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Yeah, for quite some time it seemed they would only cast him to play the arrogant, snobbish, rich kid who usually gets his comeuppance by the end of the movie. I think the first movie that showed he could do considerably more than that was Sex, Lies, and Videotape, but even after that it took a while for him to shake that "rich kid" typecasting.
For me, I knew him as you so well described him - the rich kid with floppy hair in the '80s - then he went away (from my world) until just recently when he came back as a balding, edgier and incredibly talented actor. It was a shock to me, but based on IMDB, he's been working all along.