After over 31 seasons The Simpsons has amassed plenty of Christmas episodes, with an impressive seventeen Christmas specials in the long history of the animated sitcom. After over 30 years on the air, the anarchic animated family comedy The Simpsons has somehow only aired five Thanksgiving specials throughout its 700+ episodes.
The Simpsons have a much more regular track record when it comes to the spooky season, having aired regular Halloween episodes every year since their second season. However, there’s another major holiday that The Simpsons has an uneven track record with, having barely mentioned it during the show’s first ten seasons, but constantly dwelled on it at any opportunity ever since.
There are no less than seventeen Christmas episodes starring Springfield's favorite family, an impressive lineup that includes some late-season classics, some vintage early gems, and admittedly a few later-season duds as well. At 31 seasons The Simpsons have a few more Halloween Treehouse of Horror specials than Christmas episodes, but with seventeen Yuletide installments aired already and another on the way next month, Christmas is quickly catching up.
“Simpsons Roasting On An Open Fire”
Not including the Tracey Ullman short “Simpsons Christmas,” The Simpsons began their history of Christmas specials at the very beginning of the series itself. The first-ever episode of The Simpsons is a Christmas special entitled "Simpsons Roasting On An Open Fire", which sees a down-on-his-luck Homer attempt to earn, win, or otherwise find enough money to afford some solid gifts for his kids. As that synopsis hints, it’s a pretty dark outing filled with the cynical humor of early Simpsons seasons but with none of the later zaniness to soften the heavy atmosphere. But this darkness makes the denouement, where Homer gets Santa’s Little Helper for the kids, all the more heartwarming.
“Marge Be Not Proud”
The Simpsons’ second holiday outing came in season 7, during what is typically regarded as its golden age. Although this era is famous for mile-a-minute gag fests such as "Cape Feare," the surprisingly poignant "Marge Be Not Proud" is a more sentimental episode that sees a penitent Bart try to make up for stealing Bonestorm. Of course, this being The Simpsons, there are still countless classic jokes from “THRILLHO’ to Lee Carvallo’s Putting Challenge, and the episode balances laughs and sweetness thanks to inspired moments like Bart’s heartfelt gift to Marge.
“Miracle on Evergreen Terrace”
One of the darker Simpsons Christmas outings, "Miracle on Evergreen Terrace" sees Bart accidentally burn the family’s presents, only to try lying his way out of the problem and accidentally causing all manner of trouble with Springfield’s too-generous townspeople. In typical Christmas tradition, the story is all about self-realization and the value of being true and moral over the holidays, which lasts until pretty much the very next episode for Bart. So it's hardly a Scrooge-style revelation.
“Grift of the Magi”
This goofy episode from season 11 features one of The Simpsons' greatest cameos from Gary Coleman, and the critically well-liked episode doesn't disappoint either. This outing uses the then-recent Furby craze to satirize the commercialization of Christmas and the state of the US education system as a toy company buys Springfield Elementary and starts using the kids to focus group their latest product. It’s a mile-a-minute episode which sees The Simpsons at its zaniest and also boasts cameos by Tim Robbins and Clarence Clemons.
“Skinner’s Sense of Snow”
A classic in the vein of “Das Bus,” “Lemon of Troy,” or “Wild Barts Can’t Broken,” season 12’s “Skinner’s Sense of Snow” makes the canny choice to disregard Springfield’s adult population for the bulk of its brisk runtime. Most of the episode focuses on the kids running wild after being snowed in with Skinner over the holidays, and this critically well-liked Simpsons installment mines humor from Skinner’s attempts to control the kids, their eventual takeover of the school, and Ned and Homer’s misadventures attempting to save them.
“She Of Little Faith”
Season 13 saw the arrival of American Hustler star Richard Gere in Springfield, and not a moment too soon since the family's resident conscience Lisa was undergoing a crisis of faith. This is the episode in which Lisa converts to Buddhism and, as well as some moving family moments and thoughtful social satire about the commercialization of Christmas, there’s also an inspired opening riff which sees Bart try to send a hamster to space and end up inadvertently turning Springfield's house of worship into a Mr. Burns-sponsored megachurch.
