Two And A Half Men Funniest Moments Ranked

"Two and a Half Men" was a sitcom about rich bachelor Charlie Harper (Charlie Sheen) and his brother Alan (Jon Cryer), who moves into Charlie's house along with his son Jake (Angus T. Jones) after a messy divorce. At first, Charlie is reluctant to burden his carefree single life with family members. 

But over time Charlie grows to acknowledge, rather begrudgingly, that he has come to like Alan and Jake's presence in his house and his life. The show aired on CBS for twelve massively-successful seasons from September 22, 2003, to February 19, 2015, with Charlie getting swapped out for Walden Schmidt (Ashton Kutcher) after the eighth season after the handsome young billionaire comes to own Charlie's house and becomes friends with Alan.

Although the series tried to march on without Charlie, it was clear that his absence had drastically affected the dynamic of the main cast. When it was firing on all cylinders, "Two and Half Men" could be relied upon to deliver a barrage of uproarious one liners, and the chemistry between Sheen and Cryer and the rest of the cast elevated such comedic moments to even greater levels. Here are 14 of the best comic moments that "Two and a Half Men" presented audiences with over the years.   

In the episode "Ergo, The Booty Call" (Season 3, Episode 16), Charlie, Alan, and Jake are having a meal together when Alan's gorgeous-but-dim girlfriend Kandi (April Bowlby) decides to drop by. Jake hears Kandi tell Alan that she wanted to surprise him with a "booty call," and he asks Charlie to explain what the term means. 

Never one to pass up an opportunity to embarrass Alan, Charlie encourages Jake to ask his father about the phrase. Jake goes to Alan in front of Kandi and bluntly asks him what "booty call" means. Feeling awkward but trying to spare Jake's innocence, Alan attempts to deflect by saying Kandi said the phrase in connection to laundry. But Charlie continues to needle the situation.

This launches Alan deeper down the rabbit hole, as he comes up with a convoluted explanation about how old-timey cowboys would call out "Booty! Booty!" to people before cleaning their clothes in rivers wearing nothing but boots. Alan's desperate improvisations, coupled with Charlie's deadpan questions designed to make the situation even more awkward, are hilarious to watch. Especially when Kandi throws cold water on Alan's whole subterfuge by asking when the phrase started meaning "casual sex." 

Charlie Harper is shown to live a pretty blessed life in that he has no responsibilities, makes a lot of money simply by writing jingles, and sleeps with a parade of beautiful women. But amidst all the debauchery, Charlie does feel something real is missing from his life. This feeling was exacerbated in "Rough Night in Hump Junction" (Season 5, Episode 15).

Unfortunately, Charlie's response to the feeling of emptiness was to launch himself into a series of desperate flings. A lot of the women that Charlie sleeps with turn out to have boyfriends and husbands. Throughout the episode, we see Charlie opening the door to large men, only for them to lay him out with a punch. 

In a hilarious inversion of Charlie's "cool" persona, we see him hanging around his house with two black eyes and a bloody nose. He is also forced to use a donut pillow to soothe his lower half after an unfortunate adventure with a girl in the bedroom. In the end, Charlie has to come to terms with the fact that this self-destructive cycle of affairs will not bring Mia, the love of his life, back. 

Alan has a tortured relationship with his ex-wife Judith (Marin Hinkle). She is shown to despise his guts, but the two are forced together due to their joint custody of Jake. What really boils Alan's blood is the alimony checks that he has to give to Judith every month, even though his own circumstances are far from stable. 

That was why he was thrilled to hear that Judith was finally getting married again in "Smooth as a Ken Doll" (Season 4, Episode 19). With great excitement, Alan wrote the very last check that he would ever have to give to Judith. Charlie did one better by stopping at a copier place to turn the ordinary-sized check into a giant one, much like those that game shows often use.

Alan's plans for a satisfying moment of handing the giant check to Judith appeared ruined when he went to her house and discovered she was having a big fight with her future husband. Alan tried to pour oil on troubled waters, even as he handed a normal-sized check to Judith. But despite the gravity of the situation, Alan could not resist quickly posing for a picture of himself handing the check to Judith, with an equally-oversized grin and a thumbs-up.  

While Charlie lives a blissfully contented life, that bliss is occasionally marred when he comes across a woman he has spurned in the past. Considering the number of women Charlie has slept with, it's a pretty long list. One of them happened to be Jake's ex-teacher Miss Pasternak (Alicia Witt), who made an appearance in "A Jock Strap In Hell" (Season 6, Episode 5).

While shopping at a drugstore for a new jockstrap for Jake, a woman spots Charlie and incredulously calls out his name. Charlie's impulse is to look around and mutter, "Where? He owes me money." But it's of no use. Alan and Jake recognize the woman as Miss Pasternak, Jake's old teacher. That is when it dawns on a horrified Charlie that he had previously slept with and then ghosted Miss Pasternak. 

