He came into the League as a rapping, acting, Reebok-wearing, Pepsi-drinking, breakdancing 20-year-old who was pretty good at basketball, too. In many ways, Shaquille O’Neal paved the way for business-minded players like LeBron James. Michael Jordan may have been the first person to endorse everything but condoms (you’re welcome for that link—check pg. 50), but it took him a championship or two to get to that point. Shaq broke into the L with Wilt-like potential and instantly had a $70-million deal with Reebok. He was also letting the poor sap(s) who wrote the script for Kazaam earn a living. Shaq’s tenure with Reebok was a short one, but he’s always had attention-grabbing sneaks on his feet, regardless of the brand.