Two And A Half Men: 10 Character Additions That Hurt The Show (And 10 That Saved It)

Angus T Jones Charlie Sheen Jon Cryer Two and a Half Men

Not many sitcoms last 10 seasons, let alone 12. Two and a Half Men broke all the rules of network TV as its raunchy approach captured the hearts of fans for years. The combination of Charlie Sheen, Jon Cryer, and Angus T. Jones was lightning in a bottle – and it made all the cast members and crew very rich in the process. After a detailed and well-publicized break-up with Sheen, the show added Ashton Kutcher to the ranks and carried on for a few more seasons. Undoubtedly, the unheralded star behind the scenes was creator Chuck Lorre, who managed to navigate the egos, drama, and everything in between as he produced this smash-hit sitcom for years.

However, Lorre credits his longtime team of writers as the real stars: “These are passionate, creative people; there are no pushovers,” he told TV Guide. “Out of the friction comes something better than what would happen if I had autonomy. Out of that cauldron of dissent comes a better show.” Across 12 seasons, these writers penned many characters that appeared and disappeared on Two and a Half Men. Some of them made an impact, while others just made up the numbers. So, let's take a deeper look at 10 Character Additions That Hurt The Show (And 10 That Saved It).

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Ashton Kutcher and Jon Cryer in Two and a Half Men
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20 Hurt: Walden

Ashton Kutcher and Jon Cryer in Two and a Half Men

To say that anyone looked forward to Walden Schmidt's introduction on Two and a Half Men would be the overstatement of the century. After Charlie Sheen's departure from the series, Ashton Kutcher was brought in to portray Walden, a handsome billionaire who was a lot nicer to Jon Cryer's Alan than Charlie was (both in real life and on screen).

Unfortunately, Walden wasn't ever popular with the fans; most people refuse to acknowledge that it's even the same show after Walden's introduction. In an interview with Howard Stern, Kutcher said he understood their disappointment: “There was a lot of people that were huge fans of the show that did not like me on the show. I get it, because it's not the same show.”

19 Saved: Kandi

April Bowlby and Jon Cryer in Two and a Half Men

While Charlie was always lucky in love (and lust), Alan found more success in mooching off his brother. Fortunately, there's a lid for every pot – even if it's only temporary. Kandi (April Bowlby) became Alan's love interest and second wife. She was portrayed as a dimwitted and innocent 22-year-old who was involved with both Harper brothers.

The storyline was terrific because Kandi was completely out of Alan's league. Eventually, his own insecurities and Kandi's realization that she could do better resulted in their marriage falling apart. As expected, Alan came back to Charlie's Malibu home with his tail between his legs.

18 Hurt: Chelsea

Jennifer Taylor and Charlie Sheen in Two and a Half Men

One of Charlie Sheen's last storylines on the show featured his character in a relationship with Chelsea (Jennifer Taylor). While the committed life was utilized as a way to stir up the hedonist lifestyle, there was never a genuine spark between Charlie and Chelsea.

Make no mistake, Charlie's faults were apparent for anyone to see, but he seemed to really care for her. The way that Chelsea spoke and treated him, however, bordered on the obscene. She wanted to mold him into something he wasn't, and the fans didn't like it. If he didn't bend to her whim, she threatened to end their relationship. So, who was the real troublesome one here?

17 Saved: Herb

Ryan Stiles and Jon Cryer in Two and a Half Men

The “ex-wife's new husband is bad and more successful” trope has been played up for years in film and television. This is why it was refreshing to see how Two and a Half Men handled Dr. Herb Melnick, played by Whose Line Is It Anyway? alumnus Ryan Stiles. Herb was introduced as Jake's pediatrician and Judith's second husband.

Eventually, Charlie and Alan struck up a friendship with the awkward, but hilarious, Herb. Watching as Herb craved the male bonding time with the Harper brothers was endearing and heartwarming, even if their bad ways inevitably rubbed off on him. Judith and Herb divorced after he got together with his receptionist, but they reconciled later.

16 Hurt: Lyndsey

Jon Cryer and Courtney Thorne-Smith in Two and a Half Men

Lyndsey McElroy (Courtney Thorne-Smith) served as Alan's on/off love interest from season seven until the end of the series. At one point, she was even engaged to him, and lest we forget, she also had a – ahem – moment with his ex-wife Kandi in season 10.

Unfortunately, Lyndsey was toxic for Alan and you never got the impression that she cared much for him from the get-go. In comparison to Charlie, Alan had fewer on-screen romances or potential suitors, so fans naturally cheered for him when he got his chance. However, his relationship with Lyndsey was never celebrated nor good for him. You could probably say she was the worst love interest Alan had on the show.

