Whatever your thoughts are about Charlie Sheen, there is no denying his playboy reputation. Rising to fame in the 80s, the son of Martin Sheen has led a very public, and at times controversial life. Films such as Wall Street, Young Guns, and Major Leauge turned him into one of Hollywood’s leading men and an in-demand actor. But his penchant for the party life soon found the actor in trouble. Substance abuse problems impacted his career and Sheen hit rock bottom during the 90s. But one thing remained consistent: the frequency of Charlie Sheen’s girlfriends.

No matter how bad life was going, New York born Sheen always managed to have a beautiful woman on his arm. He has been married three times, has a fondness for ladies of the night, and has talked about being a sex addict in the past. His harem of lovers only grew when he had a comeback with the hit series Two and a Half Men. At one point he was involved in a consensual relationship with two women at the same time. Even after the announcement that he was HIV positive and that interview where he mentions having tiger blood and winning at life, Sheen has had the women flocking after him. 

While certainly a good-looking fella, Sheen must have some sort of it factor. Or maybe it’s the money? Whatever the case, Sheen is a charming gent with a long history of bedding attractive women. To highlight the party animal’s long list of lovers, here is a guide to Charlie Sheen’s girlfriends over the years.

1. Scottine Ross

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You will quickly discover Charlie Sheen has a type. Not in regards to looks or personality, but their job. He is a big fan of adult film actresses. Scottine Ross, stage name Brett Rossi, is a model turned pornographic star who dated Sheen for almost a year from November 2013 to October 2014. Sheen met Ross after watching her videos and deciding he had to date her. After pursuing her to no avail, he offered Ross $10,000 for a date. Ross relented and went on a date with Sheen. It must have gone well as the two fell in love, got engaged, and planned to marry, but Sheen called things off a month before the nuptials were to take place.