While the last four seasons (as well as Charlie Sheen’s off-screen antics) tarnish the memory of Two and a Half Men, audiences can often forget that this comedy about two brothers and their son/nephew living in Malibu was the routinely the most popular sitcom on television.
During season 6, the boys were still a few seasons away from Charlie’s blow-up and the complete overhaul of the series, and the show continued to produce just as many laughs as it had for the past half-decade.
10 Damn you, Eggs Benedict, Episode 3 (8.1)
Audiences got to watch little Jake grow up before their very eyes – and one step toward growing up is getting drunk for the first time. Jake asks his uncle if he can have a sip of his beer, to which Charlie replies no and tells him (sarcastically) that if he wants beer he should go ask a hobo outside a liquor store.
Unfortunately, Jake takes his uncle’s advice and has a homeless man buy him a beer, which Jake and his friend get efficiently hammered on. Meanwhile, Alan tries to play the field for the first time in his life by dating two women at once – and mucks up both relationships within a 30 minute span.
9 It’s Always Nazi Week, Episode 6 (8.1)
The series was never known for making any dramatic twists or turns (aside from Alan getting married in Vegas) but one of the biggest the show ever had came from this episode where Judith asks Alan to look after Jake for three consecutive months.
Alan and Charlie agree, but they also want to know why Judith wants this long break – it turns out, the break is because Judith and Herb are having marital problems and Judith kicked Herb out. A gleefully satisfied Alan goes over to Judith’s to rub her failed marriage in her face… only to wind up in bed with her.
8 Best H.O. Money Can Buy, Episode 7 (8.1)
The follow-up episode to the previous one where Judith split up from Herb and started dating Alan again, found the former married couple rekindling their relationship, but Alan is unsure whether or not he wants to continue. Meanwhile, a lonely Herb befriends Charlie and tries to become a womanizer like him, only to run away crying when Charlie buys him a hooker and declares he wants his wife back.
At the same time, Alan and Judith have a fight and realize they don’t want to be together. Herb and Judith decidedly get back together… only to announce six weeks later that Judith is pregnant with Herb’s baby (but Alan is pretty sure it’s his).
7 David Copperfield Slipped Me a Roofie, Episode 14 (8.1)
There were so many times throughout the series when Alan would get into a fight with Charlie and decide that he was moving out for good, only to come crawling back – this episode was no different. Alan’s new girlfriend Melissa sets up a surprise birthday party for him, but can’t believe the way that his family treats him while there.
Due to their disrespectful behavior, Melissa invites Alan to live with her instead. Alan accepts the invitation and initially, it’s great… until Melissa’s mother gets Alan stoned out of his mind and they wind up in bed together. Safe to say, Alan ended up back at the beach house.
6 Thank God for Scoliosis, Episode 12 (8.2)
Before Alan could move in with his girlfriend, he had to get his new girlfriend in the first place. It just so happened that his receptionist, Melissa, made it clear she was interested in Alan and the two couldn’t keep their hands off each other despite their professional relationship.
Alan eventually makes his way to Melissa’s house where he hopes to do the deed, only to be hindered by Melissa’s mother who ruins the mood by getting baked and showing Alan up-close-pictures of Melissa’s birth. Alan just can’t catch a break.
5 She’ll Still Be Dead At Halftime, Episode 16 (8.3)
One of the additions in season 6 was the character of Chelsea, Charlie’s only true serious girlfriend for the entire series, who goes away for a funeral during this episode, leaving Charlie alone for the first time in a while. Of course, that means that a beautiful, drunk, blonde woman from his past shows up on his front door and wants sex.
Charlie is going to oblige to the woman’s desires and invites her upstairs, only to realize he doesn’t want to betray Chelsea and stops himself. Unfortunately, he gets a call from Chelsea that she’s headed home (almost there, in fact) and the drunk horny woman has passed out on Charlie’s bed. Charlie, Alan, and Jake spend the rest of the episode trying to get the inebriated party-girl out of the house without Chelsea finding out.
4 Above Exalted Cyclops, Episode 21 (8.3)
Rose might have been a crazy stalker, but in her own special way she was a maniacal genius and she definitely proved it during this episode. Charlie had been dating Chelsea most of the season and she was beginning to feel bad that Alan didn’t have anyone to go out with, so she decides to set Alan up with one of her friends – which just so happens to be Rose.
Charlie and Alan are flabbergasted when they see Rose on the date, but they keep their mouths shut to keep Chelsea from finding out. Eventually, Rose and Alan start dating for real and Charlie knows it’s going to end poorly – which it does when Rose super-glues a model-car to Alan’s private parts.
3 Baseball Was Better With Steroids, Episode 24 (8.4)
The final episode of the season was so funny that it brought new life into the world – that is, in the form of Judith and Herb’s child when Judith goes into labor when she’s at Charlie’s house. Alan, Charlie, and Herb rush Judith to the hospital where they run into Melissa, Alan’s now ex-girlfriend after the in-bed-with-her-mother incident which causes problems of its own.
Judith is rushed to a room, but unfortunately, Herb keeps injuring himself when he tries to help her which leaves Charlie in charge of taking care of Judith. She eventually has a healthy baby girl (that looks like Alan).
2 The Mooch at the Boo, Episode 9 (8.6)
R.I.P. Michael Clarke Duncan. The episode that introduced the deceased actor as Charlie’s neighbor, Jerome Burnett, a retired football star, had the famous athlete at odds with Charlie when Jake goes on a date with his daughter, Celeste, and doesn’t come back by the agreed-upon time.
Meanwhile, Alan takes Charlie’s car to the shop for a tune-up and winds up attracting a young woman in the waiting room… only to have her play Alan for a fool and steal Charlie’s Mercedes in the process.
1 The Two Finger Rule, Episode 19 (8.8)
Every guy who’s been in a relationship has had a night like this. During this episode, both Charlie and Alan mess things up with their girlfriends and end up hanging out with each other. As it turns out, Herb gets into hot-water with Judith and joins them, and so does their new neighbor Jerome.
The four men are then joined by another sad-lonely-guy when Gordon, the pizza delivery guy, shows up with pizza and admits that his wife left him. The sad group decides to start singing show-tunes and talk about the nicknames that their ladies have for their private areas… which is the last straw for Charlie who finally goes to Chelsea and apologizes for the stupid thing he did.
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