Enrique Iglesias – Net worth: $100 Million- Gulfstream IV,  Estimated $40 Million

Latin crooner Enrique Iglesias gets to fly a lot as he is still being in demand as a performer – which is just fine with him because he loves planes, and is, in reality, a certified pilot of small to medium planes, and helicopters. So though he doesn’t pilot his Gulfstream IV private jet, he could. But then again, being a passenger is more relaxing and in that way, he won’t get to locations tired and be able to give peak performance toward more money in his account.