25 Best Episodes Of Two And A Half Men, Ranked

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 supporting actors on the show, including Stiles, Michael Clarke Duncan, and J.D. Walsh.

The episode works perfectly because it includes some of the best supporting 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 support 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 passed 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.

15 “Nice To Meet You, Walden Schmidt”

Season 9, Episode 1

Marking a significant transition in the show, “Nice to Meet You, Walden Schmidt” introduces Ashton Kutcher’s late-addition Two and a Half Men character after Charlie is killed off at the very start of the episode. Heartbroken and suicidal, Walden buys Charlie’s house in Malibu, forging a bond with Alan in the process. This episode signified a new era for the show. The challenge of introducing a new main character was significant, but Walden’s debut was handled with a mix of comedy, sensitivity, and finesse. His endearing vulnerability makes him a character worth rooting for, something that Charlie wasn’t.

“Nice to Meet You, Walden Schmidt” stands as a pivotal episode not just for its narrative shift but also for how it manages to blend the legacy of Charlie Harper with the introduction of Walden Schmidt,

“Nice to Meet You, Walden Schmidt” stands as a pivotal episode not just for its narrative shift but also for how it manages to blend the legacy of Charlie Harper with the introduction of Walden Schmidt, creating a seamless transition that respects the show’s history while paving the way for new stories. Walden’s contrasting personality to Charlie’s offers fresh dynamics and comedic possibilities, and the bond that forms between Walden and Alan is particularly noteworthy; it redefines the show’s central relationship in a way that is both heartfelt and humorous.

14 “Just Like Buffalo”

Season 1, Episode 23

“Just Like Buffalo” is one of the first episodes to deal with Charlie’s negative influence on his nephew, Jake. Charlie has never really been a great role model, and this appears to be the case when he comments on “getting action” regularly and not needing a wife unless one has a sick desire to give away half of their possessions. Jake hears this and says it at his mother’s house in front of her support group. It’s one of the rare episodes where Charlie gets himself both in and out of a jam, showing his care for his family.

The episode provides comedic moments through Charlie’s usual antics and Jake’s innocent repetition of his uncle’s cavalier views on relationships, and delves into the consequences of Charlie’s influence on Jake. “Just Like Buffalo” uniquely highlights the complexities of familial relationships within the Harper household, demonstrating how Charlie’s offhand remarks can have a wider impact beyond his immediate circle. It’s a pivotal moment that showcases Charlie’s ability to navigate the messes he creates, not just for the laughs but also revealing a layer of responsibility and care for his family, especially his brother Alan.

13 “Does This Smell Funny To You?”

Season 2, Episode 24

Charlie’s propensity for womanizing gets him in trouble again, leading to some of the worst things Charlie did in Two and a Half Men. He has a fling with a much older woman, and this lands him in hot water with the woman’s husband, who comes to the house in search of her. As always, the consequences for Charlie are minimal, which doesn’t sit well with the uptight and moralistic Alan. It marries the series’ typical raunchy humor with a more complex narrative design, making for a standout episode.

“Does This Smell Funny To You?” encapsulates Charlie’s often controversial lifestyle choices and serves as a canvas to explore the dynamic and occasionally contentious relationship between him and Alan. The episode deftly uses its comedic premise to delve into deeper issues such as the consequences of actions and the varying moral compasses between the brothers. It’s particularly noteworthy for illustrating Alan’s constant tension and conflict towards Charlie’s escapades, juxtaposed with Charlie’s seemingly Teflon nature regarding repercussions.

12 Baseball Was Better With Steroids

Season 6, Episode 24

In one of the best episodes of Two and a Half Men, Alan and Charlie’s fiancée Chelsea are upset when Charlie’s ex-fiancée returns, and matters are made worse when Judith goes into labor while her husband Herb is incapacitated with a broken arm. It’s an excellent example of Charlie’s blasé attitude contrasting with Alan’s high-strung, nervous nature, and it’s made all the more memorable thanks to Herb, who makes ridiculous remarks while high on painkillers.

Ryan Stiles as Herb is hilarious as always, proving once more that he’s one of the best recurring Two and a Half Men characters. The contrast between Charlie’s carefree demeanor and Alan’s anxious disposition is at its peak, providing a fertile ground for both humor and character development. This episode exemplifies the show’s strength in balancing humor with the complexities of familial and romantic relationships, making it a highlight of the series.

11 “Hi, Mr. Horned One”

Season 3, Episode 6

“Hi, Mr. Horned One” takes Two and a Half Men into uncharted comedic territory, exploring the themes of superstition, influence, and the absurd through the lens of a devil-worshipping storyline. This episode showcases the series’ willingness to delve into wildly unconventional plots, bringing a fresh and eccentric twist to the sitcom format, as Charlie starts dating a comedically heavy-handed “Satanist” named Isabella.

Alan finds Isabella’s darkness and intense spirituality rather odd, and he encourages Charlie not to see her anymore, especially because Alan fears that she is a bad influence on Jake. Isabella puts a curse on Alan, and she and her friends drug Charlie and try to make him sell his soul to the devil. It’s an out-of-left-field episode, and a weird storyline that Two and a Half Men dropped. Nonetheless, Alan’s paranoia regarding the “curse” is hysterical.

