7 Comedians Who Completely Botched Their Transition to Film

5. Tom Green

Freddy Got Fingered. Does anything else really need to be said about Tom Green's movie career? His comedic personality was so absurd (and so well-known) that whatever film role he chose had to be imbued with the same level of absolute insanity, or audiences would start crying "sell out." Finding a way to make that even moderately palatable was the real challenge. It worked fine in moderation, adding a bit of sublime weirdness to the otherwise unimaginative Road Trip. But as the main focus...? With Freddy Got Fingered, which Green also wrote and directed, every gross out tactic he'd ever utilised on The Tom Green Show was thrown at the wall to see what would stick. Less an actual movie and more a series of brutally disgusting acts spliced together to fill 90 minutes, Freddy Got Fingered made a strong case for keeping Tom Green off movie theater screens for the foreseeable future.