Oprah Winfrey – 1954 Mercedes-Benz 300SL Gullwing, Estimated $605K
According to Forbes, Oprah is worth $2.9 billion, and she’s one of the top ranking self-made women in America. Winfrey is also well-known for being philanthropic. In 2008, she placed three of her classic vehicles for sale with the proceeds intended to go to her charity – The Oprah Winfrey Leadership Academy for Girls in South Africa. It happened during the Monterey Auto Week held at the Pebble Beach Auction. She chose to let go of her 1954 Mercedes-Benz Gullwing as well as her 1997 Aston Martin DB7 and a 1988 Rolls-Royce Corniche. She eventually sold the Benz, which previously belonged to the DuPont family, for $605K.