Any hope that the incident might be dealt with tactfully goes out the window when Miss Pasternak starts screaming at Charlie that she gave her body and soul to him, and he treated her like garbage. Turns out that after Charlie dumped Miss Pasternak, she had a nervous breakdown, lost her job at the school, and was forced to start a new career as a stripper. The scene ends with Charlie beating a hasty exit, while Pasternak screams that he has ruined her life. Considering Charlie's prompt exit strategy, you can tell this was not his first time dealing with such a situation.   

In a lot of ways, Kandi was the best girlfriend Alan ever had. Sure, he had frequent bouts of insecurity over how she was way out of his league. But unlike all his other girlfriends, Kandi was sweet and encouraging towards Alan and considered him a catch. One thing that Kandi could not do, however, was provide Alan with intellectual simulation — a point made painfully, hilariously clear in Episode 14 from Season 3.

Alan is stung by the accusation that he is only dating Kandi for her body. To prove that he and Kandi have more in common, Alan attempts to have a serious conversation with her. It does not bode well when Alan finds Kandi engrossed in Jake's video games. She then asks him if he wants to have sex. Over the course of several awkward minutes, Alan tries to get to know Kandi better and learn more about her hobbies, like reading.

After it becomes clear that Kandi's idea of literature is reading billboards, her text messages, and menus, Alan tries to tell her about his own failed marriage and how it affected his mental health. Kandi's only response is to advise Alan not to tell people that story, because it makes him sound like a loser. Alan realizes that a deep conversation with Kandi isn't possible, and he resigns himself to another round of mindless sex instead, to which Kandi responds with a relieved, "Finally!"

Guest cameos by celebrities on sitcoms can often be a decorous affair. The celeb walks on to the set to huge applause, trades witty rejoinders with the main characters, and leaves. When Steven Tyler of "Aerosmith" fame cameoed on "Two and a Half Men," things went a bit differently. 

It was previously established that Tyler had rented a house near Charlie on the beach. In "Who's Vod Kanockers?" (Season 4, Episode 2), Charlie is struggling with the fact that he gave up a lifetime of happiness with Mia, and is stuck living with Alan forever. To make matters worse, Tyler can be heard singing at the top of his lungs at all hours from the house next door. At first, Tyler and Charlie have a verbal sparring match, with Charlie telling Tyler that fans only "tolerate" him playing the harmonica, to which Tyler responds by calling him a "lame ass jingle writer."

But soon, the conflict escalates into a physical fight ... which Charlie loses, badly. In the end, we see Charlie being driven home from the hospital wearing a neck brace and a bandage over his nose. Alan sums up the whole situation by remarking, "Well, the dude may look like a lady, but you fight like a little girl."

If not for Alan and Jake, Charlie's entire life would be a drunken orgy that he has trouble remembering later. Like in the Season 8 premiere "Three Girls and a Guy Named Bud." We see that Charlie spent a drunken night sleeping on the stairs of his house without pants, and cannot remember how he got in that condition. 

Later, Berta enters with Charlie's pants, which had been stuffed into the mailbox. The mystery further deepens when it is revealed that the back of the pants had been covered with postage stamps. Although still baffled, Charlie muses, "I must have had a plan of some kind." Later, Jake confirms that he had seen Charlie sticking the stamps on his pants, but experience had told him not to question Charlie's drunken actions.

The mystery is finally solved when Charlie finds a note that he had stuffed into the pocket of his pants before mailing them last night. The note reads, "Dear Inspected By Number 94 ... it is with a heavy heart that I write to you. The zipper you signed off on has snagged my ball sack. Thank you for your prompt attention to this matter. Sincerely yours, Charles Francis Harper."

The fact that Charlie was a complete horndog had been repeatedly emphasized throughout "Two and a Half Men." Following Charlie Sheen's exit from the show, Charlie Harper's funeral in the season 9 premiere "Nice to meet you, Walden Schmidt" only served to further highlight his horndog tendencies, since most of the women in attendance were ex-lovers who had only come to make sure Charlie really had died, likely hoping to spit on his grave.

At first Alan attempts to keep things civil by stating that it is a sad day for all of them. To that, the response he gets is "Speak for yourself." Over the next few minutes, the female attendees list the many diseases they contracted after sleeping with Charlie. His mother was also too preoccupied with selling Charlie's house to properly grieve for her son. 

In the end, we get to hear from Rose (Melanie Jayne Lynskey), Charlie's wife at the time of his passing. It is strongly indicated that Rose had been responsible for Charlie's demise after finding him with another woman, to which Berta (Conchata Ferrell) dryly remarks, "Never cross a crazy woman."  

Between Alan and Judith (and Charlie as a frequent babysitter), Jake had little chance of growing up without warped views on sex and relationships. While staying at Judith's house, Jake hears her getting intimate with her new husband Herb (Ryan Stiles) in "Don't Worry, Speed Racer" (Season 4, Episode 13).

This leads to Jake asking Alan and Charlie how smart a person has to be to have sex. It turns out that Judith likes to give Herb detailed instructions in the bedroom, and that made Jake think you need a lot of brains to be good at that particular activity. 

As Charlie and Berta try to offer helpful advice, Alan keeps shutting them down. But Alan's own attempts to explain the matter to Jake don't end well, because the conversation keeps getting sidetracked to the subject of pie. The entire scene is a perfect example of how funny "Two and a Half Men" was in its prime, thanks to the chemistry between the original cast and the way they were able to adeptly bounce lines off each other.

