• Tamara Beckwith (1980)

  • Robin Wright Penn (1981 - 1982 )

  • Paula Profitt (1984 - 1986)

    Pictured is Sheen’s daughter, Cassandra Jade Estevez, from his relationship with Paula Profit.

  • Dolly Fox (1986)

  • Winona Ryder (1986)

  • Valerie Barnes (1986)

  • Heidi Fleiss (1988)

  • Cathy St. George (1988 - 1989)

  • Tracy Richman (1989)

  • Kelly Preston (1989 - 1990)

  • Dominique Simone (1990 )

  • Ginger Lynn (1990 - 1992)

  • Stephanie Seymour (1992)

  • Heather Hunter (1993)

  • Donna Peele (married) (1995 - 1996)

  • Chloe Jones (1996)

  • Brittany Ashland (1997)

  • Tara Phillips (1997)

  • Teri Starr (1999)

  • Sky Valencia (1999)

  • Charlese LaMour (1999)

  • Stacy Fuson (1999)

  • Summer Altice (1999- 2000)

  • Margaret Schinke (2000 - 2001)

  • Denise Richards (married) (2001 - 2006)

  • Brooke Mueller (Married) (2006-2010)

  • Kacey Jordan (2011)

  • Rachel Oberlin a.k.a Bree Olson (2011)

  • Natalie Kenly (2011)