Spade's movie career was sidetracked by Chris Farley's drug overdose. He's not been able to recreate that Tommy Boy and Black Sheep success. He was pretty good in TV's Just Shoot Me, too.
He apparently has a reputation for dating a lot of hot women. As Adam Corolla has noted, it might be a self-fulfilling prophecy though. When other women see a hot woman with a guy, they sometimes start thinking that he MUST have something going on.
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