After we saw Will Ferrell in Stranger Than Fiction on Thanksgiving, (which I quite liked) we were talking about other comedians' first (and/or notable) forays into dramatic roles, and how Stranger Than Fiction compared to the others. Here are some we came up with:
Ben Stiller in Permanent Midnight (same year as Your Friends & Neighbors, but I hate that movie; Reality Bites and Flirting with Disaster were both earlier, but not as good as Permanent Midnight)
Brendan Frasier Gods and Monsters
Adam Sandler Punch Drunk Love (looking back, I'm not sure that movie holds up)
Jim Carrey Eternal Sunshine of the Spotless Mind (ok, Truman Show was way before, but nothing holds a candle to Eternal Sunshine)
Bill Murray Lost in Translation (yes, all Wes Anderson movies, yes Ed Wood; I never saw The Razor's Edge)
Yeah, yeah, Robin Williams. I'm too lazy to look up his films, whatever.
Please add your faves!