Don’t even pretend that you never watched Two and a Half Men. Sure, maybe the series wasn’t exactly wildly popular when it first came on: it’s premise about a divorcee moving in with his Playboy brother and lugging his half-owned kid along with him seemed a bit boring and akin to Neil Simon comedies that were predictable and slapstick. Adding to it were the facts that the show was led by Jon Cryer, a great actor in both comedy and drama, and Charlie Sheen, a man who had once proven his acting ability but had since resigned to cashing his checks with as little effort as possible. Sure, Charlie Sheen (playing the character Charlie Harper) was entertaining at times, but most of this is due to the fact that he was essentially playing a different version of himself. And once he got swept away in all of the drugs and addiction problems, his uprooted sanity caused viewers to flock to the show, even if just to watch him unravel on screen.
Here’s the thing: there was once an admirable version of Charlie Sheen. Remember when he was in Platoon? That Charlie is practically unrecognizable to the mess of a human being he’s become today! Nowadays, he’s a balding, flabby but twiggy, lazy, grumpy mess of a man, and producers on Two and a Half Men thought they could disguise all that by combing up his hair, throwing a bowling shirt on him, and pretending he plays a rich man? Nope. We’re not buying it. His character had gaggles of sexy, brilliant, gorgeous, talented women that were excited to vie for his attention and manhood when, in reality, no one in their right mind would want to attach themselves to that.
There are plenty of women who deserved better than Charlie Sheen and were stuck with Charlie Harper on the show. Here are 15 babes from the show who are way too hot to be stuck with Charlie Sheen:
15. Jenny McCarthy, aka Courtney Leopold
Do we even have to talk more about this? Most of you all know who Jenny McCarthy is, though probably not at all from her time on Two and a Half Men. Jenny has had probably the most success in her career by way of modeling (for Playboy and the like), though she’s also been in some movies and television shows to bolster her success, like Scary Movie 3 and Return of the Mac. On the show, she played Courtney Leopold: a girlfriend of Charlie’s that was on again-off again throughout season five. She was also known, however, as Sylvia Fishman- and her main hustle was hustling! She was quite a good con-artist, one that was able to take advantage of Charlie quite well (in more ways than one). However, would this con artist have had any interest in Charlie if he didn’t have money? We are quite certain not.
14. April Bowlby, aka Kandi
KANDI! If you remember no other women on this list, you’ve got to remember Kandi! Not only was she without a doubt one of the sexiest ladies that ever came upon the show, but she had a long running contract with the show that lasted a couple of seasons. She first met and hooked up with Charlie; however, when Charlie doesn’t return her calls and starts dating someone else, Kandi confronts Alan on it and finds a lot of comfort in his arms. The two end up getting married, though of course that doesn’t end well either. Kandi was so dumb at times, but stunningly gorgeous- it was no wonder that Alan fell so hard, so fast for her. She eventually did very well in her acting career and dumped Alan for a variety of reasons, though can you blame her? While we’re not here to dump on Alan, he’s not exactly a prize pig either. Kandi obviously could have done much better than either of the Harper boys.
13. Jennifer Bini Taylor, aka Chelsea Melini
Even if you watched a rare episode as it came on in reruns, you probably remember Chelsea. Not only was she an absolute stunner, but she was in so many episodes (especially in Charlie’s final days on the show) that it was hard to find an episode she wasn’t in for a while. Chelsea, played by the voluptuous Jennifer Bini Taylor, was a romantic interest of Charlie’s that evolved from one-night-stand to life partner. After admitting he loved her too early in the relationship, he stubbornly tries to make her say it too- going so far as to propose and get engaged. However, things didn’t work out and Chelsea became wiser: she runs off with Alan’s attorney and only has sporadic encounters with Charlie in the future. But let’s be real, why would Chelsea stick around for Charlie? Not only would she be settling in every way possible, but the relationship built on poor planning was doomed to fail anyways.
12. Jenna Elfman, aka Frankie
Here’s a character that might have actually been reckless enough to stay with Charlie. Jenna Elfman played Frankie in Two and a Half Men, a character Charlie stumbles upon as she’s vandalizing her shrink’s car. The two proceed to develop an attraction towards each other that is nothing but unhealthy for the both of them, since they’re both mentally unstable with addiction problems and tendencies towards self-destruction. She toys with Alan and Charlie’s emotions for a little while, so all of us were left wondering by the time she ditched the guys, “did she ever really have a thing for them?” Our best guess is that probably, no- she did not. We’re willing to bet that Frankie was reaching the pinnacle of her downward spiral and she needed someone, ANYONE, to cling to for support. Just because Charlie was the first to offer his hand does not mean he was worthy of keeping hers.
