5. Adam Sandler - Donny Donowitz (Inglourious Basterds)
The Role: And here comes possibly the most eyebrow-raising casting pick on this whole list. That's right, Tarantino's original choice for Eli Roth's baseball bat-swinging soldier Donny "The Bear Jew" Donowitz was Adam freaking Sandler. What Happened?: Sandler had a scheduling conflict with Judd Apatow's Funny People, so had to give up the Basterds role. Given Sandler's part in Funny People was a starring role (and probably paid more), it makes sense. Would It Have Worked?: It's hard not to be curious about this one, and while Sandler's batting average is terrible, he is one of those actors who can be fantastic when he wants to, and often needs a strong director like Paul Thomas Anderson or Apatow to whip him into shape. Tarantino clearly saw something in him that he could harness (as well as being his buddy), and it certainly would have added to the hilariously surreal tone of the picture. A cautious yes for this one.
Jack Pooley
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Stay at home dad who spends as much time teaching his kids the merits of Martin Scorsese as possible (against the missus' wishes).
General video game, TV and film nut. Occasional sports fan. Full time loon.
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