Two and a Half Men was great, at least for a while. The show follows a carefree bachelor living in Malibu whose debauched life gets disrupted by the sudden arrival of his recently divorced younger brother and his 10-year-old son. Two and a Half Men lasted twelve seasons, although it changed protagonists in Season 9 and descended into self-parody by its final season.
The show had a loyal following due to its recognizable comedy style full of sharp zingers, outrageous physical comedy, and relatable situations. That said, it was also criticized due to its outdated humor, misogynistic moments, and quality drop after Charlie Sheen left. Still, during its heyday, the show produced several stellar episodes. Funny, biting, and utterly unforgettable, the best Two and a Half Men episodes capture this essence, prompting fans to rate them highly on the popular entertainment site IMDb.
10"An Old Flame with a New Wick" (Season 1, Episode 18)
IMDb Rating: 8.4/10
The Season 1 episode "An Old Flame with a New Wick" features special guest star Chris O'Donnell. The plot focuses on Bill, a former flame of Charlie's who transitioned, taking the notorious bachelor by surprise with his good looks and winning personality. To complicate things, Bill starts dating Evelyn (Holland Taylor), much to Charlie's discomfort.
"An Old Flame with a New Wick" hasn't aged great. It might be one of the funniest Two and Half Men episodes, but its depiction of a trans man is not the best despite O'Donnell's best efforts. Still, Evelyn, ever the progressive and bold one, doesn't overreact to Bill's secret, although she does have a visceral reaction to learning he slept with Charlie. The humor is also never at Bill's expense and mostly focuses on the awkwardness of Charlie's ex dating his mother.
9"Hi, Mr. Horned One" (Season 3, Episode 6)
IMDb Rating: 8.4/10
"Hi, Mr. Horned One" is among Two and a Half Men's most memorable and funniest episodes. It revolves around Isabella (Madeline Zima), Charlie's most recent fling, who might be a Satan worshipper planning to use the debauched musician in a ritual.
Two and a Half Men goes all-in on Isabella's demonic proclivities, implying she curses Alan and sucks Charlie's life; she even scares Berta (Conchata Ferrell), which is no easy feat. The episode ends with Isabella leaving after realizing Evelyn is Charlie's mother. The implication is that Evelyn is a high-ranking member of Isabella's coven and maybe one of television's most powerful witches. It's an unusual move, made much funnier by the fact it never comes up again throughout the show, although Isabella returns twice in later episodes.
8"The Mooch at the Boo" (Season 6, Episode 9)
IMDb Rating: 8.5/10
The late Michael Clarke Duncan guest stars in the Season 6 episode "The Mooch at the Boo." The plot centers on Charlie bonding with his new neighbor, an NFL player whose daughter disappears with Jake (Angus T. Jones). Elsewhere, Alan uses Charlie's Mercedes to secure a date.
There are so many things that make the beloved comedy show's episode "The Mooch at the Boo" work. For one, Duncan has excellent comedic timing and instant chemistry with Sheen. The two create an uncomfortable yet funny dynamic that brings the best out of Sheen's abilities as a physical comedian. In typical Alan fashion, his story is annoying and pitiful, but Duncan single-handedly elevates the episode to new and impressive heights.
7"Is There a Mrs. Waffles?" (Season 5, Episode 8)
IMDb Rating: 8.5/10
"Is There a Mrs. Waffles?" sees Charlie earn unprecedented success as a children's singing star, Mr. Waffles, prompting Alan to descend into petty jealousy. The episode puts Alan through the ring but ends with the roles reversed as Charlie's recklessness catches up to him.
Despite being the show's deuteragonist, Alan is quite an unlikable television character. However, "Is There a Mrs. Waffles?" is among his best episodes, as the plot explores his feelings of inadequacy and envy for his irresponsible brother's effortless success. It's also nice to see Charlie brought down a bit, especially considering the show usually lets him get away with everything. The episode offered a deeper look at Charlie, which added complexity to his character without sacrificing the show's trademark laughs.
6"Walnuts and Demerol" (Season 4, Episode 11)
IMDb Rating: 8.6/10
Most sitcoms have holiday-focused episodes, and Two and a Half Men is no exception. Season 4's "Walnuts and Demerol" sees Charlie preparing for a steamy Christmas celebration with his date. However, his plans go south when his friends and family unexpectedly converge at his home and refuse to leave.
