Skip to content

Top Navigation

PEOPLE.com PEOPLE.com
  • News
    • Coronavirus
    • Crime
    • Human Interest
    • Politics
  • Entertainment
    • Celebrity
    • TV
    • Movies
    • Music
    • Country
    • Awards
    • Sports
    • Theater
    • Books
  • Coronavirus
  • Royals
  • Lifestyle
    • Style
    • Fashion
    • Beauty
    • Health
    • Parents
    • Home
    • Real Estate
    • Pets
    • Food
    • Shopping
    • Tech
  • PeopleTV
  • Shopping
    • Coupons

Profile Menu

Your Account

Account

  • Join Now
  • Email Preferences
  • Newsletters
  • Manage Your Subscription

More

  • Give a Gift Subscription
  • Premium
Login
Logout
Subscribe

Explore PEOPLE.com

PEOPLE.com PEOPLE.com
  • Explore

    Explore

    • Every Tiara Worn at a Royal Wedding

      From Princess Beatrice to Meghan Markle Read More Next
    • Engineer Creates App To Translate Your Cat

      Find out what your cat is trying to tell you with a new cat app Read More Next
    • The Sweetest Photos of Princes Harry with Diana

      Princess Diana died when Harry was just 12 years old Read More Next
  • News

    News

    See All News

    Sean Connery's Cause of Death Revealed Weeks After He Dies at Age 90

    Sean Connery died on Oct. 31 at age 90
    • Coronavirus
    • Crime
    • Human Interest
    • Politics
  • Entertainment

    Entertainment

    See All Entertainment

    Coyote Ugly Turns 20: Where Is the Cast Now?

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

    Lifestyle

    See All Lifestyle

    Introducing ... PEOPLE's Products Worth the Hype

    • Style
    • Fashion
    • Beauty
    • Health
    • Parents
    • Home
    • Real Estate
    • Pets
    • Food
    • Shopping
    • Tech
  • PeopleTV
  • Shopping

    Shopping

    • Coupons

Profile Menu

Subscribe this link opens in a new tab
Your Account

Account

  • Join Now
  • Email Preferences
  • Newsletters
  • Manage Your Subscription

More

  • Give a Gift Subscription
  • Premium
Login
Logout
Sweepstakes

Follow Us

People is on Community!
Text us for exclusive photos and videos, royal news, and way more.
Text: 212-479-1704
  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 Mail Email iphone Send Text Message

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 Mail Email iphone Send Text Message

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 Mail Email iphone Send Text Message

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 Mail Email iphone Send Text Message

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 Mail Email iphone Send Text Message

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 Mail Email iphone Send Text Message

DENISE & CHARLIE

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 Mail Email iphone Send Text Message

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 options

Pinterest Mail Email iphone Send Text Message

Login

PEOPLE.com

Magazines & More

Learn More

  • Subscribe this link opens in a new tab
  • Advertise
  • Content Licensing
  • Sitemap
  • Student Offer this link opens in a new tab

Connect

People is on Community!
Text us for exclusive photos and videos, royal news, and way more.
Text: 212-479-1704
Newsletter Sign Up
Other Meredith Sites

Other Meredith Sites

  • 4 Your Health this link opens in a new tab
  • Allrecipes this link opens in a new tab
  • All People Quilt this link opens in a new tab
  • Better Homes & Gardens this link opens in a new tab
  • Bizrate Insights this link opens in a new tab
  • Bizrate Surveys this link opens in a new tab
  • Cooking Light this link opens in a new tab
  • Daily Paws this link opens in a new tab
  • EatingWell this link opens in a new tab
  • Eat This, Not That this link opens in a new tab
  • Entertainment Weekly this link opens in a new tab
  • Food & Wine this link opens in a new tab
  • Health this link opens in a new tab
  • Hello Giggles this link opens in a new tab
  • Instyle this link opens in a new tab
  • Martha Stewart this link opens in a new tab
  • Midwest Living this link opens in a new tab
  • More this link opens in a new tab
  • MyRecipes this link opens in a new tab
  • MyWedding this link opens in a new tab
  • My Food and Family this link opens in a new tab
  • MyLife this link opens in a new tab
  • Parenting this link opens in a new tab
  • Parents this link opens in a new tab
  • People en Español this link opens in a new tab
  • Rachael Ray Magazine this link opens in a new tab
  • Real Simple this link opens in a new tab
  • Ser Padres this link opens in a new tab
  • Shape this link opens in a new tab
  • Siempre Mujer this link opens in a new tab
  • Southern Living this link opens in a new tab
  • SwearBy this link opens in a new tab
  • Travel & Leisure this link opens in a new tab
© Copyright 2021 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 . All rights reserved. Printed from https://people.com

View image

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