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Goaded into entering a male beauty pageant while studying economics at Rutgers University, Bellamy had to decide on a routine for the talent competition and wrote a short comedy act that wowed the crowd. Excited by the reaction, he decided to pursue a career in stand-up and began performing in clubs in 1988. In 1990, Bellamy made his national TV debut on the NBC series "It's Showtime at the Apollo", winning over what is largely believed to be one of the toughest audiences for an obscure performer. Quickly making a name for himself in the business, Bellamy headlined the Def Comedy Jam National Tour in 1992 and was featured that same year in the "HBO Comedy Hour" presentation "The 15th Annual Young Comedians Show -- Hosted by Dana Carvey". 1993 marked Bellamy's debut on the big screen, appearing in the features "Who's the Man?" and "Joey Breaker".
Credited with coining the now-common phrase "booty call" (insisting that a late-night phone call is a universally understood invitation for an intimate interlude), Bill Bellamy had a Showtime special bearing the name with 1994's "Bill Bellamy: Booty Call". That same year he began his five-year run as a VJ on MTV, hosting spring break specials and other shows in addition to "MTV Jams". Balancing suave and silly, the appealing host won many fans on MTV, both in the audience and in the music community. With the added exposure that MTV afforded, Bellamy's career began to really take off. In 1996, he had a small supporting role in the actioner "Fled", while 1997 saw him with two featured big screen roles. In "Love Jones" he played smooth Hollywood, a formidable romantic rival, while in "Def Jam's How to Be a Player" he went for laughs as a womanizer who tries to balance seven women in the course of one evening.
Having already become established as a charismatic performer, Bellamy would begin to show impressive versatility. 1999's "Love Stinks" saw him in wedded bliss with Tyra Banks while that year's "Any Given Sunday" cast him in his most physically and emotionally challenging role up to that point, playing a cocky and flamboyant football star addicted to drugs. A guest role on "The Jamie Foxx Show" reteamed him with his "Any Given Sunday" co-star in 2000. Alongside Morris Chestnut, Shemar Moore and fellow comic-turned-actor D L Hughley, Bellamy starred in "The Brothers" (2001), an ensemble piece about four African-American professionals and their romantic trials. Bellamy showed his serious side in some scenes, and proved his acting chops with a turns as the marriage-phobic attorney Brian. More down-to-earth than his onscreen counterparts, Bellamy realized the power of his influence and happily took a voice role in the positive children's series "Cousin Skeeter" (Nickelodeon, 1998- ), bringing life to the titular little puppet with a big mouth in the midst of a live-action family.
After a small role in the football film "Any Given Sunday" in 1999, Bellamy got a starring role in the phenomenally successful ensemble drama "The Brothers" in 2001. However, in 2002, Bellamy got perhaps the biggest break of his career with the Fox TV drama "Fastlane." Bellamy starred with Peter Facinelli as a detective team that investigates illegal operations before they blow up into police cases. The role offerred Bellamy a chance to showcase his talent in a sustained and starring role in the ever-popular black/white buddy cop genre. In a unique opportunity, Bellamy got the chance to try out the dynamic on the small screen in a drama setting, instead of a one-shot action film.