Bentley was born Derek Watkins in Atlanta, Georgia. He attended North Atlanta High School. He is a graduate of Morehouse College with a Bachelor of Science degree in biology and attended the Fashion Institute of Technology in New York City. His younger brother, Dion, is a recent graduate of University of Southern California`s film school. His cousin, Jonathan Watkins plays in the drumline at Auburn University. His uncle, a band director, played him Beethoven`s 5th Symphony at 18 months and, by the time Watkins was 2-1/2 years old, he was learning to play violin via the Suzuki Method. He would later become concert master in his high school orchestra. Watkins gained an appreciation for dance and fashion in Atlanta. After graduating from Morehouse, with a bachelor of science degree, he took a job at a local Polo store in Atlanta where his customers included his childhood friend Andre 3000 of Outkast and future employer Sean "P. Diddy" Combs. When offered a job at The Polo Mansion, Watkins relocated to New York City, where he encountered Combs. After leaving Polo, Watkins became an apprentice for designer Alan Flusser. Later he was maître d` at a New York restaurant. Watkins later reconsidered his position as maître d’ and sought a career in entertainment. He was later hired as Combs` personal assistant. Watkins worked for Combs for two years. In 2002 he resigned as Combs` personal assistant to pursue an acting career.

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