Let’s start this article off with a bit of honesty. There were two main reasons for why people loved Two and a Half Men so much. Whether you hated Charlie Sheen or not, you watched the TV show and never felt any guilt about it because it was hilarious. But more than the comedy, the two things that attracted most viewers to the old-school seasons of Two and a Half Men, which we will call the “real” seasons of the show, were the ridiculously beautiful women who appeared on screen, and the little fact that deep down each and every single one of us wished we could lead the life Charlie Harper led.
The show creators tried to maintain the pace and give the fans something similar when they hired Ashton Kutcher to replace Charlie. But let’s be real, nerdy-billionaire does not even come close to Playboy-deadbeat-drunk-jingle writer in terms of hilariousness in the way of life. And don’t even get started on Alan as a lead character. It doesn’t matter how much you love character development or how good the actor was, that character was terrible. Either way, today we will have a little blast from the past as we go through 15 juicy pics of ladies Charlie Harper dated during his glorious life in the TV show. We could also include a couple of ladies with whom Alan had the luck of going out with, and maybe even the occasional gal with whom either Charlie or Alan could’ve hooked up but didn’t for any kind of reason (this includes the Megan Fox episode where she was literally the finest piece of jailbait ever seen on television). But we will try to stay focused on Charlie’s conquests.
15 Lisa – Denise Richards
We are starting this list off strong and with good reason. There is no better way of talking about the girls with whom Charlie Harper had relationships than by starting with the one who was played by an actress who was actually married to Charlie Sheen. Yes, unless you have done a run through the show over these past couple years, you might not remember that back in season two, Denise Richards made an appearance in the series as one of Charlie’s exes, who had just gotten divorced.
Easy pickings for Charlie, right? Guess again, because our favourite jingle writer did not get to spend another night with this ex without paying a somewhat hefty fee, which this time had nothing to do with actual money but with helping her take care of the baby Lisa had during her marriage. But let’s just say that Denise Richards made taking care of the baby worth it for everyone.
14 Olivia – Krista Allen
Charlie and Olivia did not exactly get together during episode six of season one, but a previous hookup between the character played by Krista Allen and our protagonist resulted in quite the headache for Charlie’s mom, Evelyn, and her new boyfriend. Of course, as soon as Evelyn started dating a new guy and decided to introduce him to her boys, there was something Charlie did in the past that ended up compromising the whole ordeal.
When Alan and Charlie appear at their mother’s place to meet the new boyfriend, everyone quickly finds out that Charlie dated the guy’s daughter and left her in shambles as he did to most of the women who ever got to see the beach house in Malibu. There were no love scenes, nor did Krista Allen appear for another episode, but we will be damned if we did not hope to see Olivia back for a second appearance.
13 Michelle – Liz Vassey
We can count on our fingers how many older women our guy Charlie has even considered dating during his time in Two and a Half Men. This dude was all about the young, busty blondes who just happened to find their way to his Malibu beach house. But in season eight, one older woman managed to pick Charlie’s interest for a few episodes. Her name was Michelle, and she was four years older than Charlie, something that obviously surprised everyone.
There was just one issue with their two-episode relationship, and it was the fact that Michelle’s daughter was actually more of Charlie’s type than her mom. Seriously, this girl was a 20-year-old, bisexual, amateur porn star. You cannot make that stuff up. Somehow, Charlie managed to resist the temptation and go on having a relationship with Michelle until his longtime love interest, Rose, became the pivot in ending the short but sweet relationship.
12 Laura – Heather Locklear
It is no secret to anyone that Charlie Harper was a master in thinking with his downstairs head. And by a master, we mean that he usually let that head do most of the thinking, and that was how Charlie liked to live his life. And honestly, who can blame the guy? When you have that kind of money and that “knack” for getting with beautiful women, who wouldn’t do the same? Nevertheless, his tendency to use the downstairs head usually affected those close to him, and most often what happened was that Charlie sleeping with somebody would usually cause trouble for his brother Alan.
That was actually a cornerstone of the show. But Charlie never screwed over Alan as bad as the time when he slept with his brother’s attorney, Laura, played by Heather Locklear. That was the beginning of the end for Alan Harper, who never really had much to begin with, but after his brother dumped his attorney, had to give everything away to Judith in the divorce.
