Charlie Sheen: The complete hookup history

Douglas Charles Managing Editor

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This week in alleged sexual history I thought we’d take a look at the life and times of one Charlie Sheen since he was back in the news recently. Chuck is easily as prolific as a couple of the other men we’ve featured but his story has a twist as a majority of the women he’s been with seem to make a living doing the deed (they’re porn stars, in case you didn’t get that reference). Let’s see if I can find enough SFW pics to do this chronology justice (and how many names you recognize).

Robin Wright (1981-1982)

Charlie wasn’t always into porn stars. He dated the future ex-Mrs. Sean Penn a couple of years before she hit it big on Santa Barbara.

Winona Ryder (1986)

Once again, Chuck was ahead of the curve, dating Ryder before she came to the nation’s attention in Heathers in 1988 as both actors appeared in the film Lucas right around this time.

Kelly Preston (1987-1990)

Preston and Sheen were briefly engaged. Then he shot her in the arm (accidentally) and that was pretty much the end of that relationship.

Cathy St. George (1988-1989)

Charlie’s first short foray into the world of “adult” stars, St. George was a Playmate of the Month in August 1982.

Tracy Richman (1989-1991)

Chuck got to her a year before Jack Nicholson did. Later she appeared on the Charlie Sheen E! True Hollywood Story, which is pretty much her most prestigious acting credit.

Ginger Lynn Allen (1990-1996)

Sheen finally found what he likes, and as we all know Charlie likes him some porn stars. Member of the AVN Hall of Fame.

Stephanie Seymour (1992)

Back to a non-adult film star, but a woman who, thanks to her job as a model, he had more than likely already seen topless before they’d met.

Heather Hunter (1994)

Inducted into the AVN Hall of Fame in 2003.

Donna Peele (1995-1996)

For some reason, Peele, a model, married Sheen. Naturally, he announced the engagement while on the stand during the Heidi Fleiss trial. The marriage did not last long.

Brittany Ashland (1996-1997)

At some point during this relationship she allegedly attacked him with a fork. She also sued him for allegedly physically abusing her.

Tabitha Stevens (1997)

Inducted into the AVN Hall of Fame in 2007.

Summer Altice (1999-2000)

Playmate of the Month in August of 2000.

Denise Richards (2001-2006)

I think we all know how this one ended.

Brooke Mueller (2006-2009)

And this one.

Capri Anderson (2010)

Remember when Charlie was found drunk, naked, and with an escort locked in his hotel room closet? That woman was Capri.

Kacey Jordan (2011)

Sheen allegedly paid her $30,000 to spend two days with him.

Bree Olson & Natalie Kenly (2011)

His Goddesses.

Other less-substantiated alleged flings…

Cathy Barry, Tamara Beckwith, Ashley Dupré, Heidi Fleiss, Stacy Fuson, Chloe Jones, Melanie Rios, Dominique Simone, Teri Starr, Natasha Terry

Photo credit: YouTube/FX