Two and a Half Men: 5 Times We Felt Bad For Charlie (& 5 Times We Hated Him)

Charlie Harper was one of the most exciting characters on primetime sitcom television, and Charlie Sheen was the highest paid TV actor thanks to the long-running role on Two and a Half Men.

As a playboy jingle writer, he lived a lavish life as a bachelor until his younger brother Alan and his 10-year-old son showed up at his door looking for a place to stay after Alan’s wife threw him out.

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There were many times throughout the series that viewers felt bad for Charlie, but plenty of others when they hated him, too.

10 Felt Bad: He Had Financial Troubles

Remember that time when Charlie’s credit card was declined and he was left to feel embarrassed and confused? Turns out he was simply spending the money quicker than it was coming in.

As a successful jingle writer, he made pretty good money. But when he had to take financial advice from Alan and then borrow money from Rose, it was difficult not to feel bad for him when reality set in that he wasn’t actually invincible with a bottomless bank account.

9 Hated Him: He Cheated On Women

Over and over again throughout the series, Charlie cheated on woman after woman. It wasn’t necessarily cheating as it was that he simply used women to fulfill his desires, but he had no intention of pursuing anything real with any of them.

Sure, he did settle down from time to time, but his treatment of women overall made viewers despise him.

8 Felt Bad: Rose Kept Stalking Him

Charlie was in the wrong by having a meaningless one-night stand with Rose and treating her the way he did. However, she took it to another level when she proceeded to stalk him for years because of it.

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They sort of became friends and eventually even got married! But it’s tough not to feel bad for Charlie when you remember her doing things like gluing his cabinets shut or scaring off girlfriends with lies.

7 Hated Him: He Treated Women As Objects

Further to the previous point, Charlie didn’t just cheat on women but he treated them as objects. He’d often seek out women who fit the Barbie Doll look, who were thin, dressed provocatively, and weren’t exactly smart.

He’d sometimes go the other way and seek out women who were better suited to him but inappropriate in other ways, like Jake’s teacher.

6 Felt Bad: Alan Showed Up

When Alan showed up in the pilot episode looking for a place to crash with his 10-year-old son, viewers felt bad for Charlie. He was living the perfect playboy life with a different woman every night and here came his dorky brother to ruin it all.

Not only did Alan presumably want to stay for a bit until he got back on his feet, but he wanted to bring his child and upend Charlie’s life. And then he ended up staying permanently.

5 Hated Him: Slept With Judith’s Sister

When Alan and Judith started dating, Charlie didn’t like her and didn’t try to hide it. He didn’t want Alan to be with her so badly, in fact, that he even bribed his brother to leave her.

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He still attended the wedding but made sure to cause trouble while there and leave his mark. How? He slept with Judith’s sister in the coat closet!

4 Felt Bad: He Took Jake To The Hospital

In a season one episode, Charlie got offended when he found out that Alan had asked their cousins from Rhode Island to be Jake’s guardians if both he and his ex-wife and Jake’s mother Judith passed away.

Later on, Jake is left with Charlie who proves an irresponsible caregiver when he accidentally injures him. However, he shows his parental instinct by taking Jake to the hospital and caring for him like an uncle should, convincing Alan that Jake would be in good hands with Charlie after all.

3 Hated Him: Crashed Mia’s Wedding

While Charlie was a womanizer who could seemingly never be pinned down, he did, on a few occasions, find a woman he was ready to settle down with. But it never worked out in the end. One such woman was Mia, a ballet teacher with whom he broke up because she kept trying to change him.

They get back together, he proposes, but before getting married in Vegas, they break up because Charlie discovers Mia wants Alan to move out. Later in the series, Charlie finds out Mia is getting married and crashes her wedding. Not only does she turn him down, but his father also punches Charlie!

2 Felt Bad: Was Held Captive

As bad as Charlie was, no one deserved what Rose put him through. After finding him in bed with others, she kept him in a bunker for four years, pretending he was dead and even delivering a eulogy at his funeral.

Meanwhile, he was alive the whole time, suffering in solitary and brainwashed to think Alan and Walden were evil. Eventually after escaping and returning to get revenge, a grand piano fell on his head and really killed him. Ouch.

1 Hated Him: Ignored His Daughter

Yes, Charlie had a daughter. He got a random woman pregnant sometime in the late ’80s or early ’90s and while he knew of the child, a daughter named Jenny, he didn’t have any interest in being in her life. He did help the mother financially by sending checks monthly, and Jenny noted that the only time he wrote to her was to ask her if her friends were 18 yet.

This story only came to fruition in the 11th season, after the character of Charlie was long written off the show. Jenny appeared in several episodes throughout the series, played by Amber Tamblyn.

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