Reid was born in The Bronx, New York City, to a Jamaican father (1931-) and an Irish mother (1930–1973). He graduated from the Bronx High School of Science in 1982. He also graduated from Lehman College in the Bronx.
He is best known as one-half of late-1980s/early-1990s hip hop musical act Kid 'n Play with fellow rapper/actor Christopher "Play" Martin. Reid was particularly notable for his extreme hi-top fade hairstyle. Reid has appeared on a number of television programs, including Martin and Sister, Sister, and has also served as the host of amateur contest shows such as Your Big Break and It's Showtime at the Apollo. Reid tours as a stand-up comedian.
Reid's most recent musical contribution has been writing the theme song to HBO's Real Time with Bill Maher. He also appeared on the VH1 reality magician game show Celebracadabra in 2008. Pursuing a solo career, in May he released a music video for a song called "Why Don't You Stay" to which he raps and sings on the track. In the same year, he appeared in The Asylum's film War of the Worlds 2: The Next Wave, a sequel to H. G. Wells' War of the Worlds.
He has also been a guest on The Dawn and Drew Show, Comics Unleashed, New England Sports Network's Comedy All-Stars and Slanted Comedy.
He plays the role of "The Rhymer" on the Nickelodeon TV series Supah Ninjas.
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