Skip to content

Top Navigation

PEOPLE.com PEOPLE.com
    • All News
    • Coronavirus
    • Crime
    • Human Interest
    • Politics
    • Heroes
    • Stories to Make You Smile
    • All Entertainment
    • Celebrity
    • TV
    • Movies
    • Music
    • Country
    • Awards
    • Sports
    • Theater
    • Books
  • Royals
    • All Lifestyle
    • Style
    • Fashion
    • Beauty
    • Health
    • Parents
    • Home
    • Pets
    • Food
    • Tech
    • Travel
  • PeopleTV
    • All Shopping
    • People Tested
    • All Podcasts
    • Me Becoming Mom
    • People Every Day
    • PEOPLE in the '90s

Profile Menu

Join Now

Account

  • Join Now
  • My Profile
  • Email Preferences
  • Newsletters
  • Manage Your Subscription
  • Logout

More

  • Give a Gift Subscription
  • Premium
My Account

Account

  • Join Now
  • My Profile
  • Email Preferences
  • Newsletters
  • Manage Your Subscription
  • Logout

More

  • Give a Gift Subscription
  • Premium
Login
Subscribe

Explore PEOPLE.com

PEOPLE.com PEOPLE.com
  • Explore

    Explore

    • Rita Moreno Says She Dated Elvis as Revenge Against Cheating Ex Marlon Brando: 'It Was Wonderful'

      Rita Moreno Says She Dated Elvis as Revenge Against Cheating Ex Marlon Brando: 'It Was Wonderful'

      Rita Moreno revealed she dated Elvis Presley to get back at her ex-boyfriend Marlon Brando for cheating on her Read More
    • Machine Gun Kelly Poses with Daughter Casie at the 2021 American Music Awards

      Machine Gun Kelly Poses with Daughter Casie at the 2021 American Music Awards

      The American Music Awards, hosted by Cardi B, are broadcasting live from Los Angeles on Sunday Read More
    • Jennifer Lopez Sings from the Heart in New 'On My Way' Music Video

      Jennifer Lopez Sings from the Heart in New 'On My Way' Music Video

      Jennifer Lopez released the official music video for her song "On My Way," which is featured in her upcoming rom-com Marry Me Read More
  • News

    News

    See All News
    Stars Who Opened Up About Their Sexuality and Gender Identity in 2021

    Stars Who Opened Up About Their Sexuality and Gender Identity in 2021

    • Coronavirus
    • Crime
    • Human Interest
    • Politics
    • Heroes
    • Stories to Make You Smile
  • Entertainment

    Entertainment

    See All Entertainment
    The Best (& Worst) Jeopardy! Celebrity Guest Host Show Moments

    The Best (& Worst) Jeopardy! Celebrity Guest Host Show Moments

    • Celebrity
    • TV
    • Movies
    • Music
    • Country
    • Awards
    • Sports
    • Theater
    • Books
  • Royals
  • Lifestyle

    Lifestyle

    See All Lifestyle
    Billie Eilish Ditches Her Blonde Hair for Brunette Tresses: 'Miss Me?'

    Billie Eilish Ditches Her Blonde Hair for Brunette Tresses: 'Miss Me?'

    The singer revealed that she dyed her hair dark brown after debuting her blonde look earlier this year
    • Style
    • Fashion
    • Beauty
    • Health
    • Parents
    • Home
    • Pets
    • Food
    • Tech
    • Travel
  • PeopleTV
  • Shopping

    Shopping

    See All Shopping
    • People Tested
  • Podcasts

    Podcasts

    See All Podcasts
    Sen. Tammy Duckworth Calls Going Back to Work After Having a Miscarriage 'Inhumane'

    Sen. Tammy Duckworth Calls Going Back to Work After Having a Miscarriage 'Inhumane'

    "Even though we cleared my calendar for the day, I was still on the phone. There was no resting, you just kept on going," Tammy Duckworth says on an episode of PEOPLE's podcast Me Becoming Mom
    • Me Becoming Mom
    • People Every Day
    • PEOPLE in the '90s

Profile Menu

Subscribe this link opens in a new tab
Join Now

Account

  • Join Now
  • My Profile
  • Email Preferences
  • Newsletters
  • Manage Your Subscription
  • Logout

More

  • Give a Gift Subscription
  • Premium
My Account

Account

  • Join Now
  • My Profile
  • Email Preferences
  • Newsletters
  • Manage Your Subscription
  • Logout

More

  • Give a Gift Subscription
  • Premium
Login
Sweepstakes

Follow Us

  1. People.com
  2. Celebrity
  3. Charlie Sheen's Former 'Goddesses'

Charlie Sheen's Former 'Goddesses'

Before he fell for Rachel Oberlin and Natalie Kenly, meet the women – Kelly Preston! Stephanie Seymour! Denise Richards! – who held the key to Sheen's heart
By Kiran Hefa Updated March 02, 2011 04:00 PM
Skip gallery slides
FB Tweet

1 of 7

FB Tweet
Pinterest Email Send Text Message

KELLY PRESTON

KELLY PRESTON
Credit: Ron Galella, Ltd./WireImage

Dated in: 1990
The short-lived romance between Preston and Sheen, which saw the couple get engaged, was marked by a bizarre incident in which Preston was accidentally shot by a loaded gun Sheen left in the pocket of his pants on a bathroom floor. Shortly after their split in March, Preston went on to wed John Travolta.