Doctor Linda Freeman (Jane Lynch) was one of the funniest characters on "Two and a Half Men." Although she started out treating Jake for mental issues relating to his parent's divorce, it soon became her job to apply her psychiatric expertise and dry wit to the task of untangling the many, many emotional issues plaguing Charlie and Alan as well.

In "My Doctor has a Cow Puppet" (Season 1, Episode 22), we find Alan in the throes of suppressed agony over his relationship with ex-wife Judith. He starts sleepwalking, overreacts to minor incidents, and is clearly suffering. Charlie takes Alan to Dr. Freeman, who suggests that Charlie should pretend to be Judith, and Alan should confront Charlie/Judith about his feelings. 

The tactic works a little too well — particularly when Freeman hands Alan a padded baton. Charlie's taunting of Alan as Judith finally goads him beyond the breaking point. Soon, Charlie is seen cowering on the floor while Alan repeatedly hits him with the baton. Meanwhile, Freeman is standing over them, screaming at Alan to hit him harder. That scene remains one of the best examples of the complicated relationship between Charlie and Alan.

You can't begin to explore the psychological disarray of the Harper brothers Charlie and Alan without talking about the mother who made them this way, Evelyn (Holland Taylor). We've only ever seen glimpses of what Evelyn was like to a young Charlie and Alan, but their upbringing sure did a number on them that has affected their approach to women for the rest of their lives. 

We get a particularly hilarious example of this in "Apologies for the Frivolity" (Season 4, Episode 6). Charlie introduces the others to the latest woman he is dating, named Lydia (Katherine LaNasa). The only problem is, the others immediately see what Charlie doesn't. That Lydia is the spitting image of Evelyn. It is also clear that Charlie's attitude to Lydia is creepily similar to that of a child towards his mother. That, you know, he's sleeping with.

Things take a turn for the hilarious when Lydia comes face-to-face with Evelyn. The two have a catty-snippy verbal duel for the ages, at the end of which they both turn on Charlie. Hilariously, Charlie still refuses to see the similarities between the two, until he sees Lydia harassing her little sons in exactly the same manner as Evelyn once did with him and Alan.

In a house full of men, Berta the housekeeper was easily the most manly character. Blunt, sarcastic, and unwilling to back down in front of anyone, not even her employer Charlie, she would become a standout character on the show — essentially, an honorary fourth man. 

It is the others who are careful to stay on Berta's good side for fear of her temper. Which is why it was all the more hilarious to see Berta being scared of someone in "Hi, Mr. Horned One" (Season 3, Episode 6). 

The episode sees Charlie dating yet another new girl, this time named Isabella (Jodi Lyn O'Keefe). It soon transpires that Isabella is part of some kind of a sinister cult that appears to dabble in dark magic. At first, Charlie refuses to believe that there is anything wrong with Isabella, even though a host of bad things happen to the Harper household in her presence.

Berta is unimpressed when Alan tells her about Isabella. But then the two women come face to face. Immediately, Berta starts packing up her things to leave the house. When Alan asks her why, she exclaims, "You gotta put a whole lot of gone between you and a broad like that."

Despite all the issues surrounding their mother and women in general, Charlie and Alan are not the most mentally unstable people in "Two and a Half Men." Rose wins the title of "Biggest Nutcase" quite handily, which is ironic considering she has a Master's Degree in Behavioral Psychology from Stanford University.

Rose was introduced as Charlie's neighbor that is stalking him after a one-night stand. Over time, Rose's obsession grew to scary, hilarious lengths. In "Ergo, The Booty Call" (Season 3, Episode 16), Rose reveals that she has started dating a man named Gordon (J. D. Walsh).

Whatever kind of a man Gordon had been before, it is immediately apparent that Rose wants to turn him into Charlie 2.0, and she dresses him accordingly. Gordon says that sometimes Rose screams Charlie's name during sex, and sometimes she makes him say it. Despite the oddities of the situation, Gordon appears to have accepted his role as a Charlie substitute in Rose's eyes, since at one point he is seen trying to copy the way Charlie stands, to help further the illusion for Rose's sake.  

It would be difficult to pin Alan's many failings on one particular bad aspect of his personality, but one of the most prominent ones is his legendary cheapness. This is something that Charlie usually has to contend with, and most times, he lets it slide because he knows he makes a lot more money than Alan.

But one time, in "Corey's Been Dead for an Hour" (Season 4, Episode 9), Charlie was determined to make Alan foot the bill for once. Charlie and Alan had gone on a double date, and Alan was trying to find a way out of paying for his half of the date. At first, Alan excuses himself to go to the men's room when it is time to pay the bill.

But Charlie follows Alan into the restroom. For the next few minutes, Alan desperately tries to stall for time while Charlie stays relentlessly on his tail. They pee together, wash their hands together, and when Alan bolts into a toilet stall, Charlie takes up a post in the next cubicle. After all that effort, Charlie is incensed to discover their dates have left with another man, while Alan is overjoyed to learn the man paid their check.