After a brief stint in Las Vegas, Brady headed to Hollywood where appearances on episodes of the NBC series "I'll Fly Away" and "In the Heat of the Night" helped him make his small screen entry. He was featured in the Disney Channel TV-movie "On Promised Land" in 1994 and went back to the stage, where he was becoming known for his improv skills. In 1997, he tried out for the British TV series "Whose Line Is It Anyway" and impressed producers, who would cast him in four of the season's episodes. A half-hour of high energy improv games performed in front of a studio audience and aired on television, the one-of-a-kind series was duplicated for American television with Drew Carey as the host in 1998, and Brady was picked to be a regular on the new series. Fielding the most ridiculous of situations with aplomb and an inclusive but sharp sense of humor, Brady was appropriately quick-witted and fast on his feet and particularly excelled in the very popular singing and dancing events, quickly becoming an audience favorite with this dependably clever and uproarious take on events such as the storytelling "Hoedown" and "Greatest Hits", an often absurdist spoof of compilation album TV commercials.

Thanks to his enormous success on "Whose Line Is It Anyway?" Brady had become a fixture in many an American household, and was received warmly at "The 52nd Annual Primetime Emmy Awards" in 2000, where he performed a song medley. That same year he played Lazardo the magician in ABC's "Geppetto", featuring Carey in the title role. In the fall of 2001, Brady landed his own series, the aptly titled "The Wayne Brady Show", a comedy/variety show on ABC.