The Two and a Half Men episode throws a wrench in the perfect Christmas with unexpected guests and total chaos. Seldom did all the main characters from Two and a Half Men gather at once. "Walnuts and Demerol" features one such instance, with everyone, including Rose, meeting at the Harper house. The combination of so many chaotic characters makes for excellent comedy, with Charlie assuming the rare role of the straight man to everyone else's antics.
5"Gorp. Fnark. Schmegle." (Season 7, Episode 8)
IMDb Rating: 8.6/10
Charlie and Chelsea's relationship was arguably the best in the notorious bachelor's history. However, it isn't easy, largely thanks to Charlie's infamous ways. Still, he tries to stay faithful, and the Season 7 episode "Gorp. Fnark. Schmegle." proves it. The plot deals with a beautiful friend of Chelsea's staying at Charlie's home, making it hard for the well-known womanizer to keep his thoughts in check.
Two and a Half Men is among the most famous sitcoms with content that hasn't aged well and it probably wouldn't have been made today, especially regarding Charlie's behavior toward women. "Gorp. Fnark. Schmegle." finds Charlie on his best behavior - or as good as it can be. It's still creepy, but at least he realizes it and makes a conscious effort to tone it down.
4"Fish in a Drawer" (Season 5, Episode 17)
IMDb Rating: 8.6/10
CSI: Crime Scene Investigation is among the best procedural shows on television. Two and a Half Men satirizes it in the Season 5 episode "Fish in a Drawer," which follows a CSI team investigating Teddy's (Kevin Durand) sudden death during his wedding to Evelyn.
Written by CSI's writers and wearing the show's influence on its sleeve, "Fish in a Drawer" is among the all-time best Two and a Half Men episodes. Subversive, ridiculous, and surprisingly inventive, it perfectly uses its cast to tell a silly and endlessly hilarious mystery. Two and a Half Men never used the gimmick again, but perhaps they should have; "Fish in a Drawer" is a stroke of genius and one of the show's finest hours.
3"Camel Filters and Feromones" (Season 1, Episode 12)
IMDb Rating: 8.6/10
Transformers star Megan Fox guest-stars in the Season 1 episode "Camel Filters and Feromones." She plays Prudence, Berta's 16-year-old niece, working at the Harper house for the day and drawing unwanted attention from the three guys. Meanwhile, Alan attempts to convince Judith that Charlie's house is a good environment for Jake.
"Camel Filters and Feromones" has aged like milk. The story of two grown men setting their sights on a 16-year-old is inappropriate, to say the least. Rewatching it in 2023 feels weird, wrong, and uncomfortable, especially because most jokes focus on Prudence's desirability to the Harper brothers. However, it did elicit a lot of laughs and is a classic example of the show's ability to find humor in even the most cringe-worthy situations.
2"The Two Finger Rule" (Season 6, Episode 19)
IMDb Rating: 8.7/10
Michael Clarke Duncan returns to Two and a Half Men in the Season 6 episode "The Two Finger Rule." The plot sees Charlie, Alan, and Herb (Ryan Stiles) get drunk together after their stupidity leads to problems with their significant others. Soon, they are joined by Jerome and Gordon (J.D. Walsh), leading to a drunken support group.
"The Two Finger Rule" thrives on the chemistry between the guys. Herb is always a welcome and scene-stealing presence, and Duncan's Jerome fits seamlessly into the group dynamic. The episode is all about how their totally opposite personalities lead to hilarious misunderstandings. It's a shame this group never returned because their chemistry was great and could've been explored more.
1"Squab, Squab, Squab, Squab, Squab" (Season 2, Episode 23)
IMDb Rating: 8.7/10
"Squab, Squab, Squab, Squab, Squab" is arguably the funniest Two and a Half Men episode. The plot sees Jake spending a night with Evelyn while Charlie and Alan enjoy their free time at a bar. However, Evelyn gets more than she bargained for after she encourages Jake's culinary ambitions.
Taylor is a television icon and a comedic giant, and this episode features some of her best work in the 21st-century comedy show. She has excellent chemistry with Jones, and the plot allows her to display her physical comedy chops. This episode shows how funny it can be when someone super bossy lives with a kid who just says it how it is. Jake and Evelyn's odd-couple dynamic is also a prime source of laughter, especially considering how the episode ends.