18. Jake Gyllenhaal In Giving Up The Gun - Vampire Weekend
None other than Donnie Darko himself, Jake Gyllenhaal, turns up in Vampire Weekend's Giving Up The Gun from 2010, proving that he doesn't take himself too seriously. Playing an incredibly arrogant looking 80s stereotype, he's part of an indoor tennis tournament officiated by RZA. Once again, there's more than one celebrity cameo here. Besides Gyllenhaal, and RZA, there are appearances by Lil John, Joe Jonas, and possibly Daft Punk, though who can really tell.