Year (of Sneaker): 2006
Entourage is by defintion a show about sharing the wealth, but Vince hit his peak here (OK maybe second to that time he saved Turtle from stupidly selling his tequila stocks and made him a millionaire). Feeling guilty that his decision to wait on line with everyone else and not cash in on his celebrity status cost Turtle a pair of limited edition kicks, Vince has renowned sneaker design guru Fake Nigo Fukijama make Turtle an even rarer pair, for a grand total of $20,000. And it wasn't even his birthday. The Mark Smiths (the actual designer) are not quite as rare in real life, at one point bidding on eBay reached about half of what Vince paid in-show.