In the years since I worked with John Hughes, there were many years where I literally had hundred of doors slammed in my face because I wasn't that kid anymore, and I wasn't a character actor, and I wasn't a leading man, and I wasn't whatever Hollywood was looking for.

Hall joked that the two were "in Africa with Dave Chappelle. After a series of minor roles in the 1990s he starred as Microsoft's Bill Gates in the 1999 television film Pirates of Silicon Valley. He was cast as Brian Johnson "the brain" in the quintessential teen film The Breakfast Club co-starring Emilio Estevez Judd Nelson Ally Sheedy and Molly Ringwald.

Hall's next movies with Hughes were the teen classics The Breakfast Club and Weird Science both in 1985. During its run the show was one of the highest-rated cable television series.