Two and a Half Men was arguably one of the biggest, funniest, and most successful comedies of the entire 2000s, not only establishing a firm cult-like fan-base despite Charlie Sheen's off-camera antics, but being nominated for several prominent awards throughout its historic run.
Season three was just a taste of what was to follow when it came to the Harper Boys (Charlie, Jake, and Alan) as they continued their hysterical Malibu beach-house antics in season 4.
10 Repeated Blows to His Unformed Head, Episode 7 (8.0)
In this particular episode, audiences got introduced to Naomi, Berta's youngest daughter who was about 8 months and 29 days pregnant. Alan develops a keen interest in her as it's revealed he has a fetish for pregnant women, meanwhile, Berta and Charlie confront the man who got Naomi pregnant and end up coaxing $5000 0ut of him. When Berta and Charlie return home, they discover Naomi in labor and rush her off to the hospital... where after the pregnancy is over she admits that the man Berta and Charlie shook down couldn't possibly be the father.
9 My Damn Stalker, Episode 15 (8.0)
Rose is known throughout the series as being Charlie's crazy stalker who lived just two doors down and had spent four seasons trying to creepily convince Charlie that they were destined to be together. So when Rose announces that she is moving to London, Charlie thinks it's just another scam to try and win him over. Rose says her goodbyes to everyone (with Charlie still not buying it) and gets in a cab to head to the airport. Charlie goes to close her open front door... and notices all of her furniture and belongings are gone and realizes she actually left for good.
8 Who's Vod Kanockers? Episode 2 (8.0)
Season 3 of Two and a Half Men ended on a major cliffhanger when Charlie and Mia separated because she wanted Alan to move out. So a couple of episodes into season 2 when Alan tells Charlie he was an idiot for letting her go, Charlie informs him that the reason why they broke up was because of him, prompting Alan to launch into a string of guilt-riddled favors for his brother. After a hilarious confrontation with a guest appearance from Steven Tyler, Charlie finally admits to Alan that he got cold feet about his wedding and used Alan as an excuse for backing out.
7 Release the Dogs, Episode 8 (8.1)
In this episode, Alan hasn't been able to sleep for several nights and has tried every remedy (besides pills) to fix the problem and finally goes to a psychiatrist to talk through the problem.
She helps Alan realize that his brother's success might be causing his resentment (which is causing his lack of sleep) and Alan has to figure out how to resolve it. Meanwhile, Charlie goes back on his word with a deal he made with Jake, resulting in Jake pranking Charlie in a string of events that leads to him getting attacked by police dogs on the beach, which is all Alan needed to help him get to sleep.
6 Smooth as a Ken Doll, Episode 19 (8.2)
The nineteenth episode of season 4 introduced Myra, the sister to Judith's new husband, Herb, as she was in town getting ready for their wedding. It's clear Judith and Myra do not get along so Myra tags along with Charlie, Alan, and Jake for the day and ends up staying at their house in order to steer clear of Judith. By the end of the episode, Myra ends up on Charlie's bed and the two spend the night together, which can be overheard by Alan and Jake in the room below.
5 Anteaters. They're Just Crazy Lookin', Episode 23 (8.2)
When Charlie falls through the broken deck and they have to hire somebody to fix it, they end up hiring a young, handsome handyman who has a beautiful singing voice and is essentially just a younger version of Charlie. That's why it's understandable that Charlie got upset when the handyman, Fernando, ended up stealing Charlie's girlfriend away from him. Charlie humbly accepts that it makes sense that his younger girlfriend should date a younger better-looking guy, until he tells his girlfriend that he'll buy her expensive jewelry and wins her back, then proceeds to fire Fernando.
4 Aunt Myra Doesn't Pee A Lot, Episode 20 (8.3)
The episode the followed the introduction of Myra followed Judith and Herb's actual wedding day and dealt with the aftermath of Charlie and Myra sleeping together. Charlie somehow ends up making it into the row of groomsmen while Alan gets confronted by Herb's ex-wife who tries to sleep with him in the coatroom of the church.
Myra reveals to Charlie in the middle of the ceremony that they shouldn't stay in contact after the wedding due to the fact that she's married, while Alan ends up ruining the wedding entirely when he refuses to sleep with Herb's ex which results in her causing an embarrassing (and hilarious) scene.
3 Apologies for the Frivolity, Episode 6 (8.4)
The premise of this episode revolved around the fact that Charlie was dating a woman who was a carbon-copy of his own mother. They had the same job, wore the same clothes, had the same number of children, and had the same emasculating and demoralizing personalities. However, Charlie doesn't see it and has to be informed of the truth by everybody else in the series. Alas, he still won't believe them and invites Lydia and her children over - only to see how Lydia treats her children exactly how Charlie's mother treated him and Alan as kids (a.k.a. horribly) and it finally clicks in Charlie's brain what's going on. He responds appropriately - and then doesn't.
2 Prostitutes & Gelato, Episode 24 (8.4)
The season 4 finale introduced Teddy, Evelyn's new boyfriend, who was incredibly wealthy and asked Charlie and Alan to come with him on a spontaneous trip to Vegas to watch a boxing match. The guys both tag along and while the fight is a let down (K.O. in 17 seconds) they all still have a good time gambling - until Teddy pulls out a ring and informs the boys that he wants to marry their mother and wants their blessing. The boys are hesitant at first, but they let down their defenses when Teddy buys them time with prostitutes and gelato.
1 Walnuts & Demerol, Episode 11 (8.7)
In one of the most memorable holiday episodes that Two and a Half Men ever produced, Charlie found himself throwing an unwanted Christmas party when a multitude of people show up at his house, start drinking, and simply don't leave. An assortment of characters make appearances (Rose, Judith, Evelyn, Herb, Berta, Kandi) and they all mingle and enjoy the party together, while Charlie takes his date upstairs to 'ring in the new year'. However, he gets interrupted by his mother who tells him that he can't sleep with his date because it turns out she might be his (**gasp**) half-sister. Charlie immediately gets out of the bed and Berta and Rose praise Charlie finding his sexual boundary as a Christmas miracle.
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