popeater.com
He’s got a laundry list of exes and with each romance gone sour, there’s a story that couldn’t be more salacious if it had been scripted. From shooting ex-fiancées to popping out at least one kid with each one of his ex-wives to curing his break-up blues with naked hotel snafus, Charlie Sheen keeps us guessing on his real-life set of Three and a Half Women.
THE PROFIT AND PEELE PARADE
In December of 1984 Charlie welcomed his first child, Cassandra Jade Estevez, with girlfriend, Paula Profit. The two were high school sweethearts, but the lockers and books romance didn’t last long after the birth of their first child when, the following year, Charlie tied the knot with model Donna Peele. But true to Charlie’s track record, the nuptials didn’t seem to stick—especially after Charlie was outed as a client who made more than a few routine visits to Hollywood madam Heidi Fleiss’s establishments. This was our first taste of a long string of highly publicized indiscretions.
KELLY GET YOUR GUN
In 1989, Charlie and girlfriend, actress Kelly Preston, moved in together before Charlie proposed in 1990. That same year, while in their apartment, Charlie accidentally shot Kelly in the arm but thankfully only left a small wound that required two stitches. As with any relationship in which one partner shoots the other, the engagement quickly dissolved leaving Charlie to forge on in his destructive love path.
DENISE RICHARDS: IT’S COMPLICATED
The next contestant in Charlie’s game of love was model and actress Denise Richards. The two met on the 2001 set of Good Advice and married the following year. The couple continued their honeymoon phase for a year before they welcomed their first daughter, Sam, in 2004.
But it was during Denise’s second pregnancy in 2005 that she filed for divorce from the serial Hollywood bad boy. During the legal proceedings, Denise cited that Charlie had made physical and violent threats against her, stored guns under their coffee table and practiced infidelity frequently with prostitutes. In the summer of 2005 their second daughter, Lola, was born.
The Sheen-Richards divorce was a tabloid jackpot as gossip magazines and websites followed the step-by-step proceedings between the the dueling pair. The mud-slinging reached a fever pitch when Denise filed a restraining order Charlie. Although Charlie didn’t appear to stay loyal throughout his first or second marriages, his fans did. Many accused Denise of running a smear campaign against Charlie—the support for the troubled actor downplayed his offenses and put the scrutiny spotlight on ex-wife Denise. The two were officially divorced in November of 2006.
BROOKE AND CHARLIE—ONE IN THE SAME
In 2008, we thought Charlie may have been on the path to recovery when he tied the knot with non-Hollywood girlfriend, Brooke Mueller. Third time seemed to be a charm for Charlie, who welcomed twins, Bob and Max, with her less than a year later. But months later, the dad of five was charged with second-degree when he allegedly attacked her on Christmas and threatened her with a knife. It was the mug shot heard round the world and Charlie was sentenced to a month in rehab and probation stints as well as anger management counseling. Quite certain that things were not going to work out between the estranged couple (shocker!), Charlie filed for divorce from his third wife in November of 2010.
THREE'S A CHARM
Soon enough, Charlie was back to his old tricks, drinking, snorting cocaine and partying with prostitutes, porn stars and other unsavory companions. But, perhaps taking a cue from Hugh Hefner, Charlie settled down with two women, porn star Rachel Oberlin and former nanny Natalie Kenly. The two young women, who he referred to as the "Goddesses" in an interview, quickly became his live-in girlfriends, even taking a part in caring for his twin sons.
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