The Simpsons is still running after decades and is often at its most sweet, scathing, and funny around Christmas.
While the better-known specials set around Halloween are the topic of more frequent conversations and carry more cultural cache, it is the moments in the winter that showcase the heart of the show. Here, we see the family being sweet, doing kind things for strangers, and learning a lesson or two along the way.
Of course, with more than 30 seasons to date it can be hard to pinpoint this content when wanting to watch it.
Thanks to us, readers will struggle with this no more. Below is our list of the best episodes of the show which take place at Christmas or have Christmas as a central theme. Some may not be seen as appropriate to include, but hey, if Die Hard can fuel endless debate about what it is or is not, so can this show about an animated typical American family.
10. “Simpsons Roasting on an Open Fire” (1989)
This episode started it all after Homer and the bunch’s roots with Tracey Ullman. Homer fails to earn cash for presents for the family after issues at work. Meanwhile, Marge uses what they have to remove a tattoo Bart got without permission, and, in a moment of desperation, heads down to the dog track. As a result, they meet Santa’s Little Helper, and he comes home to be a new addition. Homer is upset at first, but then his heart melts and he realizes the dog needs them as much as they need him — a nice message of family being found and good gifts really being free.
9. “Grift of the Magi” (1999)
‘Simpsons’ episodes after the 10th season often get stereotyped as being bad and unfunny, but that’s not the case here. A toy company buys the elementary school and privatizes it as a means of having access to the children for product development. When a toy called Funzo is released, the family resolves to steal it with the help of Homer. In the end we get a fun commentary on excessive commercialization and the presence of monopolies in so-called “family friendly” markets. A particular highlight is Homer breaking into numerous homes and overcoming obstacles.
8. “Holidays of Future Passed” (2011)
This episode gets included here for a number of reasons. For starters, it takes place in the future (this is always a great setting for the show), and features the family coming together for a Christmas holiday, while Bart struggles to be a better father to his sons and Lisa seeks to connect with her daughter. Seeing the pair discuss how hard it is to raise a young person right hits home around the holiday season. A fun fact is it was also intended as a series finale, too.
7. “Miracle on Evergreen Terrace” (1997)
As is the case with many episodes of the show, this one features Bart as its main focus and depicts what happens when he burns down the family tree and lies about it. Springfield and its kooky characters rally to their aid with a new tree and $15,000, but it is a bitter reward, after the incident that led to the fire is eventually revealed. The family is looted and in the end play with a tattered washcloth. The message here is you do not really need a lot at Christmas.
6. “Skinner’s Sense of Snow” (2000)
This episode of the show has the children trapped in school due to bad weather and makes our list because it touches on an aspect of the holiday season outside of the rituals and traditions people have known for centuries. When it comes down to it, school at this point of the year can suck. You watch a lot of dull movies, are ready for the holidays, and hate being there any longer than you have to be. Here, Principal Skinner tries to keep everyone under control but is soon overthrown and put through the ringer. It is fun to watch him get his comeuppance after so many prior moments of cold behavior.
5. “I Won’t Be Home for Christmas” (2014)
Let’s face it, a lot of holiday content ignores the darker side of what Christmas entails. This episode dares to go there. Homer stops in for a drink and Moe confides in him about how lonely and depressed he is and we eventually see how lost others can be. A modern classic and one which should get people thinking about others in need of kindness every single December.
4. “White Christmas Blues” (2013)
The main story in this piece has Springfield becoming a tourist hotspot due to being the only city in the nation to have snow at Christmas. This is fine and dandy, but the actual reason this episode is on our list is its side story. Lisa buys gifts for the family and is hurt when she sees Bart destroying his. However, she learns a lesson when he calls her out for getting gifts she would enjoy them having, not what they would actually like. This is a solid lesson to learn generally, and it says something about a cartoon that it can show it to viewers with a deft hand after decades of familiarity.
3. “She of Little Faith” (2001)
Lisa Simpson has arguably had the most growth throughout the show’s run and this is very much the case here. She loses her faith after the church becomes more commercial in its focus, finds solace in Buddhism after meeting Richard Gere, and learns from him it is okay to enjoy other holidays so long as you are secure in your beliefs and respectful of those who may have different ones. Her character arc is a great message of “peace on earth” that many could follow more often.
2. “Simpsons Xmas” (1988)
This was a short which aired on The Tracey Ullman Show, but is on our list as it is clever to see Bart’s take on the classic poem about the night before Christmas. It shows classics can be reworked to fit a modern context and correctly notes that parents get exhausted putting things together for their kids. It’s unfortunate more are not aware of it.
1. “Marge Be Not Proud” (1995)
Far and away, this is the best Christmas episode of The Simpsons to date. Here, Bart gets caught shoplifting a game Marge refused to buy him. He gets found out when the family returns to the store for their annual Christmas photo, breaks his mother’s heart, and in the end works hard to get back into her good graces. The story is capped off with her getting him a game he did not want, but he accepts it with grace, which displays his ability to grow as a person. So many holiday themes are present, and this episode should be standard viewing for anyone with a screen around the Christmas season.
The Simpsons is now available to stream on Disney Plus.
