1. “One Fish, Two Fish, Blowfish, Blue Fish”
This is the one where: Homer eats a poisonous fish and believes he only has twenty-two hours left to live.
Most tearjerking moment: In the middle of the night, Homer says goodbye to each sleeping member of his family and listens to an audio book of the Bible while he awaits death.
2. “Lisa’s Substitute”
This is the one where: Lisa falls in love with her charming, intelligent substitute teacher Mr. Bergstrom (voiced by Dustin Hoffman), only to be crushed when he leaves town for another job.
Most tearjerking moment: Before saying goodbye, Mr. Bergstrom hands Lisa a note, saying that if she ever feels alone and in need of comfort, the note will be all she needs. After he leaves, Lisa opens the note, which reads: “You are Lisa Simpson.”
3. “Bart Sells His Soul”
This is the one where: Bart, believing that there is no such thing as a soul, sells his to Milhouse for five dollars.
Most tearjerking moment: When Bart begins crying while praying for God to give him back his soul, and Lisa saves the day.
4. “Lisa on Ice”
This is the one where: Lisa and Bart join rival peewee hockey teams and must face each other in the championship game.
Most tearjerking moment: With the big game tied, Bart gets a shootout against Lisa, who’s in goal. Rather than having one of them win, both Bart and Lisa realize they love each other, drop their equipment and hug instead.
5. “Old Money”
This is the one where: Grandpa falls in love with a wealthy woman at his retirement home, but she dies suddenly, leaving Grandpa a large amount of money in her will.
Most tearjerking moment: After spending money on himself doesn’t cheer him up, Grandpa uses the inheritance to renovate the retirement home and name a wing of the building after Bea.
This is the one where: Homer becomes a genius after dislodging a crayon that’s been stuck in his brain since he was a boy.
Most tearjerking moment: After Homer’s had the crayon re-inserted to become “dumb” again, Lisa’s crushed. However, “smart” Homer leaves a touching note with the message above.
7. “Round Springfield”
This is the one where: Lisa befriends an aging jazz great named “Bleeding Gums” Murphy but is left heartbroken when he passes away.
Most tearjerking moment: When Bart uses the 500 dollars he won from a Krusty-O’s lawsuit to purchase Bleeding Gums’s rare album so Lisa can broadcast it on the local jazz radio station.
8. “Bart Gets an F”
This is the one where: Bart has to pass a history test or else he’ll repeat the fourth grade.
Most tearjerking moment: After studying harder than ever, Bart scores a 59 and still fails. Fortunately, while crying he spouts off some obscure historical trivia and Mrs. Krabappel bumps his grade up to a 60.
9. “Like Father, Like Clown”
This is the one where: Bart and Lisa try to reconcile Krusty the Clown with his father, Rabbi Krustofsky, who disapproves of Krusty’s career.
Most tearjerking moment: When Rabbi Krustofsky finally accepts his son’s profession and the two hug during a live taping of Krusty’s show.
10. “Dog of Death”
This is the one where: Santa’s Little Helper runs away after his expensive operation puts a financial strain on the Simpson family.
Most tearjerking moment: When Santa’s Little Helper, brainwashed to be one of Mr. Burns’s watchdogs, snaps out of attack mode and pounces on Bart, happy to be reunited with his best friend.
11. “Lisa’s First Word”
This is the one where: Homer and Marge tells the story of how Bart hated baby Lisa until her first word was her brother’s name.
Most tearjerking moment: It’s a toss-up between Lisa saying “Bart” for the first time, or the very final scene, when Maggie’s first word is “Daddy.”
12. “When Flanders Failed”
This is the one where: Flanders opens a shop for left-handed people and Homer spends the whole episode hoping it fails.
Most tearjerking moment: When the Leftorium fails and Flanders is forced to sell his house, Homer feels guilty and rounds up every single left-handed person in Springfield. They stop by the store and buy enough items to keep Flanders in business.
13. “Marge Be Not Proud”
This is the one where: Bart humiliates Marge by getting caught shoplifting a video game.
Most tearjerking moment: Either when Marge refuses to tuck Bart into bed at night, or this final scene, where Bart buys his mom a touching Christmas gift.
14. “Bart the Mother”
This is the one where: Beloved comedian Phil Hartman made his last Simpsons appearance voicing Troy McClure.
Most tearjerking moment: The “In loving memory…” title card shown during the end credits.
15. “Mother Simpson”
This is the one where: Homer is reunited with his mother, who he thought had died when he was a kid.
Most tearjerking moment: Wanted by the FBI, Homer’s mother goes on the lam and abandons Homer again. Rather than a funny button, the episode ends with Homer sitting on his cars watching the night sky.
16. “And Maggie Makes Three”
This is the one where: Homer tells the kids the story of Maggie’s conception, which was an accident, and how he and Marge adjusted to the surprise.
Most tearjerking moment: To feed three children, Homer literally crawls back to his old despised job at the nuclear plant. Mr. Burns hands him a plaque reading “Don’t forget, you’re here forever,” which Homer creatively edits using pictures of his beloved new daughter.
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