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Two And A Half Men: 10 Casting Decisions That Hurt The Show (And 10 That Saved It)

Say what you will about Two And A Half Men, and plenty of its critics, detractors, fans, and cast members have; but the show lasted for over a decade. 262 episodes that will live on forever in syndication and make money in perpetuity for everyone involved in the series. Like most traditional sitcoms, the premise is simple. A recently divorced, straight-laced sad sack and his young impressionable son moves in with his devil-may-care, hedonistic jingle-writing brother.

Thanks to the very much publicized backstage and off-screen shenanigans of the series’ original star, Charlie Sheen, the show has to pivot big time and become a slightly less debauchery-filled series. But the void left by Sheen’s departure was filled with a never-ending relentless series of storylines that basically kept Alan becoming more and more of s sniveling fool.

Meanwhile, Sheen’s replacement, Walden Schmidt at first seemed to have a heart and was just naive, but he too got corrupted by this motley crew of characters that he was surrounded by. Over the course of the show, there were all kinds of stunt casting and guest stars who rolled into Charlie Harper’s Malibu beach house. Back when the show started, networks still cared about sweeps week. Sometimes the casting choice was an inspired great addition that made for a few memorable episodes, and others were a bit of a head-scratcher.

For better or worse, whether it was for one show, or they were a reoccurring cast member, here are 10 Casting Decisions That Hurt Two And A Half Men (And 10 That Saved It).

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Amber Tamblyn in Two and a Half Men
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20 Hurt – Amber Tamblyn

Amber Tamblyn in Two and a Half Men

When the show’s eleventh season began, Amber Tamblyn was cast as Charlie’s long-lost illegitimate daughter, Jenny. While the young acclaimed actress did a serviceable job, it was clear that creator Chuck Lorre and the rest of the writers were struggling during the past few seasons of the show.

It was what plenty of sitcoms do when the lead leaves, try to plug the void any which way you can. Kutcher could only do so much as Walden without becoming a clone of Charlie Harper. Might as well create a long-lost family member to be that clone. The obvious ploy just meant the series was on its last legs.

19 Saved – Ashton Kutcher

Ashton Kutcher and Jon Cryer in Two and a Half Men

When the Martians came to claim their tiger blood-laden favorite son, Charlie Sheen; it was a meltdown of catastrophic, seldom seen before proportions. Sheen’s comments and behavior became the laughing stock of Hollywood and had plenty of his friends worried about him. But most importantly, it put the future of the series in doubt.

Then Chuck Lorre announced that the show will continue, speculations abound as to what the creative team would do – recast Charlie? Bring in another brother? Invent a whole new character? When Ashton Kutcher was announced to take over, we knew we’d have a much different show on our hands. Kutcher brought a different kind of sensibility to the show and the injection of new non-Martian blood helped it chug along for a few more seasons.

18 Hurt – Judy Greer

Judy Greer’s comedic sensibilities are fantastically twisted - just with her on Archer. But she was wasted on Men, not once but twice. Sitcoms often cast actors multiple times in multiple roles. But they’re usually acting in small roles. Greer was cast and recast in two different but fairly important supporting roles.

In both of them, she was intoxicated. First, she played Herb’s younger sister who had a thing for Charlie. Then, she played Walden’s ex-wife, Bridget. While Myra might have some longevity had she not been written off the series, Bridget would constantly act like Walden’s mother and zap humor out of any scene she was in.

17 Saved – Charlie Sheen

Sure, he was the first person cast on the show, but what an inspired choice! Remember the concept - he’s playing a carefree hedonistic jingle writer. While Sheen didn’t write jingles for a living, the bad boy actor was known for his party boy, wild child behavior.

The character was written with him in mind. Casting anyone else would have been a huge detriment to the show. It might not have lasted the eight seasons it did with someone else playing Charlie.

16 Hurt – Mimi Rogers

During the show’s final four years, a litany of new characters was introduced to switch up the format of the series. Mimi Rogers played Robin, Walden’s mother. Similar to Evelyn, she would do questionable things to and for her son. It was just another rehash of an old character’s traits.

