After attending Midland College and North Carolina State University, he was the 4th round draft pick by the Detroit Pistons in the 1985 Draft. In 1986, Webb entered the NBA Slam Dunk Contest, and despite being the shortest, had the highest jump of 42 inches and went on to win the contest.
He spent most of his time with the Atlanta Hawks, playing six seasons with the team. Statistically, Webb had his best seasons with the Sacramento Kings where he was a starter from 1992-1995. In 1998, Webb retired from basketball after playing just one season with the Orlando Magic.
He played 814 games total and scored 8072 points throughout his entire career.