Bryant made his acting debut in 1996, appearing in an episode of "Moesha". He met the show's star, Brandy, earlier in the year at a Nike All-Star basketball game, and then a couple of months later in May 1996, Brandy was Bryant's date to his high school senior prom. That same year, he guest starred as himself on an episode of "Arli$$" (episode: "What About the Fans?") and "Sister, Sister" (episode: "Kid-Napped"). In 1997, he appeared on an episode of "Hang Time", this was followed by a guest appearance on the Nickelodeon sketch comedy series "All That" (1998). Bryant was also the first choice for the role of Jesus Shuttlesworth in Spike Lee's 1998 film "He Got Game", but he turned down the role, saying "this summer is too big for me."