2. Michael Jordan

Ride: Gulfstream IV private jet, 1991
Complex Says: Throughout his storied career, as arguably the greatest player in NBA history, Michael Jordan, aka “His Airness,” consistently dominated when taking flight to the basket. In his life after basketball, Jordan still manages to make his mark in mid-air with his multi-million dollar Gulfstream IV private jet. Bearing the colors of MJ's alma mater (UNC), this not-so-ordinary-looking plane is adorned with the unmistakable Jumpman logo on its rear fin and the inscription “N236MJ” on the engines. This symbolize Jordan's jersey number and six world championships.