Seth Green, Radio Days (1987): Woody Allen the character is such an iconic screen figure—close to The Little Tramp, really—that it’s sometimes hard for Woody Allen the filmmaker to do without him, even when he has no interest in embodying him personally. (The exception is dramas, where his protagonists tend to be fresh creations.) For his delightfully nostalgic look at his Brooklyn childhood in the ’40s, the Woodman cast a young kid named Seth Green. And though he’s literally playing the young Woody Allen, Green does not act like his director. According to this film, the young Woody was a well-adjusted, basically normal kid.
John Cusack, Bullets Over Broadway (1994): Woody was approaching 60 when he made this Roaring Twenties farce, so he was unable to play the young, screwed-over playwright lead. And though the role as written isn’t overtly Woodyish, he decided the actor playing him—John Cusack—should do an imitation of him. A very bad imitation. Luckily a lot of fine (and often Oscar nominated) performances surround him.
Kenneth Branagh, Celebrity (1998): Luckily for Cusack, Branagh’s worse. The Brit has a gift for American accents—see: his spot-on Southern twang in The Gingerbread Man—but he can’t pass as a nebbishy, nasal-voiced Jew.
Jason Biggs, Anything Else (2003): There are few actors less Woody Allenish than the Jersey kid known for fucking pies, but that’s the point of this fascinating failure. Biggs plays a character who’s one of many young aspiring neurotics who look up to Woody Allen. Except that, at least according to this film, Woody isn’t really like his image. Woody plays Biggs’ mentor—an aging, struggling artist who is actually filled with rage, having curdled into a bitter freak. The message: don’t be Woody Allen, kids.
Will Ferrell, Melinda and Melinda (2004): A bad idea and the best part of a wretched mess.
Owen Wilson, Midnight in Paris (2011): Owen Wilson is fundamentally incapable of sounding like anyone but Owen Wilson. His whine is his own, and his laid-back mien softens an impersonation that’s usually played coarse. He’s the pleasant, inoffensive center of a pleasant, inoffensive film.