25. Reebok RBK S. Carter

Release Date: 2003

Back when a big dude from Carroll City named William Roberts II was still trying to get put on, the biggest rapper in the universe signed an endorsement deal with Reebok. Jay-Z wasn't expected to actually wear Reebok all the time - an unprecedented agreement - but he was going to get a signature shoe, which he, er, loosely based on the classic Gucci tennis shoe. The excitement faded pretty fast, but the originals were plenty anticipated.