12 Most Rewatchable Episodes Of Two And A Half Men

Like a laugh factory, "Two and a Half Men" cranks out the chuckles for 12 seasons. However, you'll be hard pressed to find anyone who prefers the Ashton Kutcher era over the Charlie Sheen epoch. So much so that the most rewatchable episodes all come from when Sheen's Charlie Harper ran wild on the show. It's only the truth, because if someone ranks the funniest moments from "Two and a Half Men," no one thinks of Kutcher's Walden Schmidt as being a part of anything particularly hilarious.

Created by Chuck Lorre and Lee Aronsohn, the side-splitting sitcom sees high-strung cheapskate Alan Harper (Jon Cryer) move in with his rich, womanizing brother Charlie after his divorce. Alan's young son, Jake (Angus T. Jones), also spends a lot of time at Charlie's Malibu beach house; the trio gets up to all forms of mischief and encounters a variety of wacky characters along the way. In the ninth season, after the presumed death of Charlie, billionaire Walden Schmidt buys the Malibu home. Not much changes as Alan befriends and mooches off Walden — much like he did to Charlie before.

Let's take a look back at the (mis)adventures that continue to tickle the soles of our sense of humor to this very day. Here are the 12 most rewatchable episodes of "Two and a Half Men."

The first season of "Two and a Half Men" paints Alan as being rather unlucky in love and romance. He struggles to meet women, turning out to be the polar opposite of Charlie. When he does receive the rare opportunity, it usually falls apart in a comical way, such as in "Sarah Like Puny Alan."

The episode sees Charlie looking forward to a date with his neighbor Kathy (Lori Lynn Lively), so he tells the flu-ridden Alan to not spread his germs around the house. Kathy suggests Charlie bring someone along for a double date with her sister Desiree (Johanna Black), so Charlie tells Alan to get better and join them. Alan is reluctant, because he feels unwell and thinks Charlie wants to set him up with the "uglier" sister. Yet, when Alan finds out that Desiree is a famous soap star, he and Charlie work overtime to get Alan to feel better. In the end, Charlie becomes sick too, and both brothers miss out on the double date.

Throughout the entirety of "Two and a Half Men," Charlie establishes himself as a germaphobe, so it's cackle-worthy to see how he treats Alan, fearing that he'll catch whatever he has. Ultimately, he does. It's also impossible to not laugh at the extent to which the brothers go so that they can attend the double date rather than reschedule. They fail, and it's all down to their inability to be honest with their dates.

Compared to Charlie, Alan is a modern-day saint. However, in "The Price of Healthy Gums Is Eternal Vigilance," Alan comes to believe that he's been repressing a darker personality, which he dubs "Bad Alan." After his mother, Evelyn (Holland Taylor), brings up a Silly Putty shoplifting incident from Alan's youth that he has always denied, Alan confesses to Charlie that he thinks he did it, but he blocked the incident out of his mind for self-preservation. Since then, he's been on guard to avoid "Bad Alan" coming out ever again. Little does Alan know that it was Charlie who planted the Silly Putty on him.

To hear Alan talk about himself as if he's Luke Skywalker being tempted by the dark side and resisting its pull is hilariously ridiculous, since no one believes this about him for a single second. Eventually, when Charlie comes clean to his brother, Alan's over-the-top reaction proves equally priceless. 

The worst part of it? When Alan forces Charlie to tell the truth to Jake, since he doesn't want his son to see him as a criminal, Jake compliments Charlie on framing Alan. Bad Alan? It's more like "Poor Alan" here, as everyone giggles at his misfortune.

Despite their differences, Charlie and Alan view their mother, Evelyn, through the same lens. They see her as manipulative, unkind, and judgmental, leading her to damage and traumatize those whom she comes into contact with. In "Squab, Squab, Squab, Squab, Squab," Evelyn becomes jealous after hearing that Jake spent time with his other grandparents, so she demands a sleepover at her place. Both Charlie and Alan fear for Jake's wellbeing but fold in the end, bribing him to spend time with his grandmother. What transpires is that Jake bests Evelyn through acts such as spitting out the food she serves him and even flooding her home. It's to the point that Evelyn can't wait to get rid of him.

The exchanges between Jake and Evelyn turn out to be pure comedy gold. While she throws passive-aggressive jibes at her grandson about his lack of etiquette, Jake seemingly doesn't care. The funniest part is when she asks him if he eats squab. Jake has no idea what it is, but he loves the sound of the word and repeats it over and over again, much to Evelyn's chagrin.

A fun fact about "Two and a Half Men" that most fans might not know is that Blythe Danner actually played Evelyn in the original pilot but was replaced by Holland Taylor. Judging by Taylor's comedic chops and chemistry with the cast, especially in this electric episode, it proved to be a wise choice.

