54. Nike SB Dunk High "Pee Wee Herman"
Year Released: 2007
As it's known, Pee Wee Herman (Paul Reubens) went to jail for getting a little touchy at a movie theater. With the already controversy Nike SB added this shoe to its "Fallen Heroes Pack" which took iconic controversies and forever immortalized it into a shoe. The shoe matches his suit to the the T, but it's what's on the insole that tells you the whole story.