Thankfully, we didn’t have to endure too many episodes with her. When you’re written to have raised your son alongside a monkey for science, it’s usually a clear indication that the writers aren’t trying very hard anymore.

15 Saved – Holland Taylor

As Evelyn Harper, the most conniving mother that ever lived, Holland Taylor was devilishly delightful to watch. Her banter with both Alan and Charlie we’re usually scene-stealing highlights. But she wasn’t always the perfect mother for the role. As the pilot was gearing up, another famous actress had been cast.

Blythe Danner was the original Evelyn. The actress certainly had the chops to play mamma Harper. But the actress also tried to take over the set, making “suggestions” wherever she could. The producers recast the part and Taylor would be an integral part of the show’s fabric.

14 Hurt – Brooke D’Orsay

Walden Schmidt was a wealthy man who got mountains of money and plenty of people who know who he is. So, when he meets Kate, an aspiring fashion designer and she actually doesn't know who he is, Walden’s instantly smitten. Instead of revealing himself, he acted like a poor man, Sam Wilson; before finally revealing himself.

Between the character and the actress, Brooke D’Orsay, the whole relationship didn’t feel genuine at all, and not because Walden wasn’t being honest. There was just no chemistry between the two characters.

13 Saved – Jane Lynch

A young child at the heart of a divorce might need someone to talk to besides their parents, or womanizing uncle. Jake started seeing Dr. Linda Freeman, a child psychologist. Later on, she would also start treating Charlie, Alan, and later, Walden.

She generally played the straight man to the main characters, when they needed a sounding board. Combined with her no-nonsense way of seeing right through all of them, Jane Lynch owned the part and like any great guest star made each appearance memorable.

12 Hurt – Ashton Kutcher

Yes, you’re reading that correctly. Ashton Kutcher was able to save the series by being cast as Walden Schmidt. But the entire series was not better off for it. Sitcoms, by their very definition, are virtually the same gags and yuks every week, just a different story. Kutcher being cast instantly changes the situation.

There wasn’t really any choice – either cast a new lead or end the show and put a lot of cast and crew out of work. Kutcher knew he’d be sending a lot of fans to their remotes to change the channel. By the nature of his casting, the show inevitably changed.

11 Saved – Graham Patrick Martin

The older Jake got, the dumber he got too. Perhaps if you cane from the same ridiculous situation he came from, you might be worse off for it too. The series kept playing him as your stereotypical stoner, slacker teenager. He would eventually need a friend to have shenanigans with.

Graham Patrick Martin played Lyndsay’s son Eldridge on the series last few seasons. He gave Jake someone his own age to relate to, and the pairing became the show’s own version of idiotic duos like Wayne and Garth, or Beavis and Butthead.

10 Hurt – Miley Cyrus

Since one of the show’s stars had done all he could to tank the thing, might as well cast an actress who had seemingly done all she could to tank her own career. The show has cast Miley Cyrus to play Missi - an eventual love interest for Jake. She came into the series as a family friend of Walden’s.

Big star castings on a series are not uncommon at all, and in some ways,  Cyrus seemed right up the show’s alley. But without enough prominent scenes or a story arc, it was stunt casting for the sake of it; which is never a good thing. Missi could have been played by anyone.

9 Saved – Kathy Bates

During the run of the show, Charlie always had delivered not-so-subtle hints that he wanted his brother to quit mooching off of him and move out. He finally got his wish, but only after he had passed away. Walden asks Alan to leave, who suffers a heart attack due to the stress. In his hospital bed, he meets Charlie’s ghost, played by Kathy Bates.

Bates has the time of her life channeling Charlie Sheen and messing with Alan. It’s one of her best performances, and one of the best episodes of the Ashton Kutcher run (“Why We Gave Up Women”). She would win an award for her performance.

8 Hurt – Michael Bolton

When a joke is so very tired, it’s time to pack up the show and leave. That’s why when Michael appeared on Two And Half Men, it was time for the series to Bolt(on). Walden was so rich that he was able to hire Michael Bolton, not once but twice to come to his aid.