11 Sheri – Jeri Ryan
Have you ever heard about poetic justice?
Well, in the case of Two and a Half Men, we finally got poetic justice for the character of Charlie Harper when he met his match during season two, in a woman named Sherri. Charlie had always been notorious for playing around with the ladies and then discarding them as if they were yesterday’s garbage, which was clearly not cool on his part, but still added to the comedic appeal of the show. So perhaps in an attempt to make the character realize how bad it feels to be treated like he used to treat women, they created a character who literally just used Charlie for s*x.
There is no other way of saying it because that was all there was to it. This woman would literally call him over and then tell him to leave as soon as they were done. Still, not many single guys would be against having a deal like that with Jeri Ryan.
10 Isabella – Jodi Lyn O’Keefe
Boy, did Charlie know how to pick them or not? We had seen all kinds of women roam through the halls of the jingle writer’s Malibu beach house. But no gal was as creepy and terrifying as the dark figure of Isabella, whom he met in season three of the show. In perhaps one of the funniest episodes in the history of Two and a Half Men, Charlie somehow found this Satanist witch of a woman who decided that they would serve the dark Lord “horned one” together and bring a baby to the world that would cause destruction and mayhem. The bottom line is that this woman wanted Charlie to be the father of the antichrist.
And as creepy as it all was, we cannot blame Mr. Harper for going out with this gal in the first place. Even with all the quirks and creepiness, she was arguably one of the hottest women in the show.
9 Mia – Emmanuelle Vaugier
Here is one character that divided audiences all throughout her lengthy appearances in the series. No woman had ever gotten as close to marrying Charlie Harper as his favourite dancer, Mia. We had never seen that guy work so hard to get a woman than he did when he was after Mia. For God's sake, he convinced Jake to learn ballet for this woman.
Either way, when the prospect of Charlie getting married to Mia started looking dangerous to everyone who loved the show, it seemed like there was a lot on the line for Two and a Half Men. Not only Charlie’s status as a bachelor was at stake, but an entire way of life. Don’t get us wrong, Mia was as pretty as they came, but this woman tried to make Charlie quit smoking cigars, drinking, and eating meat. She literally wanted the complete opposite of Charlie Harper, and for that, we are glad things didn’t work out between them.
8 Lydia – Katherine LaNasa
They say some guys have a mother complex. We are most familiar with the “daddy issues” complex some women have. After all, taking advantage of that particular issue is something that the main character of Two and a Half Men was quite the master at. But the opposite worked for Charlie as well. Everyone knew that his terrible relationship with his mother undoubtedly influenced the jingle writer’s love life, but no one knew how bad it was until we were introduced to Lydia in season four.
Personality wise, this woman was the spitting image of Charlie’s mother, Evelyn. They acted the same, they were terrible people just like the other, and both of them treated Charlie like crap. Still, when Alan and the gang tried to warn him about what was really going on in that relationship, this guy denied it until it was impossible for him not to see the truth. Still, that was as entertaining an arc as we ever had on the show.
7 Chloe – Rachel Cannon
One thing that happened a lot in Two and a Half Men was the directors having the same women playing different characters. For example, the actress who played Chelsea actually played four different roles spread through five different seasons of Two and a Half Men. And there were others who also played more than one character. One particular case we would like to point out happened when Rachel Cannon managed to play two different characters during season four of the show.
First, she played Nina, a minor character who barely had any lines and was mostly there to help advance the plot of Alan being a stingy guy. However, in her second appearance, she was Chloe, Charlie’s girlfriend whom Enrique Iglesias’s character, Fernando, stole from Mr. Harper. And we all loved Charlie’s attitude and bravado for when he fought tooth and nail to get Chloe back, even though he eventually had to use his money to get the job done.
6 Wanda – Diora Baird
Sometimes the one-hit wonders are the best. Two and a Half Men had a lot of one-hit wonders, which, in this case, are women who appeared in only one episode of the show but looked so good that we wanted them to come back badly enough we almost wrote letters to the show creators. That was the case of Wanda, who, for lack of a better word, was one of Charlie’s “bimbos.” And even if you have a problem with that term, you might find it hard to dispute once you remember how this woman showed up blasted in front of Charlie’s door, saying that she wanted to do the business.