15 Saved: Jenny

Amber Tamblyn in Two and a Half Men

After the departure of Charlie Sheen from the show, there was a need for someone to pick up his wild and wacky mantle. It wasn't Ashton Kutcher's Walden who did so, but Amber Tamblyn's Jenny who was Charlie's long-lost illegitimate daughter. As expected, she shared most of her old man's vices and personality quirks.

Not only did Jenny provide some comic relief and head-shaking moments, but she also brought a fresh angle for the show. In some instances, she'd steal the women right out from under Walden's and Alan's noses. While she might not have received the character-defining arc that she deserved, she certainly added more color and fire to the lackluster final seasons of the series.

14 Hurt: Bridget

Judy Greer and Ashton Kutcher in Two and a Half Men

Well, this is awkward. Judy Greer originally appeared as Myra Melnick, Herb's younger sister, in season four of Two and a Half Men. While she didn't have a massive role, she appeared for two episodes and started a relationship with Charlie, even though she was engaged at the time. Then, in season nine, Greer returned, but this time, as Bridget Schmidt, Walden's ex-wife.

Die-hard fans immediately scratched their heads about this. It's the equivalent of Chris Evans appearing as Johnny Storm/Human Torch and Captain America in the MCU. It wasn't the first time that the series recycled actors for multiple parts, but considering Greer's earlier role as an important character's sister, this was a puzzling decision.

13 Saved: Courtney

Jenny McCarthy and Robert Wagner in Two and a Half Men

One of the best storylines from Two and a Half Men involved Teddy (Robert Wagner) and Courtney Leopold (Jenny McCarthy). Teddy was engaged to Evelyn and quickly won over Charlie and Alan with his flash and demeanor. Teddy's “daughter,” Courtney, stole Charlie's heart and he fell hard for her, even though others were against this relationship for obvious reasons.

The big twist arrived when it was revealed that Courtney was really Sylvia Fishman and Teddy was Nathan Krunk. They were lovers and scam artists who planned on cleaning out the Harpers. The truth is, Courtney was the first person on the show to receive Charlie's genuine affection – and he even forgave and dated her again when she was released from prison.

12 Hurt: Judge Harris

Ming-Na Wen in Two and a Half Men

When Judge Linda Harris (Ming-Na Wen) was introduced in season five, she seemed like the perfect foil for Charlie. After all, she was a law enforcer and Charlie was the rule breaker. It had all the makings of a catastrophe waiting to happen – and isn't that what we love about sitcoms?

Unfortunately, Judge Harris only stuck around for a little while and the fun hadn't even started yet. The character felt like a real lost opportunity and the writers could've done so much more with her. Sadly, she'll go down in the history books as just another of Charlie's exes instead of having served a purpose on the show. It was also a waste of Wen's acting ability.

11 Saved: Eldridge

Jake and Eldridge in Two and a Half Men

The early seasons of Two and a Half Men looked a little lonely for Jake. While his father and uncle had each other to relate to, he hardly had anyone his age around him. Yes, there was the odd storyline or two where Jake visited or had a friend over at the Malibu house, but he seemed alone most of the time.

This changed when Alan dated Lyndsey and Jake befriended her son, Eldridge (Graham Patrick Martin). They were two peas in a pod, allowing their dimwitted nature and attraction to trouble bring them together. Finally, Jake had a friend, who was just as much of a doofus as he was, and everyone deserves that.

10 Hurt: Robin

Ashton Kutcher and Mimi Rogers in Two and a Half Men

There was a tendency to enhance the parent-child conflicts in Two and a Half Men. In the latter seasons, we saw the struggle between Walden and his mother, Robin (Mimi Rogers). Robin did more than a few despicable things to ensure that she'd be at the bottom of his Christmas card list, but Walden continued to love her anyway.

Unfortunately, this character was far too predictable for our liking. You could call her character arc a mile away and Robin only served to annoy the viewers at home more than the ones on screen. Fortunately, she only appeared in a handful of episodes across the final seasons, so we were spared from her insipid ways.

9 Saved: Isabella

Jodi Lyn O'Keefe and Jon Cryer in Two and a Half Men

As expected, Charlie racked up more than a few girlfriends on the show. We'd see them come and go; sometimes only appearing for a split second on the screen. While most of his conquests didn't last more than an episode, there were several who left their mark in a big way.

Isabella (Jodi Lyn O'Keefe) appeared in less than a handful of episodes, but she certainly made her presence felt. For one, she was part of the occult and decided to curse him. She also freaked out Jake and Alan as she planned on having a child with Charlie who would've been the antichrist. The only thing that drove her away was Evelyn.

8 Hurt: Missi

Miley Cyrus and Angus T Jones in Two and a Half Men

Ah, the celebrity appearances on Two and a Half Men. There were more than a few familiar faces across the 12 seasons, with some more deserving of their spots than others. One who didn't was Miley Cyrus, as she went through her edgelord phase and appeared as Missi in season 10. Of course, Missi was introduced as Jake's love interest and ended up breaking the poor boy's heart.