10 “Three Girls And A Guy Named Bud”

Season 8, Episode 1

“Three Girls and a Guy Named Bud” stands out as a hallmark of Two and a Half Men’s comedic prowess, particularly in handling themes of teenage rebellion, parental mishaps, and the intricacies of unconventional family dynamics. This episode masterfully showcases the series’ ability to intertwine multiple comedic situations, leading to a crescendo of awkward and hilarious encounters that reflect the show’s signature humor. Here, Jake gets caught when two girls come sneaking out of his room at Charlie’s.

Alan gets caught in his own sticky situation when he comes sneaking out of Jake’s friend’s mom’s room, and Jake sees him.

Alan gets caught in his own sticky situation when he comes sneaking out of Jake’s friend’s mom’s room, and Jake sees him. Angered and upset that Alan is dating his friend’s mother, Jake decides to move in permanently with his own mother. However, at Judith’s, Jake gets caught once more when the same two girls appear out of his room. This premiere episode is the best episode of Two and a Half Men season 8, and one of the best of the series.

9 “Alan Shot A Little Girl”

Season 12, Episode 6

Not all the post-Charlie Sheen departure episodes are a letdown, as “Alan Shot a Little Girl” is one of the best Two and a Half Men episodes. Mrs. McMartin agrees to let Alan foster Louis for six months in preparation for adoption. However, Louis is a master manipulator, and Alan finds himself happy to give the kid whatever he wants, even if it means breaking one of Walden’s rules. Alan refuses to see the situation for what it is because he finally gets to be a cool dad. His constant attempts to gain Louis’ favor are over-the-top hysterical.

“Alan Shot a Little Girl” cleverly showcases a different facet of Alan’s character, exploring the lengths to which he will go to fulfill his desire for approval, especially in the wake of Charlie’s absence and the introduction of new dynamics with Walden and Louis. This episode stands out for its humorous take on parenting, adoption, and the challenges that come with attempting to discipline a child who knows how to work the system to his advantage.

8 “Can You Eat Human Flesh With Wooden Teeth?”

Season 2, Episode 16

One of the best episodes of Two and a Half Men has to do with one of the series’ main themes — parenting. Judith goes to Hawaii for a week, leaving Jake with Charlie and Alan. After Alan forgets to pick Jake up from school, he finds out that his work is being audited, and he needs Charlie on Jake duty instead. Charlie turns out to be a less-than-ideal parental substitute, combing Jake’s hair with spit, giving him frozen pizza, and dressing him in ridiculous outfits.

The running gag is that Jake keeps getting forgotten at school, and the same thing happens to Judith at the airport when she comes back from Hawaii. “Can You Eat Human Flesh with Wooden Teeth?” brilliantly encapsulates the chaotic yet endearing essence of the Harper family dynamics, particularly spotlighting the challenges and humorous mishaps of unconventional parenting. This episode provides a delightful exploration of Charlie and Alan’s attempts to manage their responsibilities towards Jake, with each brother bringing his own unique — and often hilariously inadequate — approach to childcare.

7 “The 9:04 From Pemberton”

Season 10, Episode 18

“The 9:04 From Pemberton” adeptly zeroes in on the minutiae of daily life — the humble toaster — to explore and expand upon the dynamics between Alan and Walden, showcasing how a simple domestic incident can escalate into an amusing saga that tests their friendship. Alan accidentally starts a kitchen fire while making toast, cutting the power and embarrassing Walden in front of his date. To make amends, Alan buys a new toaster, but Walden is utterly insulted by its low quality. This episode features some of the best moments in Alan and Walden’s relationship while highlighting all of Alan’s idiosyncrasies.

It’s a perfect example of one of the best episodes after Charlie Sheen left, as it shines in its portrayal of Alan’s well-meaning yet often misguided efforts to rectify his mistakes, set against Walden’s expectations and the reality of their living situation. The conflict over the toaster not only brings out the best comedic moments between the two but also serves as a metaphor for their relationship’s complexities and Alan’s struggle to find his place in a post-Charlie world.

6 “Is There A Mrs. Waffles?”

Season 5, Episode 8

“Is There A Mrs. Waffles?” showcases a unique facet of Charlie’s character, merging his typical womanizing ways with an unexpected venture into children’s entertainment as Charlie Waffles. Charlie had recently released a CD of original children’s songs under the lovable name Charlie Waffles, and he’s excited to learn that the new fame comes with attractive single moms and lots of money, making Charlie, for a time, one of the wealthiest characters on Two and a Half Men.

After signing some CDs and producing a commercial, Charlie’s manager sets up a concert for him. Charlie is hesitant, remembering how much stage fright he tends to get. Some songs, such as “Bye Bye Boobies” are hilarious in their own right. This episode cleverly utilizes Charlie’s newfound fame to explore themes of celebrity, the unexpected consequences of success, and the complexities of personal growth under public scrutiny.