Charlie is an alcoholic, excessive gambler and womanizer…oh wait, this list is about the character Charlie Harper not the actor Charlie Sheen. Charlie Harper is an alcoholic, excessive gambler and womanizer. Charlie Harper, played by Charlie Sheen, was the protagonist of the hit CBS sitcom, Two and a Half Men. Both the character and actor seem to have a lot in common. They’re both rich, seem to put in little effort and have brothers that everyone forgets about. Both are also very successful in their careers and have dated some of the most beautiful women. Charlie Sheen is the son of Martin Sheen and the brother of Emilio Estevez. He’s starred in a number of classic films including, Platoon, Wall Street and Major League. His character, Charlie Harper, made millions writing jingles for commercials and was also a children’s entertainer, Charlie Waffles. The character has a fear of commitment and goes through women like Charlie Sheen goes through…well, women. The character was famously killed off after Charlie Sheen had a very public falling out with the creator of the series, Chuck Lorre. Throughout his time on the series, his character dated several women. Here is a look at 15 of the hottest girlfriends and one night stands of Charlie Harper.
15) Michelle – Liz Vassey
Michelle, played by Liz Vassey, was a dermatologist that dated Charlie. They met in one of the most adorable ways possible. She removed a mole from his butt. Well, maybe it’s not that adorable. They dated for a while but Charlie got turned off when he found out that she was older than him.
14) Rose – Melanie Lynskey
The innocent looking but possibly deeply disturbed Rose, could be considered both Charlie’s greatest love and villain. Prior to the start of the show, the two have a one night stand. After, Rose begins to stalk Charlie. Rose wants to be with Charlie and only Charlie. Later, Charlie realizes he has feelings for her but they go in and out of each other’s lives for a few seasons. Eventually, Charlie wants to be with Rose and only Rose too. He proposes and they go to Paris. While in Paris, Rose catches Charlie with another women in the shower. Later, he is mysteriously pushed in front of the very train that kills him. At his funeral, several of the other women suspect that Rose had something to do with his death.
13) Jenna Elfman
The beautiful Jenna Elfman played the wild and crazy Frankie, in episodes 15 and 16 from season 1. Charlie and Alan meet Frankie when they find her smashing the windows of a BMW in a parking lot. Because Charlie has a crush on Frankie (and she tells him that she has no where to go), Charlie invites her to stay at his place. Unfortunately for Charlie, Frankie tells him that she doesn’t have any interest in sleeping with him, and ends up kissing Alan instead.
12) Chelsea Melini – Jennifer Bini Taylor
Charlie Harper has had many one night stands and girlfriends, but Chelsea was the first one he confessed his love for, without her having to say it first. Well, it may have been by accident but still he said it. Chelsea was a one night stand but it turned into more and eventually, they got engaged. However, things didn’t work out for them. Charlie did leave her with a parting gift, at his funeral she reveals that he gave her a STD.
11) Isabella- Jodi Lyn O’Keefe
Jodi Lyn O’Keefe played the sexy, yet somewhat twisted, Isabella. She was a Satanist and a part of an occult, which are the very reasons Charlie wanted to date her. Well, more like sleep with her but it’s all the same to Charlie. She may have even put a curse on him. She attends his funeral where she reveals that Charlie gave her herpes. Seems like he cursed her in the end.
10) Judge Linda Harris – Ming-Na Wen
Judge Linda Harris, Ming-Na Wen, first met Charlie Harper when they were set up on a double date by Alan. Initially, she is disgusted by him but he eventually wins her over with his charm. Actually, he gets drunk and ends up in court with her as the judge, but that can be charming too. She is one of the few women that makes him wait to have sex.
9) Melissa – Kelly Stables
Melissa, played by Kelly Stables, was the beautiful and charming receptionist who worked for Alan. Eventually, she starts to date Charlie. After a terrible and horrible end to their relationship, she starts to develop feelings for Alan.
