1996–2001, UPN. After being passed over by CBS, UPN picked up this show about a high school student in Los Angeles, and it went on to be one of the network's biggest successes. Brandy played the titular Moesha, and the character's large group of family and friends populated the "comedy" that often dealt with issues such as teen pregnancy, premarital sex, racism, and drug use. Brandy's brother Ray J., of banging Kim Kardashian fame, joined the cast in the last two seasons. The show also featured an impressive array of '90s hip-hop and R&B stars, including recurring love interest Usher, and cameos from Mary J. Blige, Boyz II Men, A Tribe Called Quest, Tyrese, DMX, Lil' Kim, Mo'Nique, Doctor Dre, Ginuwine, and more.