Always able to make friends and family laugh, Underwood took her talents to the stage in the late 1980s. There she discovered she could make others laugh, too. That talent was recognized when Underwood was named as the Miller Lite Comedy Search's first female finalist in 1989. A few years later, Underwood would go on to win the BET "Funniest Female Comedian on Comic View" award. She also hosted the comedy/variety show for a period of time. Underwood's win - as well as her quick wit and charismatic personality - caught the attention of the BET network. They took up Underwood on her pitch to produce and host Holla, a panel talk show in the vein of Bill Maher's Politically Incorrect. The show ran for a limited time in 2002. Though the show was short-lived, it showcased Underwood tested her acting chops in two well-known films, I Got the Hook Up and Beauty Shop with Queen Latifah, a spin-off of the popular Barber Shop franchise.