Of course, it had perfect timing since it happened while Charlie thought Chelsea was cheating on him with her ex-husband while at his own mother’s funeral, so it is only fair that Charlie wanted to get back on the same coin and Wanda was the perfect woman to help him with that.
5 Melissa – Kelly Stables
They say the best gifts come in small packages. In Two and a Half Men we had an excellent example of how that could very well be true. No one who was a fan of the show can deny remembering Melissa and how ridiculously hot she was despite the fact that she was only 5 feet tall. One of the recurring characters of the show for quite a long time, this little gal managed to conquer hearts not only of the other stars of the show but also of the audience. It was entertaining to see how she switched from a weekend of debauchery with Charlie to trying to maintain a stable relationship with her boss and soon-to-be boyfriend, Alan.
More than that, she was a hilarious character who also gave us the opportunity to meet her mother, a woman who never really seemed to have come back from Woodstock given how she was always so unbelievably high.
4 Kandi – April Bowlby
Kandi was arguably the hottest woman on the show. One of the few who had relationships with both Charlie and Alan, this airhead bombshell was literally eye candy for the viewers of the show. Sorry for the pun, we just couldn’t help ourselves. Nevertheless, Kandi was the kind of character these shows live for. Her lack of intelligence is nothing short of hilarious and her comedic relief aided the show so much that became was almost as important as the fact that she was drop-dead beautiful.
So yeah, we’re saying that Kandi was as entertaining as she was hot, which means a lot. We cannot even begin to fathom the amount of guys who only started to watch this series and kept going seriously after this beautiful redhead was introduced into the fold. It first seemed like she would be yet another of Charlie’s one night stands, but aren’t we all glad that she took a shining to Alan?
3 Mandi - Gail O'Grady
So we mentioned Kandi and how she might’ve just been the most beautiful woman ever to appear on Two and a Half Men, but here is someone who could give her a run for her money. The difference in age between the two is quite significant, but that is what made it all that more impressive for some fans when we found out just how hot Kandi’s mother was when she was introduced into the show.
It was one of the most pleasant surprises in the history of television when Mandi showed up at Charlie’s doorstep looking for her lost daughter. We all knew what was going to happen as soon as he locked his eyes on her, which made it all more entertaining when Alan found out that his brother slept with his future mother-in-law. Either way, Mandi won the award of Two and a Half Men’s top cougar by a long shot.
2 Liz – Teri Hatcher
Early in the show, we got to find out how Charlie’s primary goal in life is not just to write jingles, make a ton of money for not doing a lot of work, or having relationships with some of the most beautiful women we have ever seen. Something that is a very part of the character’s being is the fact that he has an urge to make his little brother’s life a living hell. All throughout the series we get to see how Charlie was cruel to Alan while they were young, growing up, and even during the show. We previously mentioned how sleeping with Alan’s attorney might’ve been the worst Charlie ever screwed up his brother, but then we remembered something that happened before the show.
During his brother’s wedding, Charlie actually had s*x with Judith’s sister in the coat room; a messed-up event that would have been forgotten if not for the fact that when Judith sister showed up during season one, she was played by none other than Teri Hatcher.
1 Courtney - Jenny McCarthy
Yeah, when push comes to shove, there is no other gal from the Two and a Half Men universe who could compete with good old Courtney Leopold. Sure, we said Kandi could’ve been the hottest woman ever to appear on the show, but once we got to take another look at Jenny McCarthy’s character, there was not much to discuss.
Jenny McCarty is already one of the most beautiful actresses of her generation. Put that together with the hilarious and mischievous character that is Courtney, and we have the perfect recipe for the woman who could take down Charlie Harper and get payback for all the other gals he has ever wronged. There is not a single honest bone in this woman’s body, but at the same time, there is not a single ugly bone either. Courtney was drop-dead beautiful, and she was undoubtedly the hottest woman ever to show up at that Malibu beach house.