Keenen Ivory Wayans left the show in the middle of the fourth season over disputes with Fox about censoring the show's content and rerunning early episodes without his consultation. At the end of the season, Kim Wayans and Shawn Wayans followed their brother in leaving the show. Damon Wayans had already left the show at the end of the third season to pursue his film career, and Marlon Wayans left the show after the 12th episode of the fourth season.
Ugly Wanda, played by Jamie Foxx, was based on a character LaWanda Page played in a sketch on Redd Foxx (1977). The first sketch to feature Wanda, in which she gives an erotic massage to a man who hasn't seen her face, is a remake of the original sketch. The character was named after Page. Jamie took his stage surname as a tribute to Redd Foxx, and used an androgynous first name because he believed women were more likely to get picked off the sign up sheet during open mike nights.
The controversial dialogue during the "Men on Football" sketch in the live Superbowl Half-Time Party special was mostly ad-libbed.
Damon Wayans's character Homey the Clown was based on writer Paul Mooney. Mooney is a comedian known for his angry rants and frequently uses the word "homey."