29.Jessica Simpson

Ever since she was a kid, Jessica Simpson had set her sights on life as a successful singer. A few years later, her dream came true and even brought the singer to other ventures. Besides releasing one album after another, Jessica Simpson also received fame for her role in the film Dukes of Hazzard. She was also able to make investments in the fashion business with her Jessica Simpson Collection clothing line.

With Jessica Simpson succeeding in her many endeavors — as a singer, author, actress, and businesswoman — it’s safe to say that she has earned more than enough to reward herself with something nice. Among the things the singer bought over the years are her two houses and her cars. Her cars include a Cadillac Escalade, a Range Rover, and a Bentley Continental GTC Mulliner.