Charlie Sheen’s friends may refer to him fondly as The Machine for his impressive partying stamina, but with the recent announcement that he will wed porn star Brett Rossi, perhaps the nickname should also be applied to his growing list of wedding ceremonies. The Anger Management lead gave an exclusive tip to People that he intended to tie the knot with Rossi, and apparently even played the part of an old-fashioned gentleman by getting down on one knee to propose as the two spent a charming Valentine’s weekend in Hawaii.
When this newest marital arrangement becomes sealed legally, Sheen’s list of wives may start to resemble his film bio in length. While the oft-beleaguered star may not count his first marriage–to model Donna Peele in 1995–as legitimate due to the fact it was annulled, it happened nonetheless, making Rossi the fourth Mrs. Charlie Sheen to date. Were it not for an alleged accidental shooting of his then-fiance Kelly Preston in 1990, Rossi might have even been the fifth instead. To be fair, both Sheen and Preston have since claimed the accident had nothing to do with him or their eventual parting, but the endless speculation possibilities are uniquely fascinating regardless.
The newly engaged pair could not be happier with this development. Rossi gushed to E! about the ring, calling it both classic and beautiful, and was apparently blown away by the proposal. After spending a charming Valentine’s Day together, the couple watched the sun rise the next morning, and it was then that Sheen popped the question. Rossi was, in her own words, not expecting this at all. She also went on to say that neither person has ever been happier, and that Sheen is her soul mate and best friend.
For her sake, this praise had better hold true over time, as Sheen’s track record is not especially flattering; he is a wedding machine, after all. Once his marriage with Peele was annulled in 1996, Sheen reportedly spent the rest of the decade dating adult film industry stars, something he clearly still has a fondness for today. He chose to settle down once again in 2002, this time with actress Denise Richards. The couple would go on to have two children together, although Richards filed for divorce while still pregnant with the second in 2005. The divorce became official in 2006.
Next in line was actress Brooke Mueller in 2008, who gave birth to Sheen’s twin boys, Bob and Max. This marriage ended in 2011 accompanied by a restraining order from Mueller against Sheen, who she reportedly asserted was “currently insane” in the document. After being linked to several more adult film star actresses in the divorce aftermath, Sheen then met Rossi.
Sheen’s turbulent lifestyle and various struggles have not been easy to miss over the years, but looking on the bright side, maybe all he needed was the right girl–for real, this time. If Rossi and Sheen are truly the soul mates she hopes they are, Sheen may no longer be referred to as the machine, either for his hard-partying ways or his undiagnosed addiction to marriage proposals.
By Spencer Hendricks