Comedy Central Presents: Sheryl Underwood

Sheryl Underwood takes the stage with a combination that makes her stand out in the early 2000s stand-up scene: she is an unapologetically blue, sex-positive Black comic who also happens to be a card-carrying Republican. Filmed at the Hudson Theatre in New York City, this half-hour set highlights her ability to make audiences uncomfortable and entertained in equal measure.

By 2003, Underwood was a seasoned headliner and BET ComicView veteran, but her outspoken conservative leanings made her a rarity in the mainstream. She details her fondness for President George W. Bush and outlines her thoughts on everything from Catholic Church scandals to proper skin exfoliation. She also transitions into highly frank, physical comedy about the indignities of dating, proving that her political registration does not stop her from delivering a dirty, fast-paced set.