8) Sherri – Jeri Ryan
Charlie Harper himself stated that the gorgeous Sherri, played by Jeri Ryan, was the female version of himself. That’s a pretty big statement. Sherri used Charlie for sex and it would have been okay but she used Charlie. Charlie is used to being the one to do the using. Later, she dates Charlie’s brother Alan, played by Jon Cryer. Jeri Ryan has appeared on Star Trek: Voyager, Boston Public and Dark Skies.
7) Kandi- April Bowlby
The sexy and gorgeous Kandi, played by April Bowlby, was the dim witted girlfriend of Charlie Harper. She was a recurring character is season 3, a regular in season 4 and guest starred in season 10. She is initially Charlie’s girlfriend but he dumps her for Mia. She eventually begins to date Charlie’s brother Alan.
6) Mia Adams – Emmanuelle Vaugier
Mia Adams wasn’t just a beautiful and breathingtaking one night stand that Charlie Harper had. She was much more than that. He may have actually loved her. She was a ballet teacher and in order to get close to her, he makes his nephew Jake, played by Angus T. Jones, take lessons. Eventually, they become engaged, that’s right, the man that could never commit finally did. She was even able to convince him to give up cigars, meat and alcohol. Well, kind of, he was actually doing all the stuff in secret and behind her back. They almost get married but break it off at the last minute.
5) Sissy “Didi’ – Jud Tylor
The gorgeous, stunning and stereotypical blonde Sissy “Didi”, played by Jud Tylor, was one of the many one night stands that Charlie regretted immediately. He breaks off his relationship with her because he feels she is “too dumb”.
4) Courtney Leopold – Jenny McCarthy
Jenny McCarthy played the sexy and seductive, Courtney Leopold, a.k.a Sylvia Fishman. Courtney was a con-artist that was just trying to con Charlie out of all of his money. Instead, she got his heart and all of his money. She appeared in season 5, 8 and 9. Jenny McCarthy is a well known celebrity who has appeared on The Drew Carey Show, Wings and Just Shoot Me. She also had her own short lived sketch show, The Jenny McCarthy Show and a sitcom, Jenny. She rose to fame appearing in Playboy and was eventually named Playmate of the Year.
3) Liz – Teri Hatcher
Liz, played by the beautiful Teri Hatcher, was the sister of Alan’s ex-wife Judith. Charlie and Liz hook up at Alan and Judith’s wedding but she claims she doesn’t remember. Which makes no sense because Charlie does remember and that never happens. Teri Hatcher is a well known celebrity and is best known for her role on the hit ABC drama, Desperate Housewives.
2) Laura Lang – Heather Locklear
The beautiful, sexy and tough divorce attorney Laura Lang, played by Heather Locklear, was hired by Alan for his divorce proceedings. Of course, Charlie screws everything up by sleeping with her. She wanted Charlie for sex whenever she wanted and when he refused, Alan was the one to suffer. Heather Locklear is considered a sex symbol of the 90’s. She is well known for her roles on the hit series, Dynasty, Melrose Place and Spin City. She remains one of the most beautiful actresses in Hollywood.
1) Lisa – Denise Richards
The beautiful and stunning Lisa, played by Denise Richards, is the former girlfriend of Charlie Harper. Despite having deep, strong feelings for her and being extremely attracted to her, he had a difficult time committing to a relationship. She appeared in the season one episode, “Merry Thanksgiving” and again in season two, “Yes, Monsignor”. Denise Richards is also the ex-wife of Charlie Sheen and they have two daughters together. She has appeared in a number of films, such as, Starship Troopers, Wild Things and Madea’s Witness Protection. She’s also appeared in magazines, including FHM, Maxim and Men’s Health. She appeared in Playboy four months after giving birth to her first child. Her and Charlie Sheen are now on good terms after divorcing. She has guest starred in his new show on FX, Anger Management. She remains one of the most beautiful women to date both Charlie Harper and Charlie Sheen.