Both the Walden character and the show had enough clout to hire any celebrity they wanted, and the writers thought that Michael Bolton turning up to sing his tired ballad, “When A Man Loves A Woman,” and bed both Alan and Walden’s mothers would be sitcom gold. It wasn’t at all. Just another death knell in the series’ coffin.

7 Saved – Jodi Lyn O'Keefe

Of course, Charlie wouldn’t care at all that he’s dating a wild demonic worshipping succubus who seeks to use Charlie as a human sacrifice for having a baby with him. That’s a Tuesday for the womanizing jingle writer. Alan and Jake were terrified, but Charlie didn’t seem to mind the boils and marks that kept appearing on his person. The only thing that stopped Isabella was her head witch - Evelyn.

Women constantly came in and out of the beach house. But Jodi Lyn O’Keefe playing Isabella was a stroke of casting genius - most men wouldn’t mind her condemning them to a life of servitude. The episode also had one of the show’s funniest bits - Evelyn as the Wicked Witch and the boys were the flying monkeys.

6 Hurt – Courtney Thorne-Smith

One would think that even Alan wouldn’t be so depressed and down on his luck that he would date a woman who berates and ridicules Alan as much as his own family does. Then again, most people tend to gravitate towards what they know.

Played by Courtney Thorne-Smith, not only was Lyndsay out of Alan’s league, she too was just as miserable dating Alan as he was being made to feel by her. Sometimes it’s just funny watching how much a person can be belittled. That’s not woke-speak; that’s just comedy 101.

5 Saved – Kelly Stables

When these characters are on our TVs weekly, and then daily thanks to syndication; we occasionally want to and enjoy seeing them happy. Before he turned into a full-on lecherous creep, Alan got to have a little bit of happiness with his secretary turned girlfriend Melissa.

Kelly Stables played Melissa with the right kind of bat crap zaniness that was needed for the show. Even during their nine million break-ups, she always seemed to know what would be best for Alan - which was usually for him to stop being Alan.

4 Hurt – Edan Alexander

In the manual entitled “How To Sink A Sitcom,” please turn your books to page 237, chapter 12 - Introducing A New Kid. Reference Oliver on The Brady Bunch or Seven on Married...With Children, a new kid is almost always bad for the show. In an almost act of defiance, Men did that very thing.

Louis didn’t add a single thing to the final season of the show. The actor, Edan Alexander didn’t bring anything to the role either, but perhaps he wasn’t supposed to. The entire final season was one long bad joke about Alan and Walden pretending to be lovers just to adopt the kid who doesn’t even show up in the finale, which is one long rag on Charlie Sheen.

3 Saved – Carl Reiner

Comedy pioneer Carl Reiner adds to just about anything he’s a part of. To this generation, he’s best known as Saul in the Ocean’s Eleven film series. But for a real education on how funny the guy is, go check he and Mel Brooks’ comedy album 2000-Year-Old Man.

Two And A Half Men would make use of Reiner from time to time by casting him as Marty Pepper, a retired TV producer, who is dating Evelyn and always tried to offer fatherly advice to Charlie and Alan, and later Alan and Walden; normally to awful results.

2 Hurt – Jennifer Bini Taylor

Jennifer Bini Taylor the actress is statuesque and beautiful. As Chelsea, physically, she had everything Charlie would want in a woman. Emotionally though, this is Charlie Harper, one of the most disconnected people in sitcom history. The only reason we knew he loved Chelsea, is because he told us.

But there was never any real chemistry between Taylor and Sheen. Part of the joke is that she got along better with Alan. Perhaps she should have dated Alan and the jokes should have been how Charlie was insanely jealous.

1 Saved – Ryan Stiles

If you ever want to torture someone by making them laugh themselves to death - you’d have good luck strapping them down and forcing them to listen to Ryan Stiles on episodes of Whose Line Is It Anyway? The guy is laugh-a-second hysterical on the show. On Men, he was just as good, playing Herb, Judith’s second husband.

His comedic styling fit the show nicely, not only because of how he played off of Charlie and Alan, but because of how well most of the audience knew his comedic timing.

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What do you think about these casting decisions on Two and a Half Men? Let us know in the comments!

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