Celebrate 25 Years of The Simpsons with 25 Episodes That Go for the Heart
In its 25 years on TV, the cartoon family has given us some surprisingly human moments
Twenty-five years ago, the first episode of The Simpsons aired in the Sunday, 8 p.m., time slot that the show still occupies today and has for most of its quarter-century run. In the past 25 years, the show has generated laughs, riffed on countless pop culture sources, and even introduced whole words to our language.
However, The Simpsons has also had more tender, human moments than one might expect from a show starring cartoons with massive overbites. Check out 25 moments when the show reminded us that there’s some genuine heart beneath all that yellow.
In a flashback, Homer must return to his job at the power plant (which he quit in a spectacular fashion) when Marge becomes pregnant with Maggie. Mr. Burns punishes Homer with a plaque that reads “Don’t Forget: You’re Here Forever,” but in the final moments, it’s revealed that Homer has placed photos of his youngest child to make the sign read “Do It For Her.”
Substitute teacher Mr. Bergstrom (Dustin Hoffman) recognizes Lisa’s specialness in a way no one else ever has, and Lisa is heartbroken when he leaves. As his train pulls away, she reads the note he’s given her. It says, “You are Lisa Simpson.” As Lisa’s voice actor Yeardley Smith recalls, “What a glorious thing to say to a little girl.”
Bart gets caught shoplifting, but then gives Marge the best gift she’s ever gotten: A photo of himself, framed and paid in full, to make up for the fact that his larceny got him booted from the family Christmas portrait.
Bart blithely sells his soul to Milhouse and then desperately tries to get it back. Lisa buys it for him, but not before a rare, tense prayer session: “Are you there, God? I know I never pay too much attention in church, but I could really use some of that good stuff now.” Regardless of whether he actually lost his soul, this is the episode where he earns it.
The episode ends with Elizabeth Taylor delivering Maggie’s first word: “Daddy.” However, a beautiful bonding moment happens before that, when toddler Bart hears baby Lisa’s first word: “Bart.” He suddenly realizes how much his new sister thinks of him.
Homer is shocked to learn his mother, Mona (Glenn Close), is not only alive, but a fugitive from the law. By the end of the episode, she’s fled again. The credits run across Homer, sitting on the hood of the family car, looking at stars and pondering life.
The episode finds some dark humor in Maude Flanders’s untimely death by T-shirt cannon – Ned’s last words to her are “No footlongs,” after all – but it’s one of the few installments of TV to deal with death and how hard it can be to accept the sudden loss of someone you know.
A fortune teller tells Lisa the story of her first love, a very Hugh Grant-y British man (Mandy Patinkin) who ultimately leaves her at the altar because he can’t accept her boorish family. Lisa, however, leaves the renaissance faire hand-in-hand with Homer, because she knows she loves him for who he is.
Homer gives up drinking for a month. When his 30 days are up, he celebrates by eschewing the expected bender for one of the more romantic moments he and Marge have shared: Singing “Raindrops Keep Fallin’ on My Head” during a sunset bike ride.
No one signs Lisa’s yearbook. When she makes cool kids friends while the family is away for the summer, Bart gets them to fill up the blank pages with notes saying how much they’ll miss her (only after outing her as a nerd, of course). They also decorate the family car in seashells. Homer is less enthusiastic about this.
Homer tries sushi and ends up ingesting potentially deadly blowfish poison. He lives, of course, but there’s a moment in the morning when Marge sees him slumped in a chair and think’s he’s a goner. Julie Kavner’s pronunciation of “Homer” has never sounded more woeful.
Child Protective Services places the Simpson kids with a foster family that just happens to be the Flanderses. Everyone is aggrieved by the separation, but the sweetest moment happens when Maggie chooses the Flanders flock over Homer, Bart and Lisa – but then picks Marge over even the wholesome Flander crew. For a moment, you see how she sees her mom, and it’s in the most glorious light.
Lisa rushes to tell her saxophone idol, Bleeding Gums Murphy, about her successful school recital – only to find out that he passed away the previous night. Does it seem like an undue portion of heartache on The Simpsons happens to Lisa? It should. It does.
14. ‘The Way We Was’
In a flashback episode, we learn that Marge didn’t go with Homer to prom, but with Artie Ziff (Jon Lovitz), whose “busy hands” ruin the evening (and Marge’s dress). Later, when Marge picks up Homer, who’s walking in the mud, he finally gets to pin his corsage on her, fixing her broken dress strap. They’ve been together ever since.
It’s famous for being “the episode that Michael Jackson performed in under a pseudonym,” but it’s also one of the kindest moments Bart and Lisa ever share: Bart and the Simpsons’s houseguest (Jackson) surprise Lisa with a birthday song wishing her the best.
Homer gets the line of the episode when he comes to terms with his daughter’s decision not to eat meat: “I understand, honey,” he tells her. “I used to believe in things when I was a kid.” It’s quite bittersweet, when you think about it, but the subsequent piggyback ride into the sunset is sublime.
The show’s first-ever episode is a Christmas special that introduces Santa’s Little Helper, a one-time racing greyhound, with the line, “But he’s a loser! He’s pathetic! He’s a Simpson.”
18. ‘I Love Lisa’
Ralph’s brief infatuation with Lisa really makes you feel for the little dolt, but the most painful part comes when Lisa tells Ralph that she won’t be his girlfriend on live TV. Bart, of course, manages to pinpoint the exact frame in which Ralph’s heart breaks.
In one sense, it’s a sweet episode: You find out Ned Flanders and Mrs. Krabappel quietly got married some time ago. In another, however, it’s quite sad to watch it today, because the actress who voiced the character, Marcia Wallace, died in October 2013. The show has since retired her character, effectively making Ned a widower twice over.
20. ‘Old Money’
Grampa finds love at the Springfield Retirement Castle in Bea Simmons (Audrey Simmons), but she dies suddenly. Alone again, he finds that her $100,000 estate brings him no joy, but he finds purpose again in spending the money to improve the conditions of the retirement home.
In just the third episode of the show, Homer becomes so dejected after Mr. Burns fires him that he attempts suicide – even writing a suicide note that reads in part, “I only hope I can provide a better model in death than I did in life.” Marge and the kids rush out to literally talk him off a ledge.
Marge’s sister Selma desperately wants a husband and child. She’s even willing to endure a loveless marriage to actor Troy McClure. But when he asks her to give him a child to further his career, she realizes she has sacrificed too much and leaves it all – ultra-modern aquarium house included – in search of meaningful love.
Nelson Muntz goads Bart into shooting a bird, and Bart kills it (though he deliberately tries to miss). Bart is horrified, and when he finds eggs in the nest, he shows a remorseful side that turns into a maternal side.
Homer worries that an affair with sexy co-worker Mindy (Michelle Pfeiffer) may be inevitable, but once they’re alone in hotel room on a work trip, Homer realizes his love for Marge is stronger than temptation. True love triumphs, and then Homer sings her the best re-working of Barry Manilow’s “Mandy” ever.
Milhouse moves away and Bart turns to Lisa for friendship. When Milhouse returns, Lisa is bummed that the friendship is apparently over, but in the end Bart invites her to a special game of Monopoly where he’s made special chance cards – including the one Lisa acts on immediately, “Good for one hug.”
Play Kill, Bonk, Marry: ‘The Simpsons’ Edition
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