Tobey Maguire – Fear and Loathing

Those who have seen Fear and Loathing know that Tobey Maguire had an extended cameo in the film. Filmmaker Terry Gilliam asked the actor to go bald for the role, but the Spider-Man star asked for a $15,000 remuneration to lose his hair.

We don’t know what transpired between them, but the end result was Maguire playing a hitchhiker with a terrible haircut. A bald cap and subsequent editing gave the actor a wispy look, so it is safe to say that everything ended well. In hindsight, Gilliam could have just paid the money instead of going through all this trouble!