How many movies have Ben Stein and John Hughes collaborated on?

They have worked on 3 movies together! Their first movie together was Ferris Bueller's Day Off (1986) and was their highest rated movie together. They have not worked together since Dennis the Menace (1993). They are most known for their comedy films together.

Role
Boss
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Producer
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Wichita Airport Rep
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Director
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Screenplay
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Producer
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Economics Teacher
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Director
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Guy Running Between Cabs (uncredited)
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Writer