Bree Olson – 35, $ 5 Million

For some people, Bree Olson’s name is recognized for once living with actor Charlie Sheen. Nevertheless, beauty is more than being the former flame of a Hollywood star. Olson made a name in the adult film industry at the beginning of her acting career, completing 281 films in the industry.

In time, she transitioned to mainstream TV and cinema, appearing in the movies ‘Purgatory Comic,’ ‘Human Centipede 3’ and ‘Power/Rangers.’ Unfortunately, her career move was not very successful, with her last screen appearance being in 2012. The actress has been critical of the adult film industry in the years following her retirement, particularly the stigma attached to being a SMUD movie star.