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The hit CBS sitcom Two and a Half Men may have come to an end back in 2015, but it featured so many memorable characters and hilarious storylines that it remains pervasive in pop culture seven years after its conclusion. Of course, every sitcom has its holiday episodes, and Two and a Half Men is no exception. From Thanksgiving to Valentine’s Day to Christmas, the show covered it all.
The escapades of Charlie Harper and later Walden Schmidt may not have exactly been relatable, but, alongside everyman Alan Harper, the Two and a Half Men crew endured the trials and tribulations of their complex social lives, something to which viewers may well have connected. Much of their social mishaps occurred during or because of big holiday gatherings, meaning that major holidays were an important part of the series’ plot.
Updated on May 18th, 2022 by Tanner Fox: Though it has since been eclipsed in popularity by series like The Big Bang Theory and Black-ish, Two and a Half Men has yet to leave the public consciousness despite its cancellation more than half a decade ago. Controversial thanks to its raunchy subject matter and thanks to one-time star Charlie Sheen, it was certainly one of the strangest sitcoms of the 2000s and 2010s.
Perhaps there was something oddly endearing about the kinship between Alan, Charlie, Jake, Berta, and the revolving cast of characters who came into their lives. Alternatively, it could have been how tragically relatable their holiday gathering fiascoes were.
11 Family, Bublé, Deep-Fried Turkey (Season 12, Episode 8)
The final season is rich with holiday episodes, and this final Christmas episode touches upon all of the traditional troubles one would expect to see in Two and a Half Men. All Walden wants is to get little Louis to believe in Santa, but Evelyn and Alan get in the way.
This cringy and frustrating episode is a perfect holiday mess that’s bound to make viewers laugh, but still not one of the best this show has to offer. Unfortunately, the twelfth season was one of the series’ lowest-rated, and this is reflected in “Family, Bublé, and Deep Fried Turkey.”
10 Advantage: Fat, Flying Baby (Season 10, Episode 13)
Walden assumed a false identity to begin dating a woman named Kate so that he could be sure that his romantic partner loved him for his personality and not his money. However, this backfires, as Kate is insulted when Walden reveals the truth, opting to break up with him.
In this episode, Kate makes plans to return to spend Valentine’s Day with Walden, but she reveals that she’s still not interested in him. Debuted on February 14, 2013, it’s just another example of Walden’s incredibly tumultuous love life, and fans more or less considered it to be a mediocre installment in Two and a Half Men’s tenth season.
9 The Ol’ Mexican Spinach (Season 12, Episode 1)
In the premiere of the show’s final season, Halloween and fall are in the air. While Walden is dressed as zombie Elvis, he has a cardiac scare that puts him in the hospital.
As it turns out, this spooky holiday leads to a total existential crisis for Walden, and he begins to consider adopting a child. It’s a ridiculous episode, but it does have a zombie Elvis and a Ferris Bueller. Plus, it adds a dramatic flair to proceedings, something that’s necessary to break up the monotony of a below-average sitcom season.
8 Give Santa A Tail-Hole (Season 10, Episode 11)
Out of all of the Christmas-themed episodes in Two and Half Men history, this may be the most joyous. While masquerading as an average joe, Walden takes on a job as a tree salesman to buy his girlfriend a new sewing machine. Meanwhile, he and Billy argue about selling to Zuckerberg for half a billion dollars. Plus, Alan is all alone at the beach house where chaos obviously ensues.
Tech conglomerates and social media moguls are constantly in the news these days, proving that, though it ended seven years ago, Two and a Half Men remains surprisingly relevant. Plus, it’s one of the most sincere episodes in the history of the series, something fans didn’t get much of during the Charlie Sheen era.
7 Santa’s Village Of The Damned (Season 3, Episode 11)
Throwing it back to season three, this Christmas was spent with Charlie, Alan, and Alan’s romantic fling Sandy. Sandy had an almost zealous interest in Christmas, going all-out when decorating the house and getting upset when her reindeer figurines aren’t aligned properly.
This complicated holiday is definitely not one fans would like to have themselves, but it’s certainly entertaining to watch it go down in the Harper household. It’s a quintessential earlier episode of Two and a Half Men full of all kinds of yuletide chaos.
6 One False Move, Zimbabwe! (Season 9, Episode 12)
In this episode, Walden’s mother arrives to spend Christmas. Of course, Alan can’t help but be totally head over heels for her. On a more ridiculous note, Alan learns that Walden used to have an unusual pet.
With Walden on a downward spiral and Alan smitten with his friend’s mother, things get pretty cringey pretty quickly, and it’s a typical example of how easily things can spiral out of control in Alan’s life.
5 Warning, It’s Dirty (Season 7, Episode 11)
This episode has a lot of holiday love, and, while it takes place on Christmas, there isn’t a ton of holiday cheer. Evelyn is dating a dirty-minded old guy in a wheelchair, and Charlie tries to get Jake to hook up with a pretty girl since his girlfriend is away.
There’s a lot of classic Charlie Harper and womanizing in this episode, and it doesn’t really work out for anyone, but it’s still a hilarious holiday celebration. Plus, it’s a pretty good example of what the show was all about when Charlie Sheen was its star.
4 Sips, Sonnets, And Sodomy (Season 9, Episode 16)
It’s Valentine’s Day, and Alan and Walden find themselves stuck at home with both Lyndsey and Zoey because of a torrential storm. To make it worse, the ladies are definitely not getting along.
This episode is hilarious and full of some pretty ridiculous fights, and it works as a more realistic depiction of what Alan’s odd living situation might bring about. It’s not exactly the most memorable episode of Two and a Half Men, but, given the tumultuous love lives of Walden and Alan, a Valentine’s Day wrought with cabin fever could have gone no other way.
3 On Vodka, On Soda, On Blender, On Mixer! (Season 11, Episode 10)
This Christmas episode is all about Walden and Jenny as the former helps the later score a second date with a woman she’s interested in. Alan has his own interesting love affair, and there’s a lot of caroling to be had.
This episode didn’t earn many positive reviews, but it’s definitely a fun holiday episode with a lot of cringe and humor, and it still has fans laughing enough to remember and love this episode.
2 Merry Thanksgiving (Season 1, Episode 10)
In the first season of the series, Charlie Harper tries to impress an old flame during the holidays. On Thanksgiving, he invites—actually, “bribes” would be a more appropriate term—all of his family members to come over for a fancy dinner.
Of course, nothing goes as planned, and there are feuds and secrets in every corner. Every fan loves the mess that is the Harper family, so there isn’t a dull moment. It’s a quintessential early episode of Two and a Half Men.
1 Walnuts And Demerol (Season 4, Episode 11)
This might just be the most memorable Two and a Half Men holiday episode, and it certainly deserves some love. All Charlie wants is a date and some love to celebrate Christmas Eve, but he can’t seem to stop everyone from showing up at his house.
From Herb, Evelyn, and Judith to Berta, Alan, Kandi, the Harper house is filled with holiday spirit… and some pretty ridiculous and uncomfortable conversations. This episode represents Two and a Half Men at its best, and it’s yet another example of Charlie and Alan damaging their social statuses by way of a holiday happening gone very wrong.
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