25. Chris Brown
While some consider him to be one of the most despicable sleazebags in the music business, plenty continue to enjoy his music, at least to the extent that he can continue a lavish lifestyle. Chris Brown owns a couple of Porsches, a customized Range Rover, a Lamborghini Aventador that is painted to look like a fighter plane, and a Bugatti Veyron.
Not only is he a talented rapper, but T-Pain also owns his own custom auto shop in Atlanta. He has a few cars, all of which are roughly immaculate. He has a Fiat 500, a Rolls Royce Ghost that is thoroughly customized, and of course he used to have a Bugatti Veyron, because what is a car collection without one of those. Over the years, T-Pain has had dozens of cars. It is hard to keep track of which whips he has kept around. He also has a Rolls Royce Ghost that he calls “Raymond”, and a couple of vintage Impalas.
23. Janet Jackson
The youngest of the Jackson family makes our list as the proud owner of an Aston Martin Vanquish. The talented singer and performer Janet Jackson, also owns two Lamborghinis and a white Bentley Continental GTC. Quite impressive.