Cars: Rolls-Royce Phantom Drophead Coupe, 1969 Impala, Scion xB, Mini Cooper, Ferrari F430, Bugatti Veyron, Cadillac Hearse, 1972 Chevrolet Impala, Oldsmobile 442, 1991 Chevrolet Caprice Classic, 1963 drop-top Chevrolet Impala, 1963 hard-top Chevrolet Impala, Ford F650, Buick Lacerne, 1972 Chevrolet Chevelle

You know how you can tell a pure-bred automotive enthusiast? When they own various years of the same car and explain to you how not just the aesthetics are different, but how the engine is different. Forbes wrote an article about T-Pain back in 2009 and he had 32 cars in his possession at that point. We're not sure if he's sold any since then, but we know for sure that he's made some more purchases.