Steve Harvey – Bentley Mulsanne, Estimated $305K

Most times when you see Steve Harvey, he’d be wearing that big wide grin on his face. His life wasn’t always so happy, though. At one point in his life, Harvey was poverty-stricken and homeless. Look at him today, making $45 million a year and driving the most comfortable cars available.

The Bentley Mulsanne pictured above, however, was a gift he received for his 59th birthday from his wife. Still, it’s a luxury vehicle worth $305K. Well, Harvey gave his wife a Rolls-Royce worth half a million first, but we guess it’s the thought that counts. At 63, Harvey continues to host Steve and Family Feud.