Summary

• The best Two and a Half Men episodes hilariously showcase the dynamics of the titular Harper men, and later Walden Schmidt, blending acerbic wit with hilarious sitcom humor
• Two and a Half Men is at its best with episodes like "Salmon Under My Sweater" and "Squab, Squab, Squab, Squab, Squab" when Jake is bonding and clashing with his family.
• Womanizer Charlie Harper rarely faces consequences for his questionable actions, but he certainly does in "Bazinga! That's From a TV Show".

While the Chuck Lorre sitcom was never a critical darling, the best Two and a Half Men episodes showcase the hilarity of the titular Harper men, and later Walden Schmidt (Ashton Kutcher). As controversial a figure as Charlie Sheen is, there's no denying the chemistry he had with co-stars Jon Cryer, Angus T. Jones, and Holland Taylor. Always ready with a perfectly timed insult, the characters put the "diss" in dysfunctional family, and their radically different outlooks on life led to hysterical sitcom foibles that made the show such a hit.

However, the sitcom wasn't all funny hijinks, as the worst episodes of Two and a Half Men are prime examples of the sexist and homophobic humor that made many cringe at the series. But when Two and a Half Men was firing on all cylinders, the characters were relatable and the jokes were sharp. The show was such a hit that it survived two major cast shakeups with the departures of Schmidt and Jones, but the best Two and a Half Men episodes prove why the comedy lasted a whopping 12 seasons.

25 "Walnuts And Demerol"

Season 4, Episode 11

In the season 4 episode, "Walnuts and Demerol," Charlie is expecting to have a wonderful Christmas with only him and his date. However, as with the best Two and a Half Men episodes, things do not go as planned and everything seems ruined for the bachelor. This all comes to a head when Charlie's friends and family all show up at his home and refuse to leave, creating a giant holiday celebration that is Charlie's worst nightmare.

Two and a Half Men has some great holiday episodes, but this one really shook things up because, as is best on the show, Charlie wants nothing to do with his family or friends, or any holiday festivity that doesn't involve him getting some alone time with his date. The chaos that occurs delivers some big laughs, and with everyone there, it gives plenty of characters a chance to shine, especially Rose (who discovers the one boundary that Charlie has in his life concerning sex).

24 "An Old Flame With A New Wick"

Season 1, Episode 18

The first season of Two and a Half Men has some good episodes, and one of the best is "An Old Flame with a New Wick." This episode sees Chris O'Donnell (NCIS: Los Angeles) guest star on the show as Bill, a trans man who dated Charlie before he transitioned. This really shakes Charlie up when Bill starts to date his mom, Evelyn, which really throws the bachelor into an existential crisis as his parent is now dating his ex.

O'Donnell works hard to make the portrayal of a trans man respectful.

This episode really hasn't aged as well as others, but Charlie's discomfort when Bill starts dating his mom remains great, and at least O'Donnell works hard to make the portrayal of a trans man respectful in his own performance. It also works well when Evelyn never once overreacts to or judges Bill for his identity and has no problem at all dating him — until she learns that he had slept with Charlie, which is a dealbreaker. The jokes are also never at Bill's expense, which is a huge positive.

23 "Gorp. Fnark. Schmegle."

Season 7, Episode 8

This episode occurs during Charlie's relationship with Chelsea, easily one of the most stable and solid in his time on the show. However, things are never easy because Charlie has a lot of vices, and when Gail (Tricia Helfer), one of Chelsea's attractive friends shows up, it threatens to disrupt his entire relationship with Chelsea. With this friend staying at Charlie's home, invited by Chelsea, it makes it hard for Charlie to keep his thoughts and hands to himself throughout the episode.

However, what makes this episode so noteworthy is that Charlie works hard to remain a good boyfriend, and does his best to remain faithful to Chelsea and help her friend as much as he can without stepping over the line. He might not be perfect in this episode, but he tries his best, which is almost all anyone can expect from Charlie by this point.

22 "The Salmon Under My Sweater"

Season 2, Episode 10

Two and a Half Men is mainly about the romantic and familial relationships of the Harper men, and spends a limited time on Charlie's actual job as a jingle writer. In the season 2 episode, "The Salmon Under My Sweater," Charlie is writing a new theme song for a television show, and he wants to win over Jake with the new track. However, when the boy doesn't like the actual song, Jake and Charlie start working on it together. It's a rare heartwarming storyline on the cynical sitcom.

However, the show also has a fun moment for fans who want to see Alan's awkwardness up close, as this includes Rose as her most manipulative. In "The Salmon Under My Sweater", Alan wants to get to know Rose better. The two even go on a date, which leads to a kiss, but things don't work out for them, and it is all just an experiment Rose is conducting. This is probably for the best, as Rose turns out to be bad news for Charlie, who she stalked and almost killed in the end after their engagement.

21 "The Two Finger Rule"

Season 6, Episode 19

"The Two Finger Rule" is a season 6 episode where Charlie and Alan get into a lot of trouble thanks to a day of hanging with their friends. It all starts when the brothers get drunk with Herb (Ryan Stiles) because they are all having problems with their romantic partners. They seem to be ready to just drown all their sorrows with alcohol, but it is shockingly Charlie who sees the light of the day at the end and realizes how pathetic they really are in these moments.

It includes some of the best ing actors on the show, including Stiles, Michael Clarke Duncan, and J.D. Walsh.