“’Tis the Fifteenth Season”
The Simpsons' riff on How The Grinch Stole Christmas is a well-liked episode by and large, but the Claymation segment truly shines in this season 15 outing. Once more, this is a Christmas Carol riff as Homer realizes the error of his ways and sets about making himself the nicest man in town, before the eventual epiphany that he needs to steal Christmas in order to make everyone happy (thanks to some accidental meddling by Lisa). Interestingly, this is also only the second time Lisa's Buddhism is mentioned after its debut in the equivalent episode of the previous season.
“Simpsons Christmas Stories”
The first Christmas anthology episode from The Simpsons, this outing manages to cram a retelling of the Nativity, a stellar Burns/Grandpa/Santa wartime adventure, and an inspired riff on The Nutcracker into its tight runtime. While anthology episodes can often be used to cover a lack of ideas, this one actually won its screenwriter awards attention.
“Kill Gil, Volumes I & II”
Uniquely mean-spirited, this odd season 18 outing sees the ever-unlucky Gil lazing about the titular family’s home when he overstays his welcome one Christmas. The dark ending is misjudged, but it’s hard to dislike an episode that gave viewers the “Grundle,” a bizarre Grinch knock-off.
“The Fight Before Christmas”
With a trio of quick-moving segments featuring live-action Simpsons puppets, a Katy Perry cameo, an inspired Martha Stewart riff, and a parody of The Polar Express, this busy season 22 episode feels more like a "Treehouse of Horror" outing than a Christmas special (which is actually a good thing).
“Holidays of Future Past”
Critically adored, this Christmas-set season 23 outing was originally intended to be a Simpsons series finale, and it shows. The sweet, sincere episode is funny, clever, and filled with satisfying pay-offs for characters both major and minor and it's one of the most satisfying of the show's many trips into the future.
“I Won’t Be Home For Christmas”
A surprisingly sad outing from The Simpsons’ season 26, “I Won’t Be Home For Christmas” sees Homer leave his family alone for Christmas as he’s convinced his presence is a burden. This one has a sweet It’s a Wonderful Life-style pay-off and played well with critics and audiences upon release.
“White Christmas Blues”
Disliked by critics, this season 25 outing turns the Simpsons' family home into a B+B for demanding tourists in a thinly-plotted episode. While some of the jokes landed, the episode largely felt like a collection of disparate parts that didn't quite fit together properly - a larger issue with how more recent seasons have been written.
“The Nightmare After Krustmas”
This fast-paced season 28 outing fits parodies of every holiday institution from Frozen, to Bing Crosby, to Jesus himself, into a Krusty-centric Christmas special. Focusing on Krusty made for a breath of fresh air (particularly because he's one of the best supporting characters in the entire show) and the frequency of successful jokes is very much more in line with earlier seasons than more recent.
“’Tis the 30th Season”
Another Christmas episode featuring a conflict between Marge and eternal loser for Gil Gunderson (bizarrely), this cynical outing worked thanks to its dark, sharp sense of humor and subversion of family sitcom conventions. Unfortunately, for some the heavy focus on those sitcom conventions made for a stark reminder that The Simpsons is at its best when it is aspiring to be something more than that.
“Bobby, It’s Cold Outside”
In this recent festive offering, Sideshow Bob attempts to give up his life of crime and vendettas (once again) in a critically middling but undeniably fast-paced outing from season 31 (the first of no less than three Christmas airing in one year). Sideshow Bob is a smart character to trot out for a special episode thanks to Kelsey Grammar's performance, and this one relies heavily on him to lift it out of the usual doldrums.
“The Way of the Dog”
With Cate Blanchett and Austin Powers actor Michael York as guest stars, this season 31 finale may have aired in mid-May 2020 but the episode is set at Christmas and features frequent flashbacks to the very first episode of The Simpsons. Revisiting the story of Santa’s Little Helper decades later, this was ultimately a sweet end to an uneven season.