2. Willhelm - The Brothers Grimm
Terry Gilliam's mess of a film, The Brothers Grimm, stars Damon as one half of the titular sibling pair, Wilhelm, in a tale that depicts them as con-artists in Germany, when they are faced with a curse which will require them to rise to action. Charismatic and charming though the performances from Damon and co-lead Heath Ledger are, there's just no escaping the fact that Gilliam's film is, as so many of his are, complete style over substance and little more. Unsurprisingly, Damon was not the first choice for Willhelm - it was Johnny Depp - but Bob Weinstein didn't believe Depp commercially viable enough, something Damon openly mocked when Depp's Pirates of the Caribbean franchise blew up half-way through filming. Still, it could have all been worse; Damon was originally supposed to wear a fake nose, too, and the experience couldn't have deterred Damon that much, because he's starring in Gilliam's upcoming The Zero Theorem, wearing a profoundly silly white hairpiece to boot.