Wait, this supposed to be a comedy? Oh right, it was created by the same guy who also has that show about the DOG THAT WAITED FOR FRY UNTIL HE DIED.
1. Season 7, Episode 11 “Marge Be Not Proud”
What’s Sad? Bart, televisions original “lil shit”, decides to steal a video game that his mother, Marge, refuses to get him. Marge is very disappointed to learn Bart has shoplifted when they return to the scene of the crime; a local store (Try-N-Save) where they typically get their Christmas picture taken. Needless to say, their Christmas photo is ruined. Concerned that his mom doesn’t love him anymore, Bart picks up something at the Try-N-Save and returns home. Fearing his son has shoplifted again, Marge forces the object out of Bart’s jacket, and discovers he has paid for a Christmas photo of himself as a gift to his mom.
Why The Tears? Bart’s “lil shit” badassery is put on the back burner in order to win back the affection of his mom. Who knew Bart was such a mommy’s boy after all? A heartwarming and touching episode that shows that sometimes a boy’s best friend really is his mother.
Fox
2. Season 1, Episode 1 “Simpsons Roasting on an Open Fire”
What’s Sad? I’m sorry, is this supposed to be a comedy show? Where we get to laugh and stuff? So why is the PILOT EPISODE on this list? Oh, I’ll tell you. After Homer doesn't get his usual Christmas bonus, the family scrambles to buy Christmas gifts. Homer, desperate for money, secretly takes up a mall Santa gig, and is revealed when Bart harasses him at work. Taking what little money he made at the mall, Homer bets it all on a 99-1 long shot dog, coincidentally named “Santa’s Little Helper”. The dog finishes dead last, Homer loses his money, big surprise. The dog’s owner disowns him after finishing so poorly, and Bart begs Homer to keep the dog as a family pet. In lieu of gifts, the Simpson family gets a dog for Christmas instead.
Why The Tears? This has all the classic elements of a tearjerking Simpson episode: Bart ashamed of his mistakes, Homer trying to provide for the family, and a heartwarming ending. Bonus because there’s a dog involved! This was one hell of a pilot episode!
Fox
3. Season 3, Episode 1 “Stark Raving Dad”
What’s Sad? This is a very complicated episode to explain, so I’ll cut to the meat of it. After spending some time in a mental institution, Homer comes back with a man claiming to be Michael Jackson (who is actually voiced by Michael Jackson). There’s so much excitement about MJ’s arrival in Springfield, that Bart once again shafts Lisa on her birthday, which he has done every year. Bart overhears Lisa saying she’s going to disown him as a brother, and panics. He and Michael collaborate together to give Lisa her birthday gift: a song just for her.
Why The Tears? Awwww Bart is being so sweet! The lyrics to the song are easy to sing and the tune is so happy and jovial (warning: if you listen to it, it will be stuck in her head BIG TIME). Plus, given the untimely and recent passing of M.J. this episode is extra sentimental to watch.
4. Season 4, Episode 15 “I Love Lisa”
What’s Sad? On the surface, this is set up to be a pretty easy to watch Valentine’s Episode. NOPE! Everyone in little Lisa’s class is passing around Valentine’s cards (as one does in elementary school), when Lisa realizes that nobody bothered to make a card for Ralph. Out of pity, Lisa gives him the now infamous “I Choo Choo Choose You” card, which sparks a romantic interested in Ralph. He invites Lisa to join him to a taping of the Krusty The Klown show, despite Lisa telling Ralph she does not like him “like that”. Mid-show, Ralph declares (on television!!) that he loves Lisa and he intends to marry her. Oops. Lisa goes nuts and reveals the truth; that she doesn’t love him and she gave him the card because she felt sorry for him. Damn Lisa!! Lisa apologizes and makes it up to him by giving him a card that says “Let’s Bee Friends”.
Why The Tears? Lisa is ice cold in this episode, dude. But Ralph needs to learn “no” means “no”! The tears are more sweet than sad at the end of the episode, and the “Choo Choo” card has now become more famous than the episode, itself! Consider it a history lesson then.
Fox
