Tyler Perry
Tyler Perry may very well be the last known guy on this list, but he’s certainly not the least successful.
Perry owns his very own Gulfstream III, which initially cost him an estimated $65 million plus another $55 million to modify it. It’s said that the plane is more like a high-level show car than a plane you use to take you around the globe, sporting a home theater system considered by many as one of the best in the world.