The Simpsons is the funniest show of all time, but it’s also one of the most tragic. Think about it: Homer is an overweight drunk who hates his job; Marge gave up her dreams for her husband; Bart is “underachiever and proud of it,” meaning he’s already stopped trying, even in elementary school; Lisa is a clinically depressed eight-year-old; and Maggie is only a toddler and she’s already shot someone. And that’s not to mention the lives of Milhouse, Hans Moleman, Martin Prince, Nelson Muntz, and so on.

But there’s a difference between tragic, which can often be funny, and depressing. Allow me to present to you eight episodes of The Simpsons that made me shed a tear or two, often out of sadness and occasionally out of joy.

#8. ‘Round Springfield

Everything we know about Bleeding Gums Murphy is from this episode, where he tells Lisa his life story: how he received a “saxophone” from Blind Willie Witherspoon, how he got his big break on Steve Allen’s Tonight Show, and how he became broke ($1,500 a day Fabergé egg addiction). We also learn that he hasn’t worked since a 1986 appearance on The Cosby Show, meaning Murphy’s been unemployed for nearly a decade. Even Lisa comments, “A lifetime of jazz leaves you sad and lonely.” He’s now in the hospital for unknown reasons, and a short time after giving his saxophone (note: not an umbrella) to Lisa, he passes away. The look Lisa has on her face when the nurse tells her isn’t even the episode’s most depressing moment, though – it’s when only Lisa, Marge and Homer (and the hot dog man) attend his funeral, where Reverend Lovejoy calls him “Blood and Guts Murphy.” Even Grimey had more attendees.

#7. That 90’s Show

Whether you want to admit it or not, there have actually been a few great later-era Simpsons episodes, including “My Fair Laddy,” “Eternal Moonshine of the Simpson Mind,” and “That 90’s Show,” even though it makes no logistical sense. It’s some time in the early 1990s, and Marge is a student at Springfield University and Homer is working at a laser-tag warehouse, paying for Marge’s tuition. She begins falling for a professor, though, and Homer gets jealous – so much so that he reforms his R&B band (don’t ask) into a grunge (that’s Guitar Rock Utilizing Nihilist Grunge Energy) group called Sadgasm. One of the band’s songs that gets played on MTV is called “Margerine,” and although it sounds a bit like Bush’s “Glycerine,” Gavin Rossdale only wishes he could writing something as good as: “Spread yellow gunk on my pancake heart/Country churned girl in my grocery cart/I paid for her dreams, she taught me to cry/Like watery knives, like rain from my eyes.” And with that, we have the saddest grunge ever song written (sorry, “Down in a Hole”).

#6. Bart Sells His Soul

I can think of a lot of things cooler than expanding sponge dinosaurs to sell your soul for (namely, Alf Pogs), mainly because I don’t think they’ll actually become life-size and eat my sister. That is why I’m not Bart, god bless him. But that’s just funny. The real heartstring tugging comes from a dream Bart has, where the kids of Springfield team up with their souls to row a boat to an island. With the way it’s animated, all green sky and pink grass it’s both creepy and pitiful. Creepy because of Sherri and Terri rhyming, “Bart, it’s time to end this dream/And don’t forget the standard scream,” and pitiful because Bart’s 10 years old and he’s already questioning his own existence. His mom basically calls him a monster, too. The saddest scene is when you see Bart trying to row, but because he’s without a partner, he’s just going around in circles. In his PJs, to boot.

#5. Home Sweet Homediddly-Dum-Doodily

After Child Protective Services come and takes Bart, Lisa, and Maggie away from Homer and Marge, for being “negligent monsters,” and places them in the foster case of the Flanders, the kids do whatever they can to get in touch with their parents, including making a phony newspaper with Rod and Todd. The Flanders Press has two headlines: “Todd Smells,” which we already knew, and “Simpson Kids Miss Mom & Dad.” Considering I’m someone who both cried when doing things by himself and made fake newspapers to amuse myself, this one got to me. On the plus side, I do know how to take care of a houseplant.

#4. And Maggie Makes Three

This selection is more tears of joy, but tears nonetheless. At the beginning of this flashback episode, Homer quits his job at the power plant, in order to achieve his life-long dream: working as a pin monkey at the Bowl-O-Rama. Homer’s finally happy doing what he’s always wanted to do, until Maude Flanders “tells” him that Marge is pregnant again. Homer knows that his job won’t pay enough for another mouth to feed (“We’re doomed, doomed I tells ya!”), so he resigns from his position, receiving a non-acid rain resistant jacket as a parting gift, and goes back to the power planet, literally begging Mr. Burns on his knees. Burns accepts his return on one condition: Homer must have a plaque in his workstation that says, “Don’t Forget: You’re Here Forever.” As Marge goes into labor, Homer’s still angry about this development, holding the unborn child accountable – until Maggie grabs Homer’s thumb with her tiny hand for the first time. The episode ends with us seeing what gets Homer out of the bed and into work every day: pictures of Maggie covering Mr. Burns’ plaque so all that’s visible is “Do It for Her.”

#3. “Marge Be Not Proud”

For years, my mom and I have argued whether Marge, if only for a second, stopped loving Bart after he steals a copy of Bonestorm and lies about it. As a mother, she, of course, says, “No good parent would ever stop loving their child, even for a single moment.” I, on the other hand, the son, say, “No, Mom, you idiot!” Either way, it’s heartbreaking the way Marge sadly mutters “oh, Bart” when footage of him stealing the video game is played in the Try-N-Save. I can’t quite comprehend what Marge must be feeling at that moment (most 23-year-old males without children can’t), but that doesn’t mean it didn’t resonant. I’ve done a lot of shitty things to my mom in my life, but I’ve never truly disappointed her. The thought of doing so makes me reach for the proverbial box of tissues.

#2. “Mother Simpson”

Homer’s mom, Mona, returns to him for the first time 27 years, after she leaves him in the middle of the night when he was a child, and Homer, ever the gullible momma’s boy, believes she’s there to stay. But after an ABBA-playing FBI raid, she’s on the run again. But at least this time, Homer can say goodbye to his mom. The last scene of the show has Homer sitting on the hood of his car, looking up at the stars, as one of Alf Clausen’s saddest scores plays. Even more sad is how many times the writers went back to Mona as a character; after this episode, she’s appeared twice, in seasons 15 and 19, where she actually passed away. Yet, somehow, the sight of Homer resigned to the fact that he’ll never see his mother is more depressing than when he’ll actually never see her again.

#1. “Lisa’s Substitute”

As a child, especially a misunderstood one, you grab on to whatever attention you can get. I was too oblivious (read: dumb) as a youngster to really think about the lessons I was getting from my teachers, but for Lisa, with a father Homer like, that’s all she’s got; she needs to someone to intellectually look up to. Her second grade teacher Miss Hoover ain’t it, though, which is why she immediately falls for Mr. Bergstrom, the substitute for Lisa’s class while Miss Hoover is out sick. If Lisa were a decade older, she would probably have tried to seduce him (where have I heard that before?), but as a relatively innocent eight-year-old, she just wants to impress and know him.

Think about all the teachers you’ve had in your life: how many of them have actually had a life changing effect on you, let alone a substitute? Lisa finally found one, who taught her life is worth living – and then he has to leave, off to another teaching gig. Before leaving, though, he hands her a note with the simplest message of all: “You are Lisa Simpson.” Like Homer with his pictures of Maggie, this is what Lisa needs to keep going, a reminder of what makes her so special: herself.

Josh Kurp thinks the five greatest shows of all-time are The Simpsons, Arrested Development, Buffy the Vampire Slayer, Six Feet Under and The Sopranos.

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