1 of 7

Advertisement
Advertisement

2 of 7

FB Tweet
Pinterest Email Send Text Message

GINGER LYNN ALLEN

GINGER LYNN ALLEN
Credit: Judie Burstein/Globe

Dated from: 1990 – 1995
After splitting with Preston, Sheen moved on with adult film actress Allen, whom he dated on-and-off for five years. "When Charlie's sober, he's sweet, kind, loving, generous," she told PEOPLE. "When he's drinking and using, he's out of control."

2 of 7

3 of 7

FB Tweet
Pinterest Email Send Text Message

STEPHANIE SEYMOUR

STEPHANIE SEYMOUR
Credit: Marion Curtis/DMI/Time Life Pictures/Getty; Rex USA

Dated in: 1992
The stunning supermodel was romanced by Sheen in the midst of her two-year relationship with Guns N' Roses frontman Axl Rose. "We're madly in love and very happy together," Sheen gushed in June 1992, a year before Seymour and Rose officially called it quits.

3 of 7

Advertisement
Continued on next slide.
Advertisement

4 of 7

FB Tweet
Pinterest Email Send Text Message

HEIDI FLEISS'S GIRLS

HEIDI FLEISS'S GIRLS
Credit: David Keeler/Liaison/Getty; Ron Galella, Ltd./WireImage

Dated from: 1991 – 1993
When Hollywood's madam to the stars was brought down for tax evasion in 1995, Sheen served as the star witness in her trial, admitting he had spent $53,000 on 11 of Fleiss's prostitutes. For her part, Fleiss praised Sheen to Vanity Fair, saying, "Charlie was a gentleman. [At his parties,] he'd pay for all his friends."

4 of 7

Advertisement

5 of 7

FB Tweet
Pinterest Email Send Text Message

BRITTANY ASHLAND

BRITTANY ASHLAND
Credit: Chris Pizzello/AP (2)

Dated in: 1996
The tumultuous relationship between Sheen and Ashland ended in a June 1997 courtroom when Sheen pleaded no contest to charges of battery, with Ashland accusing her ex of throwing her onto the kitchen floor of his San Fernando Valley home and splitting her lip during a December 1996 argument. "I hope that for his good and everybody else's, he decides to change his behavior," Ashland told the court through attorney Gloria Allred.

5 of 7

6 of 7

FB Tweet
Pinterest Email Send Text Message

DENISE & CHARLIE

DENISE RICHARDS
Credit: Miranda Shen/Globe

Reports of Sheen relapsing and making chilling death threats led to wife Richards, who was pregnant with Sheen's child, filing for divorce in 2005.

6 of 7

Advertisement
Advertisement
Continued on next slide.
Advertisement

7 of 7

FB Tweet
Pinterest Email Send Text Message

BROOKE MUELLER

BROOKE MUELLER
Credit: Gregg DeGuire/WireImage

Married from: 2008 – present, divorce pending
Sheen and real estate investor Mueller made it official on May 30, 2008, tying the knot in an intimate L.A. ceremony, and becoming a family a year later with the birth of their twin boys. But on Christmas Day 2009, the Two and a Half Men star was arrested for domestic violence, and soon checked himself into rehab alongside his wife. Though Mueller said she hoped to save their marriage, the couple ultimately filed for divorce in November 2010 after months of living apart.

7 of 7

Advertisement
Advertisement
Replay gallery

Share the Gallery

Pinterest Facebook

Up Next

By Kiran Hefa

    Share the Gallery

    Pinterest Facebook
    Trending Videos
    Advertisement
    Skip slide summaries

    Everything in This Slideshow

    Advertisement

    View All

    1 of 7 KELLY PRESTON
    2 of 7 GINGER LYNN ALLEN
    3 of 7 STEPHANIE SEYMOUR
    4 of 7 HEIDI FLEISS'S GIRLS
    5 of 7 BRITTANY ASHLAND
    6 of 7 DENISE & CHARLIE
    7 of 7 BROOKE MUELLER

    Share & More

    Pinterest Email Send Text Message
    PEOPLE.com

    Magazines & More

    Learn More

    • Subscribe this link opens in a new tab
    • Advertise this link opens in a new tab
    • Content Licensing
    • Accolades this link opens in a new tab

    Connect

    Follow Us
    Subscribe to Our Newsletter
    Meredith© Copyright 2022 Meredith Corporationthis link opens in a new tab. People is a registered trademark of Meredith Corporation All Rights Reserved. People may receive compensation for some links to products and services on this website. Offers may be subject to change without notice. Privacy Policythis link opens in a new tab Terms of Servicethis link opens in a new tab Ad Choicesthis link opens in a new tab Manage Push Notificationsthis link opens in a new tab California Do Not Sellthis link opens a modal window Web Accessibilitythis link opens in a new tab

    Manage Push Notifications

    If you would like to opt out of browser push notifications, please refer to the following instructions specific to your device and browser: Google Chrome and Android, Firefox, Safari, or Microsoft Edge.
    © Copyright PEOPLE.com. All rights reserved. Printed from https://people.com

    Sign in

    View image

    Charlie Sheen's Former 'Goddesses'
    this link is to an external site that may or may not meet accessibility guidelines.