Charlie dates a variety of women throughout the show, so it was bound to happen that he would meet a dangerous person at some point. In Season 3's "Hi, Mr. Horned One," Charlie starts seeing the eccentric and spooky Isabella (Jodi Lyn O'Keefe). Alan expresses his concerns about Isabella, resulting in him developing a swollen eye that he believes is due to a curse she placed on him. Isabella's true interest in Charlie is finally revealed after she and her coven try to force him to give up his soul to Satan. Who saves him here? Evelyn, whom Isabella and her cult fear and know all too well somehow.

"Hi, Mr. Horned One" operates like a gender-swapped sitcom version of "Rosemary's Baby," as Charlie gets preyed on by a cult. Yet, even throughout this ordeal, he never appears to be fully aware of what's going on around him, thinking it's some kind of hedonistic game. That's what makes it zanier: Everyone worries about him, except for Charlie himself.

The cherry on top is how the cult dreads Evelyn, implying that she might be the Devil herself, or at least one of the Horned One's minions. Considering how Charlie and Alan speak about their mother, this is even more perfect.

Even though Charlie prefers to chill out rather than work, he still has some semblance of professional pride in him. In "The Unfortunate Little Schnauzer," Charlie is nominated for an award because of a jingle he created; however, he doesn't want to go to the awards ceremony, since his biggest rival, Archie Baldwin (played by Jon Lovitz, who famously enjoys singing roles like his cameo in "The Wedding Singer"), always walks away with the big prize and boasts about it. After some coaxing from Alan, though, Charlie and his family attend the ceremony.

Lovitz and Charlie Sheen go toe-to-toe in this laugh-until-you-snort episode of "Two and a Half Men." Archie is such a smug and unlikable character who treats himself as a rock star among the jingle community. His little tunes are ridiculous, but they seem to engross the audience and anger Charlie, so mission accomplished.

Without question, the best moment in "The Unfortunate Little Schnauzer" is when Archie performs his jingle for the United Nations' orphan program, "Save the Orphans," at the awards ceremony. Yes, it's a completely silly singalong song and the lyrics are cringe-worthy and condescending about the plight of orphans, but that's the point. This catchy chorus worms its way into the brain, as even Charlie's own family waves their arms along with everyone else.

The saga of Alan and Kandi (April Bowlby) stands out as one of the best story arcs in "Two and a Half Men." Anyone with a set of eyes could see the pair wouldn't last too long, but Alan married her anyway. The relationship lasted a heartbeat, with them splitting up and leaving Alan in a similar situation as he had been with his first wife, Judith (Marin Hinkle).

In the Season 4 episode "A Pot Smoking Monkey," Alan and Kandi go through divorce proceedings, but Alan wants to fight for custody of their dog, Chester. Alan approaches Judith, looking for the number of the attorney who handled their divorce and ensured Judith got everything. However, Judith hits him with a truth bomb: She already referred Kandi to the same lawyer. When Alan tries to talk to Kandi, he discovers that she and the attorney are in a sexual relationship. Feeling out of options, he decides to dognap Chester.

It's easy to see where this episode leads in the end, but that doesn't stop it from being a total rib-tickler. A desperate Alan does desperate things, much to the amusement of the audience and horror of Charlie, who finds a giant dog in his house. The final scene of Chester sitting on the couch with Alan, Charlie, and Jake remains a legendary shot from the show.

Ever heard the adage that men marry their mothers? Well, Charlie proves that it isn't too far from the truth in the highly rewatchable episode from "Two and a Half Men" Season 4, "Apologies for the Frivolity."

The plot follows Charlie as he dates a woman named Lydia (Katherine LaNasa). Almost immediately, everyone notices how similar Lydia is to Evelyn, especially in terms of her bossiness, cruelty, and manipulative nature. It takes a while for Charlie to see the same thing everyone else does; however, he can't seem to quit Lydia, even after his housekeeper Berta (Conchata Ferrell) threatens to resign after Lydia's treatment of her. For some reason, Charlie is addicted to Lydia.

It's hysterical to see how Lydia's two young sons resemble miniature versions of Charlie and Alan, and how watching Lydia meet Evelyn for the first time is like them looking in the mirror. Of course, "Apologies for the Frivolity" is an allegory for all the mommy issues that Charlie has, but that doesn't prevent it from turning into a priceless episode that gets funnier with each rewatch. If a "Two and a Half Men" reboot ever materializes, the lesser-celebrated scene-stealer Lydia needs to be a part of it too.

A recurring gag in "Two and a Half Men" revolves around how cheap Alan is. He never wants to pay for anything, always trying to get others to cover his bills and lifestyle. Clever on his part, irritating to others whom he mooches off.

In "Corey's Been Dead for an Hour," Charlie grows annoyed by his brother's stinginess. It all starts when Alan claims to have forgotten his wallet when he goes to the movie theater with Charlie and Jake. Later in the evening, during a double date, Alan retreats to the bathroom to avoid picking up the check. This leads to a standoff and then a fight between the brothers, until Charlie finds out that Alan has $5,000 in cash hidden in his bedroom. This discovery leads to Charlie devising the ultimate payback.

