Steven Tyler | Total Amount: At least $ 5.771 million

The band leader of Aerosmith, Steven Tyler, sure found fame starting the ‘70s. His band was behind several hit albums like Rocks and Toys in the Attic. They also released singles that made everyone crazy such as Sweet Emotion and Walk This Way. Since the ‘80s, Tyler has been involved in solo endeavors, which were met with mixed success.

While Tyler had a generally profitable career, it appeared that he did not have good money management skills. He had personal struggles that led him to make bad financial decisions. For some parts, though, he made the decision, such as by purchasing a list of real estate properties, one of which is a $4.8 million home in Hawaii. Every time he is stressed and needed privacy, he would head over to this vacation spot. Tyler also has several high-end luxury cars, such as a Porsche Turbo and a Hennessey Venom GT Spyder.