It’s hard to think of an animated series that’s more iconic than The Simpsons and for over three decades and 700 episodes, it’s remained a touchstone of the industry. There’s still no end in sight for the classic animated series and at this point, it’s easy to joke that the series might not actually ever end.
The latest seasons of The Simpsons may not be as representative of groundbreaking adult animation as its golden years are, but there’s still a lot of enjoyment to get out of the series. The Simpsons has tackled practically every topic imaginable at this point, but one area that they handle especially well are their various holiday-themed installments.
10 "Skinner's Sense Of Snow" Celebrates The Chaos Of Winter Break And The Holiday Season
"Skinner's Sense of Snow" is a bright spot from season 12 of The Simpsons. It's a more subdued holiday installment that's focused on the general trappings of winter rather than Christmas in particular. Bart, Lisa, and the rest of Springfield Elementary, including Principal Skinner, get locked into school over winter break due to an unruly snowstorm. "Skinner's Sense of Snow" doesn't take itself too seriously and the episode excels because of its character dynamics, whether it's Homer and Flanders, who come to the rescue, or Skinner's low-status role as his students humiliate him and hold the educator hostage.
9 "'Tis The Fifteenth Season" Teaches Homer An Important Lesson
Part of the reason that The Simpsons perseveres for so long is because the characters all remain in some level of stasis. In this sense, Homer is always expected to be lazy and unintentionally negligent, but "'Tis the Fifteenth Season" sees the stubborn character get overcome with some inspirational holiday spirit. Homer takes advantage of a game of Secret Santa and becomes vilified, only to see the errors of his ways and attempt to show the community how much he cares. "'Tis the Fifteenth Season" borrows from both A Christmas Carol and How The Grinch Stole Christmas.
8 "Grift Of The Magi" Has The Perfect Mix Of Absurdity And Corporate Criticism
Season 11’s Christmas episode, “Grift of the Magi” is a good reflection of the increasingly broad sensibilities of The Simpsons the longer that it’s on the air. “Grift of the Magi” features rebellious Furby parodies and a karate-performing Gary Coleman, yet it still manages to be a Simpsons episode that’s sweet and satisfying.
“Grift of the Magi” actually has some worthwhile points to make about the commercialism of the holiday season and many of the set pieces with the Funzos are ridiculous in the very best kind of way.
7 "Homer Vs. The 18th Amendment" Is A St. Patrick’s Day Episode With Bite
When it comes to Simpsons holiday episodes it's easy to overlook "Homer vs. The 18th Amendment" even though it's from the animated comedy's sweet spot in season eight. The episode begins with St. Patrick's Day festivities, which is a rarity for the series, and this public display of embarrassing drunken behavior results in Prohibition hitting Springfield. Homer's emergence as the Beer Baron and his feud against Rex Banner is hard to top and there’s actually an important message about alcohol and freedom of speech buried deep down in this episode, too.
6 "Treehouse Of Horror VI" Marks The Very Best Of The Series’ Halloween Anthologies
The Simpsons has turned seasonal anthology horror into a yearly tradition with its annual "Treehouse of Horror" Halloween special and this entire list could be filled with episodes purely from this subset of episodes. Many of the earlier "Treehouse of Horror" offerings are excellent with no weak stories, but "Treehouse of Horror VI" is especially impressive. Springfield's war against giant corporate mascots and a Nightmare on Elm Street-inspired riff with Groundskeeper Willy are just inspired, but in terms of innovation, "Homer3" marks a genuinely exciting moment for the series as it plays with different media.
5 "Bart Vs. Thanksgiving" Reflects The Series’ Contemplative Earlier Seasons
It's fascinating to consider how much The Simpsons has evolved and the series' first two seasons are very different in some respects. "Bart vs. Thanksgiving" is a season two installment that centers around the sibling rivalry between Bart and Lisa over the Thanksgiving holidays.
Its stakes are technically quite small, but it sends Bart down a reflective journey where he actually learns quite a bit and grows closer with Lisa and the rest of his family as a result. The Simpsons' series premiere is a touching holiday installment, but "Bart vs. Thanksgiving" accomplishes even more.
4 "I Love Lisa" Is The Simpsons’ Pristine Take On Valentine’s Day And Young Love
The Simpsons devotes a lot of attention to Christmas and Halloween, but there's an inherent level of emotion to Valentine's Day that's made it an important anchor to some of the strongest holiday episodes. "I Love Lisa" goes all the way back to season four and it tells what's arguably the best Ralph Wiggum story in an episode that provides the boy a surprising amount of depth and also teaches Lisa a very important lesson in the process. There's a reason that "I Choo Choo Choose You" still has meaning nearly three decades later
3 "Miracle On Evergreen Terrace" Turns The Simpsons Into Holiday Pariahs
The Simpsons is at its best when it digs deep into both the dysfunction as well as the loving bond between the titular family and few holiday episodes do this better than season nine's "Miracle on Evergreen Terrace." The episode features a simple lie that snowballs out of control and suddenly Bart's accidental destruction of his family's Christmas presents turns into a city-wide act of kindness with major ramifications. The episode both separates and unites the Simpsons in a strong story that's also just as effective as an episode about the power of Springfield's community.
2 "Marge Be Not Proud" Is An Emotional Juggernaut About Guilt And Disappointment
At its very best, The Simpsons turns out some incredibly powerful emotional episodes that helped cement the series’ status as an all-time classic. An extremely powerful Christmas episode is season seven’s “Marge Be Not Proud.” Bart gets caught shoplifting and it causes a brutal rift between him and his mother that eats away at him more than it does at Marge. Bart and Marge episodes are few and far between and this is easily one of the best. It tells an important story, but it’s also full of classic jokes, many of which revolve around ‘90s video games.
1 "Holidays Of Future Passed" Is A Love Letter To The Generational Gift Of The Simpsons
"Holidays of Future Passed" is from The Simpsons' 23rd season, long past its glory days, but this Christmas-centric entry turns out to be surprisingly emotional and would function as a perfect series finale if it didn't already happen. Various Simpsons episodes have turned the clock forward, but none are as comprehensive as "Holidays of Future Passed," which doesn't just introduce new Simpsons grandchildren, but also a respectful Bart and wistful Homer that exhibit fantastic character development. The episode has a lot of hyperbolized fun with this distant version of the future, but it’s an episode where humanity comes first.