Career: 1987-2004
'90s Team(s): Chicago Bulls (1990-98), Houston Rockets (1999), Portland Trail Blazers (1999)

In 2011, he won the coveted NBA Celebrity All-Star MVP by outplaying heavyweights like Jason Sudeikis, Rob Kardashian, and Justin Bieber. For his day-job, he's a senior advisor to Michael Reinsdorf, the Bulls' president and COO. Like Glen Rice's ex, Scottie's wife Larsa is on The Real Housewives of Miami.

Currently, Scottie is being sued for $4,000,000 by Camran Shafighi after Shafighi pestered Pippen with calls for autographs and began snapping pictures of him at the Malibu restaurant Nobu. Pippen claims the guy was drunk and called him the 'n-word' and then spat on him. Earlier in the night he even sat at Pippen's table when a guest got up to drop a pile. Either way, Shafighi looks like kind of a douche (a term that won't come up in the court proceedings). If someone called us a racial slur and spit on us we would knock them out too.