Underwood first gained public notice as the first female finalist in the Miller Lite Comedy Search in 1989. She won the BET "Funniest Female Comedian on Comic View" award in 1994 and the BET Comedy Awards' Platinum Mic Viewers Choice Award in 2005. Following her stand up success, Underwood took a number of minor acting roles including Bad Mouth Bessie in the 1998 film I Got the Hook Up, and Catfish Rita in the 2005 film Beauty Shop.
Underwood was the host of BET's Comic View and executive producer and host of the limited run comedy/variety series Holla(September 2002 – January 2003).
Underwood was a contributor on the nationally syndicated Tom Joyner Morning Show until June 2010 when she jumped ship toThe Steve Harvey Morning Show to be their contributor. She briefly hosted her own radio program, "Sheryl Underwood and Company" for Radio One-owned Syndication One News/Talk and XM Satellite Radio's Channel 169 (The Power ). On Tuesday nights, Underwood hosts The Sheryl Underwood Show on Jamie Foxx's Sirius Satellite Radio channel, The Foxxhole (Sirius 106) In 2011, she joined the popular daytime show The Talk in its second season replacing Leah Remini.