Al MacAfee – A parody of Joe Louis Clark, David Alan Grier plays a strict, yet clueless shop teacher with a bad hip. He is known for working as a Hall Monitor and using a bullhorn to yell at innocent students and teachers, while being oblivious to bad things going on around him, as well as the consistent rejection by a fellow female teacher (played by Kim Wayans), with whom he is infatuated. Various cast members portray students and teachers who put up with Mr. MacAfee.

Anton Jackson – Damon Wayans portrays a filthy, drunken homeless person (he lives in a corrugated cardboard box) with a unique world view. Amongst other happenings, he appeared in Po' People's Court (taken from The People's Court), had his own Public-access television cable TV show entitled This Ol' Box (taken from This Old House), and had a marriage of convenience. He frequently carried with him his "personal facilities", a jar that he used as a toilet and which seemed to contain a floating pickle and brine (probably meant to represent urine and a turd). The character was also shown on an episode of Saturday Night Live hosted by Damon Wayans where Anton testifies in the O.J. Simpson trial, and was also briefly in 1992's Mo' Money featuring Damon and younger brother Marlon Wayans.

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Cephus and Reesie – Kim Wayans and David Alan Grier play a pair of incredibly annoying soul singers, modeled slightly after Ashford & Simpson. Episodes with Cephus and Reesie included them mistakingly performing at a Bar Mitzvah, an advertisement for an album of theirs, which is eight CDs long due to them breaking songs such as "Silent Night" by one of them asking "If it was a silent now how could it have been a holy night?", and an episode where they sing an extended rendition of "Ain't No Mountain High Enough" for a Death Row convict (Jim Carrey) who (regrettably) is granted his last wish to hear some live soul music before he dies that very night. Cephus and Reesie were also said to have jammed with Frenchie.

Fire Marshal Bill Burns – Jim Carrey portrayed a crazed, masochistic (and supposedly immortal) fire marshal with a manic grin and laugh along with a scarred face whose safety advisories usually include demonstrating (on himself) the very disaster he's warning against. (Every sketch illustrates a timeline of readily-visible damage on Bill from previous episodes). Usually, the warnings are against ridiculous situations that would never come to pass, such as an alien crab-people invasion, a sex doll that was accidentally inflated with hydrogen instead of air which then exploded due to static electricity, or an outbreak of psychotic elves. Every sketch ends with Fire Marshal Bill blowing up the facility he's teaching at, to which the people involved look at the burning facility and either lament what will become of them or simply stare in shock while Fire Marshal Bill says a witty comment and (sometimes) leaves to do more "safety advisories". Despite each sketch showing him lose parts of his body (in one sketch, only his head remained), Bill never dies. In about half the sketches, he gave his full name as Fire Marshal Bill Burns. In one episode when on a cruise, he had a blonde wife named Ashley (a play on the term ash) who also was seemingly immune to the damage Bill caused. Her face was similarly scarred like Bill's was and she was a party to his demonstrations (spreading gasoline in a life raft to prove Bill's point about the danger of flare guns). His catchphrases included "Lemme show ya something!!", "Don't worry folks, I'm a Fire Marshal!" and "It can be very, very DTUHHH-DTUHHH ... DEADLY!"

Homey D. Clown – Damon Wayans plays an ex-con who works as a clown (real name Herman Simpson) for his parole agreement, but lashes out at anyone (usually by hitting them on the head with a sock full of pennies) who attempts to make him perform the standard antics of the role - "I don't think so! Homey don't play that!". His goal in life is to get even with "The Man", a personification of the white males that are "holding him down". Near the end of most sketches, Homey would lead a group of children (played by the cast members) in a call and response sing-along, which would end with him degenerating into a rant, then intimidating the children into repeating after him. Homey was also the first, and only, In Living Color character to get his own video game.[2]

Sweet Tooth Jones – A send-up of blaxploitation films; Tommy Davidson plays a karate instructor with a balding Afro haircut who runs the "Hollywood School of Self-Defense", assisted by Sugar Bear (Marc Wilmore) and Queen Bee (Alexandra Wentworth), all of whom wear clothing from and speak slang of the 1970s, completely out of place with the people they are instructing. Running gags would include simulated the fight to knock out his assistant, but never really knowing how to actually fight. As he put it, "I am a fight choreographer!"

Vera de Milo – Jim Carrey portrays a steroid-abusing female bodybuilder with a conspicuously flat chest and bulge in her posing trunks. Vera was best known by her unnaturally deep, breathy voice and grotesque, horselike laugh, along with a small set of pigtails. Vera de Milo often appeared in movie parodies of then-current films like Pretty Woman and The Hand That Rocks the Cradle.

Wanda – Jamie Foxx portrays Wanda Wayne, the ugliest woman in the world...so ugly, in fact, that no one wanted to be in the same room as her (in one episode, Dracula exposed himself to sunlight to get away from her). She supposedly is the long lost member of the group En Vogue but left because she was taking all of the men. One of these helpless individuals is often Tommy Davidson. In the final season of In Living Color, Wanda had a child out of wedlock and searched for the father of her child Wanda Jr., which ended with her chasing after Barry Bonds' limo driver, who she believed was the father. Trademark phrase: "I'm gon' rock yo world," "I'm red' to go!," "Hey fo' real do," "I got you," and "Don't make me get ugly!"