A 6'1" guard from Jacksonville University, Brown was selected by the Celtics with the 19th pick of the 1990 NBA Draft. He was a member of the NBA All-Rookie Team in his first year, when he played in all 82 games and averaged 8.7 points per game. One of the highlights of his career occurred in 1991, when he won the NBA Slam Dunk Contest with a "no-look" slam dunk. He was a starter for Boston in during the 1993-94 and 1994-95 seasons and posted his best scoring numbers, averaging more than 15 points per game each of those years. Overall, during his career, he scored 6,758 total points.

Brown later served roles in the Women's National Basketball Association first as a head coach for the Orlando Miracle and then as the head coach for the San Antonio Silver Stars. In 2005 he won a one-year contract as a studio analyst for ESPN as the winner of the reality show Dream Job, defeating former Houston Rocket Matt Bullard. He went on to host a ESPN show called City Slam!

In September 2011, Brown announced that he would be joining the Detroit Pistons as an assistant.