Rupert Pupkin (The King of Comedy)

If you've ever wondered how unnerving dedication looks wrapped in a polyester suit, meet Rupert Pupkin from The King of Comedy. This guy turns creepy fandom into an art form. Seriously, his relentless pursuit of fame could give anyone a run for their money in the 'Greatest Robert De Niro Performances of All Time'. And let's not forget the late-night debates—'Is Rupert genius or just plain scary?' Trust me, this is the kind of stuff you argue over beers and it never gets old.