It's karmic justice when Charlie discovers Alan's money and spends it freely by tipping an outrageous amount to the pizza delivery guy. Watching Alan squirm is even funnier, because he initially doesn't want to come clean to his brother about his savings since he's been sponging off Charlie for so long. Finally, he does, and his reasoning surprisingly makes sense to anyone who watches the show. The flash-forward sequence at the end is also brilliant, showcasing Alan's fear actually coming true as he's forced to work alongside Jake at the movie theater concession stand.

Alan's biggest frustration with Charlie is how he seemingly stumbles into success without much effort. Case in point: the Charlie Waffles persona. 

"Is There a Mrs. Waffles?" demonstrates how Charlie turns into a superstar among kids and parents after releasing children's songs about seemingly inane subject matter. Charlie rides the wave of popularity and fame as Charlie Waffles, even though he has almost zero passion for what he does. There's only one issue: Charlie has never performed in front of a large crowd, so he develops stage fright as a huge concert looms. How does Charlie cope? Oh, that's easy — the same way he deals with his other issues in life: he drinks the problem away.

Considering what everyone knows about Charlie's bad behavior on the show and how he's the furthest thing from a role model, it's amusing how he finds success with the younger audience. Also, there's nothing sincere about Charlie Waffles, but he milks it for every cent it's worth and even tries to pick up the children's mothers in the process. On the other side of the coin is Alan, who is jealous of how the universe favors his low-effort brother. Can anyone blame him for his bitterness?

The "Two and Half Men" Season 5 episode "Fish in a Drawer" could be considered a TV crossover you had no idea happened, even if it's rather subtle. For this episode, the writers of "CSI: Crime Scene Investigation" swap places with the scribes from "Two and a Half Men." A few familiar faces from the popular crime show, such as George Eads and Jamie Rose, even appear here as well.

This murder-mystery themed instalment of the sitcom turns into a riotous affair, as the story is all about the murder of Teddy Leopold (Robert Wagner), who had just married Evelyn. It's Charlie and Courtney (Jenny McCarthy), Teddy's daughter, who find Teddy's body in a compromising position, leading to a whole lot of questions about who could have done it. In typical "Two and a Half Men" style, it never turns away from the outlandish humor or commentary, even in the interrogation scenes.

The revelation of who Teddy really is continues to be a fresh twist to this day and never feels telegraphed on the show. For a while, the showrunners had everyone believing that Teddy could be a good husband to Evelyn, as well as a desperately needed father figure for Charlie and Alan. Alas, it wasn't meant to be.

Charlie's promiscuity catches up with him, especially with the revelation of his illegitimate daughter, Jenny (Amber Tamblyn), in the seasons after Charlie Sheen's firing from "Two and a Half Men." Yet, a similar premise is explored earlier in the Season 6 episode "Taterhead Is Our Love Child."

During an outing, Charlie, Alan, and Jake bump into Chrissy (Rena Sofer), whom Charlie dated years earlier. With Chrissy is a little boy named Chuck (Aaron Refvem), who looks remarkably like Charlie, dresses like him, and is likewise a piano prodigy. Plus, he's around the same age as when Charlie and Chrissy would have last been intimate. All signs point to the obvious, right? Initially, Charlie doesn't think so, but after some convincing from the others, he comes around to the idea that he might be Chuck's father and wants to be there for the kid.

As revealed at the end of the episode, Chuck isn't Charlie's son at all. It's all part of Chrissy's clever ruse to extract money from Charlie. Even so, it's comical to watch Charlie go from denial to acceptance about the boy. As a matter of fact, it's even a little heartwarming to see Charlie dreaming about all the quality father-son time that he and Chuck could spend together in the future.

The seventh season of "Two and a Half Men" features an overarching storyline where Charlie becomes serious with Chelsea Melini (Jennifer Bini Taylor). While Charlie goes steady here, he still does foolish things that could split them apart. This leads to the lie he tells Chelsea in "Yay, No Polyps!"

Chelsea pressures Charlie to meet her parents; however, Charlie doesn't want to do it. So, he fibs to Chelsea, telling her that he has a colonoscopy appointment. His plan almost falls apart after Chelsea insists on going to the clinic with him. Well, she calls his bluff and reveals she knew he was lying all along, so he's forced to undergo it anyway. What's even worse is Charlie discovers that Chelsea invited her parents over to Charlie's home, which negates the whole need for a colonoscopy. Matters take yet another unexpected turn when Chelsea's father, Tom (Stacy Keach), makes racist comments then drunkenly admits his romantic feelings for his Black friend Ed, resulting in Chelsea's parents splitting up and Tom finding true love.

"Yay, No Polyps!" is a highly rewatchable episode of "Two and a Half Men" because it plays out like a domino effect, with Charlie's lie leading to a host of events that might not have happened otherwise. Also, the fact that Charlie was actually willing to go through a colonoscopy to not meet Chelsea's parents is both hilarious and sad at the same time.