrey and Jamie Foxx.

The second of ten children of Howell Wayans, a grocery store manager, and Elvira Wayans, a social worker and singer, Keenan attended Seward Park High School, then majored in engineering at Alabama's Tuskegee University. He dropped out during his senior year when the comedy bug hit him full force. Heavily influenced by Richard Pryor, he found only lukewarm success on the New York stand-up stage, deciding later to relocate to Los Angeles in order to pursue film and TV opportunities. After being glimpsed in bit parts in such TV shows as "CHiPs" "The Renegades" and "Cheers" along with the minor part of a stand-up comic in the Bob Fosse-directed biopic Star 80 (1983), Keenen found his first real break in the sudsy ensemble TV military series For Love and Honor (1983) as Army Pvt. Duke Johnson, part of an artillery unit who aspired to become a professional boxer. From this, he moved onto more visible roles on nighttime TV, including "Hill Street Blues," "Benson" and "A Different World."

After hooking up with star comedian Eddie Murphy and earning a writing credit for the opening sketch of the star's raunchy live performance documentary Eddie Murphy: Raw (1987) and a TV writing nod for Joan Rivers's nighttime chat show The Late Show (1986), Keenen's name became known as an actor and writer. Partnering with actor/writer/producer/director Robert Townsend, he had his first film hit with the film Hollywood Shuffle (1987), a biting satire highlighting the plight of the black actor in 70's Hollywood. Done in hilariously stereotypical fashion, one great bit had detective Townsend battling a blaxploitation villain named Jerry Curl (Wayans). Keenan went solo (writer/director/star) for his next similar 70s blaxploitation parody, the even bigger hit I'm Gonna Git You Sucka (1988). Here he played the revenge-minded, but not particularly macho Jack Spade alongside such icons of blaxploitation cinema as Jim Brown, Isaac Hayes, Bernie Casey and Antonio Fargas, as well as several members of his family.

These two major successes led to the irreverent, controversial, Emmy-winning TV satire In Living Color (1990). This Fox show would become Keenen's creative baby and prized pièce de résistance that would effectively showcase his deviously scathing social humor. He also turned the show into a family act as well with Damon, Kim, Marlon and Shawn all part of the wild and woolly ensemble. Opening each episode surrounded by the beautiful dancing "Fly Girls" (one of the season's replacements would be Jennifer Lopez), the nattily-dressed Keenen would graciously spotlight his comedy troupe more than himself. The show caught on quick; however, squabbles with the network over creative control, censorship and financial issues led to an incensed Keenen abruptly leaving his show in 1992, after only two seasons. His exit was quickly followed by his family performers.

When it comes to outrageous satire, Keenen has few peers and immediately picked up where he left off as a writer, director and star of in his own film comedy vehicle, the action-filled A Low Down Dirty Shame (1994) in which he plays a private detective named Shame who takes on drug lords. He next supported brothers Shawn and Marlon with a bit role as a mailman in their own popular crime comedy vehicle Don't Be a Menace to South Central While Drinking Your Juice in the Hood (1996), then was given the chance to hang opposite action star Steven Seagal in Seagal's producing vehicle The Glimmer Man (1996) as two cops out to solve some murders. With his next film vehicle project, Keenen decided to write but left the directing chores to David Hogan in a dramatic change of pace with Most Wanted (1997). He plays a Marine and special operations officer on a top secret mission who gets framed for an attempted assassination.

Towards the end of the 1990's Keenen attempted his own nighttime talk show, described as ("late night talk the Wayans way"). As host, writer and executive producer, The Keenen Ivory Wayans Show (1997) had heavy competition and did not catch fire, barely lasting a couple of seasons. Come the millennium, however, Keenen set his sights on directing (and appearing in a minor role) the riotously crude horror film spoof Scary Movie (2000), which prominently displayed brothers Shawn and Marlon (also co-writers). This would become a blockbuster hit. The following year he also directed the first sequel Scary Movie 2 (2001).

Continuing to keeping things more or less a family affair, he directed and co-wrote (only) Shawn and Marlon's crime comedy vehicles White Chicks (2004), as two FBI agents who go undercover in drag, and Little Man (2006), as criminal brothers, one being a dwarf(!); appeared as a guest on brother Damon's sitcom "My Wife and Kids"; and co-wrote and had a featured part in another all-inclusive Wayans project Dance Flick (2009), which mercilessly pokes fun at dance movies. This film was directed by nephew Damien Dante Wayans, co-written by Keenen, Shaun, Marlon, Damien and Craig Wayans, produced by Keenen, Shawn, Marlon, Damien and Craig, and starring nephew Fast Girl (2008) with other performances by Keenen, Shawn, Marlon, Damien, Kim, Craig, niece Chaunte Wayans and nephew Michael Wayans.

After laying low for several years, Keenen, the divorced father of five children, returned to direct several episodes of the comedy series The Last O.G. (2018) starring Tracy Morgan as an ex-con adjusting to the outside.