The episode works perfectly because it includes some of the best ing actors on the show, including Stiles, Michael Clarke Duncan, and J.D. Walsh. Together, they riff and deliver some great comic lines throughout. The chemistry is evident in this Two and a Half Men episode, and Herb steals every scene he's in, so it was great to see him front and center here. This is also a big episode because this specific group of characters never all get together again on the show after this.

20 "Merry Thanksgiving"

Season 1, Episode 10

"Merry Thanksgiving" sees Charlie trying to win back an ex-girlfriend after he finds out she's engaged. The episode stands out because it captures the essence of classic Two and a Half Men humor — unexpected twists, uncomfortable situations, and Charlie's complicated love life. It emphasizes the show's ability to take seemingly simple setups and turn them into hilariously intricate plots. Additionally, "Merry Thanksgiving" showcases the sitcom's ability to intertwine emotions and humor, as it includes one of the few instances of Charlie showing a more vulnerable side.

The episode's holiday setting amplifies the themes of family and connection, making the characters' interactions even more poignant.

The episode's holiday setting amplifies the themes of family and connection, making the characters' interactions even more poignant. The humor derived from the Harper family's unconventional Thanksgiving celebration not only provides laughs but subtly reflects on the nature of modern family gatherings. Through its adept mix of comedy, slight drama, and character development, "Merry Thanksgiving" is a memorable episode that resonates with viewers for its ability to blend the ridiculous with the relatable, making it a standout moment in the series.

19 "Fish In A Drawer"

Season 5, Episode 17

"Fish in a Drawer" is unique as it's a CSI crossover event. When a dead body is found at Charlie's house during Evelyn and Teddy's wedding preparations, a group of crime scene investigators steps in to solve the mystery. Bringing in the CSI team was an unusual but brilliant twist for the sitcom, straying outside the regular series formula. The mesh of dramatic crime-solving with the show's trademark humor, especially in scenes where the CSI team questions the eccentric habits of the Harper household, adds layers to the season 5 episode.

CSI writers Evan Dunsky, Sarah Goldfinger, Carol Mendelsohn, and Naren Shanker wrote "Fish in a Drawer" while Two and a Half Men writers and co-creators Chuck Lorre and Lee Aronsohn penned "Two and a Half Deaths", the CSI episode that aired that same week.

"Fish in a Drawer" brilliantly showcases the show's ability to integrate external elements while maintaining its comedic core. The interaction between the Harper family and the CSI team provides a refreshing contrast, highlighting the absurdity of the Harpers' lives through the eyes of the serious, methodical crime scene investigators. The clash of two very different television worlds serves as a clever device to explore character dynamics in a new light, with each member of the Harper household reacting in their own distinctive way to the investigation.

18 "That Special Tug"

Season 4, Episode 4

In "That Special Tug," Alan feels overshadowed by Charlie's accomplishments and struggles with his self-worth. It ends on a heartwarming note as the brothers come together, highlighting the underlying bond they share despite their differences. The episode shines a light on the emotional depth of the characters, especially Alan. Scenes where Alan expresses his feelings of inadequacy are both touching and relatable. The episode, with its emotional core, reinforces the fact that beneath the humor and antics, there's genuine affection between the characters.

"That Special Tug" does an exceptional job of weaving significant themes of sibling rivalry and self-acceptance through its humor and wit. It provides a deeper understanding of Alan's character, making his struggles and victories feel personal to the audience. The resolution, where Charlie and Alan find common ground, serves as a powerful reminder of the importance of family and acceptance.

17 "I Can't Afford Hyenas"

Season 1, Episode 14

In "I Can't Afford Hyenas," Charlie faces a conundrum when he doesn't realize how much money he has been spending and actually finds himself in a ton of debt. This problem forces him to reconsider his usual cavalier approach to overspending, even if he is a successful jingle artist. The episode is remarkable for showcasing that it isn't just Alan but Charlie who has problems too. Watching him grapple with unexpected hardships and navigate the unfamiliarity of being on a budget adds depth to the often shallow character.

"I Can't Afford Hyenas" also humanizes Charlie, a character often seen as the carefree, irresponsible playboy. By presenting him with financial challenges, the episode reveals vulnerabilities and insecurities that add layers to his persona, making him more relatable to the audience. This narrative shift offers a rare glimpse into the consequences of Charlie's lifestyle choices, encouraging viewers to empathize with him as he faces the repercussions of his actions.

16 "Go Get Mommy's Bra"

Season 2, Episode 4

One of the best Two and a Half Men season 2 episodes provides some insight into how Charlie and Alan are the way they are, as Evelyn is revealed to be as much of a pleasure seeker as Charlie. Evelyn has sex in Charlie's car, but she leaves behind her expensive bra, which leads to an awkward confrontation between the two. Revelatory moments, like finding their mother's undergarment, provide context for their absurd present-day dynamics. "Go Get Mommy's Bra" gives audiences a deeper understanding of why the Harper brothers are the way they are.

The discovery of Evelyn's bra in Charlie's car becomes symbolic, peeling back layers of the characters' histories and providing insights into their relationships and behaviors. This episode cleverly uses humor to address deeper issues of family influence and the cyclical nature of behavior ed down through generations. It highlights how Evelyn's actions and attitudes towards relationships have significantly shaped Charlie and Alan's views on love and life.