3. Darius McCrary
As the eldest Winslow, Eddie, Darius McCrary was one of 90s TV coolest teens (just check out his sweet vest and overalls combo). After Family Matters ended in 1998, he appeared in numerous TV shows and films and even provided the voice of Jazz in the Transformers movie. Now McCrary is a soap opera star — since 2009 he has played Malcolm Warner on The Young and the Restless.