Tyler Vendetti
March 09, 2015 12:34 pm

On Sunday, Sam Simon, one of the original creators of The Simpsons, passed away at age 59, after a long battle with cancer. Simon, who started drawing cartoons as a student at Stanford, joined TV’s longest running series at the start and helped develop the landscape of Springfield as we know it today.

When the series launched, it was Simon who chose the writers, ran the writer’s room and created from scratch characters like Chief Wiggam, Mr. Burns and Dr. Hibbert. And that was just the beginning of his contributions to the series.

“He insisted that the show be created using some conventional sitcom techniques like having writers work collectively,” writes The New York Times‘ William Yardley. “He had the voice actors read their parts as an ensemble, with the goal of giving the show more lifelike rhythm and timing. And he hired many of the show’s first writers, a number of whom gave him credit for informing its multilayered sensibility, one that skewers pieties with anarchic humor and sometimes vulgarity while celebrating family and community.”

Although Simon left the series after the fourth season, he retained his Executive Producer credit. And considering his role in shaping some of TV’s most brilliantly original characters, that only makes sense. With his work on The Simpsons, Simon amassed a fortune, much of which he donated to charitable organizations. Then, in 2013, he officially announced that nearly all of his royalties from the series would go to charities through his organization, The Sam Simon Foundation, after he passed.

Although the Simpsons money provided Simon the chance to flourish as a philanthropist and serve organizations close to his heart (from animal shelters to feeding the homeless), he recalled, in a recent interview with Vanity Fair, how working series provided some of his happiest moments. “The No. 1 pleasure by far was how great everybody was,” he said. “It just doesn’t happen that everyone in the room is so great. So original.”

He added: “I was not confident that the show would be a hit, but I always had the confidence that we could do 13 great episodes that we could always be proud of.” Make that well over 500 episodes and counting. It’s truly hard to pinpoint the greatest Simpsons episodes ever, because there just are so, so many great ones. But we did select a handful that left a serious imprint on our TV brains. So in honor of Simon’s timeless work, here are some of our favorite eps of all time.

1) “The Itchy & Scratchy & Poochie Show”

Anyone who thought Tom & Jerry taught some questionable morals never watched Itchy & Scratchy. The “cat and mouse” cartoon that Bart and Lisa loved was always entertaining, but in one of those disturbingly funny, “I-would-never-let-my-kids-watch-this” kind of way. In this season 8 episode, the duo encounter a new character, Poochie the Dog, voiced by Homer, who has volunteered for the part in an effort to save the show from cancellation. Though they kill off Poochie in the second episode (his non-violent persona didn’t appeal to their young, gore-obsessed audience), the whole endeavor provides an interesting commentary on the TV industry.

2) “Last Exit to Springfield”

I should probably preface this bullet by pointing out that I have never actually seen this episode, so I run the risk of dying emotionally unfulfilled at any moment. However, every Simpsons fan I’ve talked to has cited this episode as one of the best, so I feel like not including it would be some sort of crime. “Last Exit to Springfield” takes a serious subject (work unions) and satirizes it through sly film references and puns. Many Simpsons scholars have named it the funniest episode of all time, which makes me even more sad that I have not watched it.

3) “Homer3″

Good? Or traumatizing? That’s the question I constantly ask myself about “Homer3,” the third part of the “Treehouse of Horror” episode. In the segment, the lovable, dim-witted Homer stumbles into the “real-world” and faces the struggles of three-dimensionality. That is, until he finds an erotic-themed pastry shop and forgets that he suddenly transformed into a live-action blob. Sooner or later, he’ll realize reality is not all that, just like the rest of us. (Cynicism!)

4) “Mr. Plow”

Out of all the TV props that I’ve ever wanted to steal, Homer’s Mr. Plow jacket pretty much takes the cake. Not only does the episode end on a weirdly inspirational note (Homer saves his friend-turned-business-enemy from an avalanche and the two set aside their differences for the sake of their friendship), but it also birthed the Mr. Plow jingle that will go down in history as the best jingle of all time.

5) “Holidays of Future Passed”

One slightly creepy characteristic of cartoons is their timelessness. Literally. The Simpsons has been playing since 1989 and Bart, Lisa, and Maggie are all still the same age. (And, more significantly, Marge has been raising 3 children for 25 years and has made no progress.) “Holidays of Future Passed” gives us a glimpse into what the show might look like if they stuck to an accurate aging timeline. Lisa marries Nelson. Bart flunks out of college. Maggie goes through an experimental music phase that leads her to superstardom. It’s everything that you’d expect to happen, seen through a series of Christmas photos and memories.

6) “Pygmoelian”

Looks aren’t everything, a lesson that Moe the bartender had to learn the hard way during this eleventh season episode. After getting rejected from the Duff Beer yearly calendar for being ugly, Moe invests in plastic surgery to make himself beautiful. Eventually, he’s hit in the face with a billboard, which botches his new look by turning him back to normal. It’s a classic take on the whole “it’s not what’s on the outside that counts, but what’s on the inside” plot line, but with a Simpsons twist (which is the best kind, next to a soft serve twist).

7) “HOMR”

What happens when doctors decide to remove a crayon lodged in Homer’s brain? Well, naturally, he turns into a super genius. Aside from disproving the existence of God to Ned Flanders (which is arguably one of the funniest Simpsons scenes ever), Homer also learns one of life’s greatest truths: that ignorance is bliss. Or, in his case, that having a crayon stuffed up your nose is better than having a high IQ.

Featured images Simpsons.Wikia.com.