Charlie has undoubtedly earned the title of “Playboy with a Capital P.” Sheen’s acting chops in Two and a half men and Wall Street showcased his talent, but it was his storied personal life that cemented his legacy as one of Hollywood’s most notorious playboys.
Over the years, Sheen has been romantically linked with a series of high-profile adult film stars, adding to his reputation as Hollywood’s most eligible—and elusive—bachelor. In 2010, he dated Melanie Rios, drawing media fascination.
The following year saw his connection to American pornstar Kacey Jordan, whose stories of partying with Sheen dominated headlines.
In 2013, he was linked with Celeste Star, and by 2014, Sheen had moved on to a turbulent relationship with Brett Rossi
(Tryst Agency), an adult film star he initially planned to marry before their relationship ultimately ended.
Reports estimate that Sheen has dated and has encounters with close to
5,000 women. Each relationship seemed to amplify his mystique, transforming him into a larger-than-life figure who thrived on the limelight.
Here’s a comprehensive overview of Charlie Sheen’s romantic relationships:
1. Robin Wright (1981–1982)
2. Paula Profitt (1984–1986)
3. Dolly Fox (1985–1987)
4. Charlotte Lewis (1986–1988)
5. Winona Ryder (1986)
6. Cari Haim (1986)
7. Valerie Barnes (1986)
8. Kelly Preston (Engaged in 1990)
9. Ginger Lynn (1990–1996)
10. Dominique Simone (1990)
11. Cathy St. George (1988–1989)
12. Tracy Richman (1989)
13. Heidi Fleiss (1988)
14. Stephanie Seymour (1992–1994)
15. Shauna O’Brien (1992)
16. Donna Peele (Married 1995–1996)
17. Chloe Jones (1995–1996)
18. Brittany Ashland (1996–1997)
19. Tabitha Stevens (1997)
20. Tara Phillips (1997)
21. Charlese LaMour (1999)
22. Stacy Fuson (1999)
23. Sky Valencia (1999)
24. Summer Altice (1999–2000)
25. Margaret Judge (2000–2001)
26. Denise Richards (Married 2002–2006)
27. Izabel Goulart (2006)
28. Brooke Mueller (Married 2008–2011)
29. Capri Anderson (2010)
30. Melanie Rios (2010)
31. Kacey Jordan (2011)
32. Natalie Kenly (2011)
33. Bree Olson (2011)
34. Georgia Jones (2012–2013)
35. Jayme Langford (2013)
36. Celeste Star (2013)
37. Jana Jordan (2013)
38. Brett Rossi
(Tryst Agency) (Engaged in 2014)
39. Amanda Lauren Bruce (2015)
40. Jessica Impiazzi (2016)
