OK, we'll admit it: This one's like taking broccoli away from a fat kid. Jamie Kennedy—the second coming of Pauly Shore—has never claimed to be a great actor, nor has he starred in any movies presented as anything more than cheap entertainment. When you're a comedian who can't sell a single joke in any movie, however, a hater's blind eye must open wide. We've seen (and actually liked) his critic-skewering 2007 documentary Heckler, so we'll play nice this time; as Heckler puts on blast, Kennedy is one of Hollywood's easiest targets, and he knows it. But, hey, at least he got to date above his league with Jennifer Love Hewitt for a hot minute. That's a fine consolation, no?
23. Jamie Kennedy
Worst Performances: Bowfinger (1999), Malibu's Most Wanted (2003), Son Of The Mask (2005)