Dolly Parton – $39.9K, 1997 Cadillac D’Elegance
From living in a one-room cabin with a family of farmers to winning 11 Grammy Awards, Dolly Parton epitomizes what it means to go from grass to grace. The country singer’s achievements and talents are so vast that she was officially titled a Living Legend by the Library of Congress in 2004.
She didn’t forget her humble beginnings, as she is said to have purchased several luxuries for her parents. This includes the 1997 Cadillac D’Elegance, priced at the original retail price of $39,995. The rumor is she bought the car for her mom. She put it on display in a museum in 2009, six years after her mom passed.