Even though her castmates praised her for showing up and being a pro, the people at home – bar her fanbase – weren't left too impressed. Maybe if she had a longer arc, Missi might've gone down well. Alas, it just felt like Miley playing Miley on the series.

7 Saved: Melissa

Melissa (Kelly Stables) brought the laughs during her tenure on the show. At first, she had a relationship with Charlie that went south, then, she dated Alan. In all honesty, she fit Alan like a glove and there was an entertaining and combustive dynamic between them. You could see it was going to end badly, but oh boy, did you want to watch it play out.

Eventually, their relationship ended after Alan... Well, after Alan was himself way too many times. Not only did he lose her as a girlfriend, but she also left her job as his receptionist. In fact, you could say that Alan's love life lost a bit of a spark after Melissa departed the series.

6 Hurt: Michael Bolton

Jon Cryer, Ashton Kutcher and Michael Bolton in Two and a Half Men

Look, we get it. Celebrity appearances make shows that little bit more special, and if you can secure a famous name, chances are, the average viewer might tune in to catch an episode featuring the star. But, this whole fascination with Michael Bolton isn't funny or appealing – and it never has been. This guy isn't Chuck Norris, so why are we still going nuts over him?

As the show lost all its hilarity, it decided to throw in Bolton for an extra measure. He was introduced as a friend of Walden's and popped up in a couple of episodes. Of course, he ended up getting together with Walden's and Alan's mothers, but seriously, who cares?

5 Saved: Mia

Charlie Sheen and Emmanuelle Vaugier in Two and a Half Men

If you think about it, it's understandable why the relationship between Charlie and Mia (Emmanuelle Vaugier) never worked out. It would've signaled the end of the show had the two married; they would've lived happily ever after and Alan would've needed to get his life together. Truth be told, it would've been the perfect way to cap off the series had the two gotten together for good.

Every relationship after Mia didn't work as she was the one who truly captured Charlie's heart. In fact, you could argue that Charlie's arc became stale after their romance ended. She might've only had a recurring role on the series, but Mia ended up becoming the perfect partner for Charlie.

4 Hurt: Marty

Carl Reiner, Amber Tamblyn and Holland Taylor in Two and a Half Men

Much like her eldest son, Evelyn had numerous suitors throughout the series. In most instances, they didn't last too long and departed before the relationship gained some steam. The one who lasted quite some time (at least on screen) was Marty Pepper (Carl Reiner), who eventually became Evelyn's sixth husband.

The thing is, Marty's shtick has been seen many times before in other shows. He's the much older man, who makes mistakes and allows things to happen because he's too grumpy to care. Sure, he had a few endearing moments, especially when Walden and Alan were his best men at the wedding, but Marty proved to be a stick in the mud for most of his appearances.

3 Saved: Tammy

Jaime Pressly and Emily Osment in Two and a Half Men

Watching Jake grow up, it was evident that he wouldn't have a normal life. After all, the influence of his father and uncle were too strong. Jake was destined to have an “exciting” life filled with numerous and wacky twists and turns. One of his more interesting angles was getting involved with Tammy (Jaime Pressly), who was much older than him and had three kids.

While Tammy wasn't seen as a catch in the beginning, she seemed to show genuine feelings for Jake. In fact, she wouldn't allow them to marry unless they brought their families together. As it turns out, Jake had the same idea, as he got together with her eldest daughter, Ashley.

2 Hurt: Kate

Brooke D'Orsay and Ashton Kutcher in Two and a Half Men

By the time Walden entered the series, everything he touched turned to rubbish – including his relationships. Oddly, Walden decided to create a new persona, Sam Wilson, and meet someone who wasn't after his money. He fell for Kate (Brooke D'Orsay), and after finally admitting who he really was, he brought her into his life and invested in her fashion line via Alan.

The two broke up and got back together again, before Walden called it quits because of his feelings for Vivian. While Kate looked like she might be the one, it was evident after the first few episodes that she wasn't. This was a relationship that went nowhere and had no payoff, which was a complete waste of time.

1 Saved: Charlie's Ghost

After Charlie Sheen's departure from the series, it was clear that there was no love lost between him and showrunner Chuck Lorre. Lorre and the writers used every opportunity to stick it the series' original lead star, and some of the quips and angles even bordered on the petty side, if you ask us.

The best thing they did, though, was introduce Kathy Bates as Charlie's ghost. The explanation given was that his spirit lives in the underworld and he's forced to eternally live in a woman's body due to his womanizing ways. Bates, as expected, was fantastic and played the part with humor and pizzazz. In every scene she was in, she stole the show – and even won an Emmy for it.


Tell us, which other character additions hurt or saved Two and a Half Men? Sound off in the comments!

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