11. Kelly Stables, aka Melissa
Look at that adorable face! Kelly Stables is so precious, she reminds us of a slightly younger and more sex’d-up version of Kristen Bell! Melissa is one of the kindest spirits to ever enter into the show: she’s forgiving, understanding, compassionate, kind, and nurturing. Perhaps those qualities are what drove both Charlie and Alan to engage in a romantic relationship with her in the first place. Though it didn’t work out well for either of them, both of them gave a good hearty chance with Melissa and she wasn’t able to make it work. Why? Because not only is she too good of a person for either of them, she’s way too hot for either of them! Even just watching her bounce around in her pajamas was enough to get us excited. It’s too bad that Alan couldn’t make things work with Melissa, because she had to be one of the hottest ladies that he ever landed.
10. Liz Vassey, aka Michelle
If Charlie had played his cards right, this gorgeous woman could have wound up being one of Charlie’s greatest loves. Michelle, played by the stunning actress Liz Vassey. However, her life was packed with simply too much hotness for Charlie to handle. Michelle was a dermatologist who met Charlie by having him as a patient, when she removed a mole from his buttocks. Even after that completely non-sexy meeting, the two managed to hit it off and date for a while. Charlie soonafter met Michelle’s daughter, an amateur p*rn star who Charlie was (obviously) immediately into. After the young lady said she didn’t date older men, he went back to Michelle (who actually TOOK HIM BACK!) and the two dated for a little while longer until Michelle left him after suspecting he was secretly in love with the crazy neighbor Rose. He can think Michelle is insane all he wants; we all know that truthfully, Charlie is a loon, so his opinion is moot.
9. Teri Hatcher, aka Liz
This is another relationship that clearly was doomed from the start, one that viewers could see from a mile away that was only going to be toxic and destructive and upsetting- though perhaps in the funniest of ways, so that we could laugh at their pain. Liz, played by Teri Hatcher (who is much better known for her incredibly sexy role in Desperate Housewives), was the sister of Alan’s ex-wife, Judith. It’s revealed early on in the episode that she’s in that Liz and Charlie hooked up in the coatroom while Alan and Judith were getting married; Charlie talks about the encounter like it was the best thing that ever happened to Liz and she probably would die for a reunion. But in reality? Liz couldn’t give two craps about Charlie and hardly remembers who he is at all. And why? Because Charlie is the kind of person women remember with regret and try to drink away the memories of, not the guy women reminisce fondly on.
8. Rachel Cannon, aka Chloe
Do we really need to even talk about this one? Come on, Rachel Cannon is a complete stunner! Though the actress hasn’t exactly hit it big yet, she’s been able to flaunt her good looks on plenty of shows, including Fresh off the Boat, Mad Men, and The Big Bang Theory. In Two and a Half Men, she played Chloe, a girlfriend that Charlie was more anxious to get rid of than get on top of. He changes his mind and tries to win her back, but only after she starts falling for the gorgeous and strapping handyman (played, of course, by Enrique Iglesias). Of course Charlie fails to win Chloe back after Fernando (the handyman) wooed her! Not only was Fernando more appreciative of her, respectful to her, sensual to her, and kind to her, he was simply a better man than Charlie was! When Charlie sets a woman’s bar so low, almost anyone can overcome it!
7. Heather Locklear, aka Laura Lang
Oof. Heather Locklear. Be still our beating hearts.
To be fair, we’ve been ragging on Charlie Sheen a LOT in this article. Sorry, Charlie; it’s not that we don’t like you! It’s just that… you’ve devolved into a human being that has less care for himself than humanity does for him, and that certainly doesn’t help your cause. But in this particular case, Charlie *Harper* was certainly a better man than Locklear’s character, Laura Lang. Laura slept with Charlie (creating a HUGE conflict of interest, since she was Alan’s divorce attorney) and made him promise to be available for sexual favors whenever she called upon him. When he backed out of the deal, Laura threw Alan under the bus in his divorce agreement as an act of revenge. Charlie can be a real dirt bag, but at least he wasn’t as vicious as this malevolent, stunning, manipulating, gorgeous, hypnotizing vixen.
