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via Flickr/ Gage Skidmore.
Writer-director Richard Kelly met with then 31-year-old Vince Vaughan 4 times in an attempt to get the post-Swingers actor to take on the titular role, but Vaughan was uncomfortable with the idea of playing a 16-year-old. Bizarrely, Mark Wahlberg was also interested in the role but only if he could play Donnie with a lisp!