Webb played college basketball at Midland College. He is noticed as winning the slam dunk contest, despite being one of the shortest players in NBA history at 5’7”. Most people were surprised of he participated in the 1986 NBA Slam Dunk Contest because of his height. His dunks included the elevator two-handed double pump dunk, the one-handed off the backboard one-handed jam, a 360-degree helicopter one-handed dunk, a 180-degree reverse double-pump slam, and finally, the 180-degree reverse two-handed strawberry jam from a lob bounce off the floor.