Think outside of the box. Damon Wayans often creates unconventional characters like the "Head Detective" from "In Living Color." As a Mr. Potato Head version of a police detective, this character was featured in numerous sketches through the run of the show.
Embrace controversial material. More than one character Damon Wayans created was the subject of network censorship and public outrage. One example is Damon's "Handiman" character (later the inspiration for the movie "Blankman"). This physically challenged superhero who drools uncontrollably understandably drew some objections.
Impersonate famous people. Damon's impersonation of Louis Farrakhan from "In Living Color" is legendary. He also impersonated Babyface, Little Richard, Redd Foxx, Richard Pryor and Vanilli from Milli Vanilli throughout his career.
Commit to the character you develop. Damon rarely ever breaks character during a scene and is known for going all the way to play every character authentically, if exaggeratedly. For example, when portraying the character of "Blaine Edwards" from "In Living Color," Damon dons a miniature beret to play an effeminate gay movie critic opposite co-star David Alan Grier.
Give your character an unexpected twist. Several notable Damon Wayan's characters play against type such as the incorrectly articulate prison inmate, Oswald Bates and the angry ex-con kid's party clown, Homey D. Clown. To develop characters like these, take a stereotype and reverse it to create irony.
Review Damon Wayans' performances in the first three seasons of "In Living Color" to study the characters he made famous (see Resources below).