Charlie Sheen wasn’t always one of Hollywood’s most hated — and the notorious bad boy enjoyed plenty of years as a ladies’ man romancing these big stars and bad girls…
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ASHLEY DUPRÉ: She was the hooker who brought down New York governor Eliot Spitzer — and the King of All Pimps says Ashley Dupré also hooked up with Charlie Sheen. Jason Itzler, a proud purveyor of ladies, claimed that Ashley was just 19 years old when she put on a cheerleader outfit to join Charlie and another hooker for a threesome!
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BREE OLSON: She was already famous as a porn star, but beautiful blonde Bree Olson discovered a whole new world of fame when she became one of Charlie's constant companions — with the star officially naming her as one of his "Goddesses!"
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CAPRI ANDERSON: This beauty proved that you don't have to be a blonde to be a goddess. Charlie brought in porn star Capri as another one of his top gals to share the spotlight!
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CASSANDRA CRUZ: She wasn't around during the "Goddess" years, but this adult actress already had a lot of fans thinking she was out of the world! Cassandra was an official girlfriend of Charlie, who was never ashamed to be seen with X-rated ladies!
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CELESTE STAR: This adult sensation drove Charlie to write epic poetry — and they had a lot to talk about besides just acting! Celeste also directs adult films!
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CHARLOTTE LEWIS: She was a rising star in the '80s, but mainstream actress Charlotte got most of her Hollywood exposure from dating Charlie during his own Hollywood heyday of 1986 through 1988!
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GEORGIA JONES: This adult star joined Capri Anderson as part of Charlie's second duo of live-in beauties — after Bree Olson and Natalie Kenly moved out!
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GIGI RIVERA: This adult actress ended up in the spotlight after she joined other ladies for a wild night with Charlie — that ended up with him begin taken to a hospital in an ambulance!
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JANA JORDAN: This blonde beauty got international exposure after she joined two other X-rated stars to celebrate Charlie's birthday at a restaurant — and cheerfully posed for a photo with Charlie menacing her with a knife!
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KACEY JORDAN: This wild actress almost made different kind of headlines with Charlie — announcing that she became pregnant by Charlie after a condom broke during a 36-hour drug binge. Kacey later had an abortion.
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MELANIE RIOS: This popular porn star was partying with Charlie in the wild hours that would end up with the sitcom star going into rehab in 2011!
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MIA ISABELLA: This transsexual model is known for dating a few rap stars, but reports say that Charlie — who Mia describes as "a very brave person" — also joined her for some hot nights!
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Photo credit: Splash
SCOTTINE ROSS: What's the next step up from Goddess? This X-rated beauty learned after she (briefly) became Charlie's fiancée!
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STACY FUSON: This Playboy model turned a lot of heads when she showed up at Charlie's celebrity roast — and they were rumored to be dating!
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STEPHANIE SEYMOUR: Models don't get more mainstream than this big-name beauty, with Charlie and her dating during his fairly sedate early 1990s.
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SUMMER ALTICE: This Playboy Playmate hooked up with Charlie at a great time in his life. "He was three weeks sober," she recalled, adding: "It was more of a platonic friendship relationship."
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Photo credit: Splash News
TABITHA STEVENS: This big-name X-rated star had a fling with big-name Charlie in the late '90s!
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TAMARA BECKWITH: She's a big reality-television show star in her native England, and the mainstream starlet nearly broke out big in America while dating Charlie!
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WINONA RYDER: They worked together on the 1986 film "Lucas," and the two rising stars went on to date for a while — before heading their very separate ways!
ASHLEY DUPRÉ: She was the hooker who brought down New York governor Eliot Spitzer — and the King of All Pimps says Ashley Dupré also hooked up with Charlie Sheen. Jason Itzler, a proud purveyor of ladies, claimed that Ashley was just 19 years old when she put on a cheerleader outfit to join Charlie and another hooker for a threesome!
Photo credit: Getty Images
BREE OLSON: She was already famous as a porn star, but beautiful blonde Bree Olson discovered a whole new world of fame when she became one of Charlie's constant companions — with the star officially naming her as one of his "Goddesses!"
CAPRI ANDERSON: This beauty proved that you don't have to be a blonde to be a goddess. Charlie brought in porn star Capri as another one of his top gals to share the spotlight!
Photo credit: Splash News
CASSANDRA CRUZ: She wasn't around during the "Goddess" years, but this adult actress already had a lot of fans thinking she was out of the world! Cassandra was an official girlfriend of Charlie, who was never ashamed to be seen with X-rated ladies!
Photo credit: Splash News
CELESTE STAR: This adult sensation drove Charlie to write epic poetry — and they had a lot to talk about besides just acting! Celeste also directs adult films!
Photo credit: Splash News
CHARLOTTE LEWIS: She was a rising star in the '80s, but mainstream actress Charlotte got most of her Hollywood exposure from dating Charlie during his own Hollywood heyday of 1986 through 1988!
GEORGIA JONES: This adult star joined Capri Anderson as part of Charlie's second duo of live-in beauties — after Bree Olson and Natalie Kenly moved out!
Photo credit: Splash News
GIGI RIVERA: This adult actress ended up in the spotlight after she joined other ladies for a wild night with Charlie — that ended up with him begin taken to a hospital in an ambulance!
Photo credit: Splash News
JANA JORDAN: This blonde beauty got international exposure after she joined two other X-rated stars to celebrate Charlie's birthday at a restaurant — and cheerfully posed for a photo with Charlie menacing her with a knife!
Photo credit: Splash News
KACEY JORDAN: This wild actress almost made different kind of headlines with Charlie — announcing that she became pregnant by Charlie after a condom broke during a 36-hour drug binge. Kacey later had an abortion.
Photo credit: Splash News
MELANIE RIOS: This popular porn star was partying with Charlie in the wild hours that would end up with the sitcom star going into rehab in 2011!
Photo credit: Splash News
MIA ISABELLA: This transsexual model is known for dating a few rap stars, but reports say that Charlie — who Mia describes as "a very brave person" — also joined her for some hot nights!
Photo credit: Splash News
SCOTTINE ROSS: What's the next step up from Goddess? This X-rated beauty learned after she (briefly) became Charlie's fiancée!
STACY FUSON: This Playboy model turned a lot of heads when she showed up at Charlie's celebrity roast — and they were rumored to be dating!
STEPHANIE SEYMOUR: Models don't get more mainstream than this big-name beauty, with Charlie and her dating during his fairly sedate early 1990s.
SUMMER ALTICE: This Playboy Playmate hooked up with Charlie at a great time in his life. "He was three weeks sober," she recalled, adding: "It was more of a platonic friendship relationship."
TABITHA STEVENS: This big-name X-rated star had a fling with big-name Charlie in the late '90s!
Photo credit: Splash News
TAMARA BECKWITH: She's a big reality-television show star in her native England, and the mainstream starlet nearly broke out big in America while dating Charlie!
Photo credit: Getty Images
WINONA RYDER: They worked together on the 1986 film "Lucas," and the two rising stars went on to date for a while — before heading their very separate ways!
