Additionally, Gleason played the villainous Clarence Beeks, the Duke brothers' security consultant and fixer, in the 1983 comedy Trading Places starring Dan Aykroyd and Eddie Murphy.

Gleason played the disciplinarian Vice Principal Richard Vernon, in the 1985 coming-of-age film The Breakfast Club opposite many members of the Brat Pack.

The film has been noted as one of the most prominent and well-remembered of its genre,[9] and many reviews praised Gleason's performance as the vice principal who was frequently at odds with members of the titular group, particularly Judd Nelson's John Bender.

In an on-set interview, Gleason spoke at length about the skill of the teenage actors he worked with, adding that he believed he "could never have been as good at [their] age.

He directly parodied his Breakfast Club role in the 2000 A-Teens music video for "Dancing Queen" and in the 2001 comedy film Not Another Teen Movie.

"[11] Gleason was known to Star Wars fans for his role as Jeremitt Towani in the 1985 made-for-TV film Ewoks: The Battle for Endor.

In 1988, Gleason played Deputy Police Chief Dwayne T. Robinson in the Bruce Willis action film, Die Hard.

In his review of the film, critic Roger Ebert described Gleason's character as having "one purpose: to be consistently wrong at every step of the way," [12] and as a foil for Willis and Reginald VelJohnson.