6. Jeri Ryan, aka Sherri
Sherri was another one of Charlie’s girlfriends that liked things her way on her time and how she liked it, especially between the sheets. While Charlie struggled with his relationship with her due to power struggles, he admitted that Sherri was just a female version of himself: demanding, insatiable, hard to get, and ultimately impossible to stay with. The two broke up due to Charlie’s need to have the upper hand in the relationship, though it didn’t really work out well for him either. Sherri was played by Jeri Ryan, who is RIDICULOUSLY sexy. An all-natural woman, Jeri is much better known for her huge roles in Star Trek: Voyager, Body of Proof, and Boston Public- in all cases, she was stunning and an amazing actress and one of the best parts of her show. She’s probably a character you remember strikingly well from Two and a Half Men, too, as she’s always got a presence to remember.
5. Emmanuelle Vaugier, aka Mia
Mama mia. Goodness gracious.
We were going to give you a picture of Mia from the series, but we’re pretty sure you can all remember Mia. You do, right? She was the dance instructor that was teaching Jake ballet in order to allow Charlie more time to talk to her. Once Charlie and Mia did start dating, she held out on him and decided the relationship needed to grow before sex could happen. Charlie relented for a while- who wouldn’t try to take a shot at this beauty? Unfortunately, Mia is a good influence on Charlie as the two get engaged and it ruins the relationship: she tries to convince him to give up smoking and booze and unhealthy foods and it turns out to be too much for Charlie. In the end, they break off their engagement right before the big day because… well, because Mia is an amazing and sexy woman that tries to give him a better life. Shame on her…
4. Denise Richards, aka Lisa
Lisa was a really interesting character on a number of levels. First of all, the character is introduced as one of Charlie’s ex-girlfriends; someone he lived with but the two split up because Charlie was not willing to be in a committed relationship. Though the two try and try again in brief, hesitant stints, Charlie can never be the man that Lisa needs him to be. It’s a sad relationship in the show, mostly because… it’s real. Denise Richards (who played Lisa) is Charlie Sheen’s real life ex-wife, and their relationship ended because of his unhealthy habits and his propensity to stray from their relationship. Though she’s been a doll to support him since the divorce on numerous occasions in his career, it’s really sad to see that Charlie isn’t just some fictional character that’s screwed up his life- he’s horrifyingly real. Denise, however, is living it up these days with her three kids, savoring independence in her career and life.
3. Jud Tylor, aka Sissy “Didi”
Sissy, or “Didi” as Charlie called her, was one of the few characters in the series that we might have been moderately happy Charlie wanted to and managed to get away from. Sissy was downright dumb, even more so than Charlie usually likes. That means she was dumber than Kandi, dumber than Chelsea, dumber than Mia… She. Was. Dumb. That’s not really debatable. HOWEVER, she was still a catch in the world of Charlie Harper. Played by actress Jud Tylor, who has also starred in Charlie Wilson’s War, 42, and Home of Phobia, the character was downright stunning. Sure, maybe she couldn’t maintain a solid conversation, but what more does Charlie want? He’s really just looking for the perfect body to match his speed between the sheets, right? And that’s exactly what Sissy was, if he could have managed to stay with her! Who cares if she wasn’t the smartest character to enter the series; she was certainly one of the sexiest.
2. Jodi Lyn O’Keefe, aka Isabella
Again… do we need to say more? Jodi Lyn O’Keefe is a stunning actress that looks like she could devour you in every way possible. Her piercing eyes, he silky hair, her soft curves, and her plump cheeks are enough to make any man weak in the knees. You probably best know her for her time in the movie She’s All That as the main antagonist, but she’s also been on Nash Bridges and Halloween H20: 20 Years Later. No one can deny her beauty and sex appeal, not even Charlie Harper. She played Isabella in the series, a woman who only engaged in relations with him for the purposes of her satanic cult- sounds like a healthy relationship, right? Why in the world would Isabella be with Charlie? Because she wanted to convince him to give birth to a new satan that would bring terror into the world. Think that through: she dated him because she thought he would help her SPAWN SATAN.
1. Ming Na-Wen, aka Linda Harris
Ming Na-Wen is gorgeous. Though her character was short-lived in Two and a Half Men, the producers should have considered themselves lucky to have gotten even that time, and Charlie Sheen should be kissing her feet for lying near him naked. These days, the actress is best known for her roles in Agents of S.H.I.E.L.D., though she was also in E.R. and was the iconic lead in Disney’s Mulan. On Two and a Half Men, she played a character that suited her intellect and sex appeal. A judge that Alan introduces to Charlie who is disgusted by him, though Charlie is infatuated with her. Charlie ends up never being enough for Linda, usually due to alcohol and substance abuse- which just about makes sense. Linda was way too good for Charlie, even with the baggage of a young son and an ex-husband. This sexy woman tops our list of babes who were too hot for Charlie Sheen.
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