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If you’re younger than 30, then you probably recognize actor Alan Rickman as Snape from the Harry Potter movies. But if you were of prime moviegoing age in the late 1980s, you may know him best as Hans Gruber, the ruthless villain in Die Hard. In the meantime, he also starred as the scheming Sheriff of Nottingham in Robin Hood: Prince of Thieves.

Alan Rickman, who died this week at age 69, played a multitude of roles during his 45-year career. But he was never more memorable than when he was playing the bad guy. This video recalls some of his most iconic characters.