Woolridge was selected sixth in the 1981 NBA draft by the Chicago Bulls, where he played for his first five seasons. Woolridge made his NBA debut on November 7, 1981. Woolridge was named NBA Player of the week on December 9, 1984. During the 1984–85 season, Woolridge averaged 22.9 points per game and combined with rookie teammate Michael Jordan to average over 51 points per game. Prior to the Jordan era, Woolridge was one of the Chicago Bulls' marquee players along with Hall of Famer Artis Gilmore, Reggie Theus and David Greenwood. At tall, and weighing , Woolridge was one of the most gifted dunkers in professional basketball. Woolridge was also one of the original alley-oop artists. Woolridge competed in the NBA Slam Dunk Contest in 1984 and 1985, surpassing the scores of Clyde Drexler and Michael Cooper. Woolridge led the Chicago Bulls in scoring in 1986 and was the last player to lead in scoring before Jordan took over. While unstoppable on the open court, his one-dimensional play did not complement Jordan's skills.