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Months removed from the end of his late-night TBS show Conan, Conan O’Brien’s legendary career in comedy is such that his fans enjoy being on a first name basis with him; “Did you see this Conan video?”

O'Brien's career traces back all the way to his reign as President of the Harvard Lampoon in the 80's and continues on to the present, with a number of projects in the works. And in that timeline, as many know, O’Brien enjoyed a brief run as a writer on The Simpsons, where he's credited with multiple classic episodes.

In 1991, The Simpsons showrunners Al Jean and Mike Reiss offered O’Brien a job as a writer after his departure from Saturday Night Live. The Simpsons premiered in 1989 and was already a hit, winning multiple Emmys. 

From today's perspective, adding Conan to the The Simpsons roster was seemingly like Kevin Durant joining the Golden State Warriors. While O'Brien's move wasn’t viewed that way at the time, it had a similar outcome: some of the best episodes of The Simpsons hit television screens during his seasons four and five stretch as a writer, before his departure to host Late Night in 1993. 

Conan O'Brien never had 39 on 15 of 24 shooting against his old team, The Oklahoma Thunder, however.

TBS, Team Coco

We're not even sure he and Andy beat these guys.

Anyway. Comparing O’Brien to other Simpsons writers is difficult, as he was only there for two seasons and is credited with writing three episodes, “New Kid on the Block,” “Marge vs. the Monorail” and “Homer Goes to College,” plus the wraparounds on “Treehouse of Horror IV. 

For context, Mike Reiss and Jon Vitti have written 25 each, and Jon Swartzwelder is credited with 59. But as someone who routinely fails to meet their work quota would say, quality over quantity.

And because Conan's career is so vast and accomplished, his time on The Simpsons has reached mythical status. Sometimes, he's even mentioned as the greatest writer in the show's history. How does he actually stack up? We can only take a look at the work and decide.

We'll evaluate each episode by the criteria of IMDB ratings, best quotes and of course, my own, obviously strongly-desired, authoritative and objective opinions.

The Simpsons “New Kid On The Block” (Season 4, Episode 8)

IMDB Rating: 8.2 (112th)

O’Brien’s first writing credit on The Simpsons comes in this episode, where we see a lovestruck Bart Simpson infatuated by his newly-moved-in neighbor, Laura. Laura is essentially Bart’s analog, an older girl who loves pranks the same way Bart does. 

Warning: Unclear if Conan wrote these jokes, but The Simpsons were not above sexism and homophobia in 1991.

Things turn sour for Bart when Laura informs him she’s taken a boyfriend, and that gets worse when that boyfriend turns out to be Bart's tormentor and likely reason for future therapy, Jimbo Jones. 

Meanwhile, Homer finds himself enamored with an all-you-can-eat seafood deal at The Frying Dutchman (An excellent name for a crispy seafood place, if I may say). Homer being Homer, he pushes the physical limits of what a human being can eat, consuming everything in sight (Including two plastic lobsters) and is forced to leave the restaurant when it closes. Homer takes his grievances to my personal favorite side character, Lionel Hutz, to sue the restaurant for not allowing him to eat all he physically can. 

“New Kid On The Block” Best Quotes

Hutz looking at Homer’s case: "Mr. Simpson, this is the most blatant case of fraudulent advertising since my case against The Never-Ending Story!"

Homer talking to Bart about girls: 

"Son, a woman is a lot like a... a refrigerator! They're about six feet tall, 300 pounds. They make ice, and... um... Oh, wait a minute! Actually, a woman is more like a beer. They smell good, they look good, you'd step over your own mother just to get one! But you can't stop at one, you wanna drink another woman.”

Homer talking to Laura’s mom: 

“Homer: There was something else...something I was supposed to tiptoe around.

Ruth Powers: My divorce.

Homer: That's it! Woo-hoo! I'm glad one of us remembered. That could've been embarrassing.”

New Kid On The Block” Opinion And Analysis

While the story’s A-plot of Bart trying to woo his older neighbor/babysitter, a classic family storyline, Homer’s plot is where this episode truly shines. Marge brings the new neighbors a welcome basket, and Homer’s contribution is a porno for “the man of the house,” a decision made without the knowledge that the couple had divorced before moving in.

The episode truly hits its stride in the courtroom, like when the defense calls in a band of men carrying full sacks to show how much shrimp Homer ate. They dump them and out slides 18,000 letters addressed to Santa Claus. 

Fox

The men are told: “You want the people of Springfield vs. Kris Kringle. They’re next door.” 

Brilliant!

Homer and the Sea Captain reach a settlement, which results in perhaps the finest moment of the episode: Homer will be put on display at the restaurant as “Bottomless Pete: Nature’s Cruelest Mistake,” where he gorges himself on seafood in a mutually beneficial arrangement.

Bart’s plot has its moments; He ultimately frames/dethrones Jimbo by getting Moe after him in response to a prank call, causing Jimbo to cower and cry, which leads Laura to break up with him, a funny moment that shows the degree of bad boy she seeks. 

A young boy in love with an older girl is an arc that we've seen before in other shows, explored most often through a babysitter. It's a tad trite and makes Homer the real standout in this episode, but nonetheless, “New Kid On the Block” is a very solid Conan O'Brien entry.

The Simpsons “Marge Vs. The Monorail” (Season 4, Episode 12)

IMDB Rating: 9.1 (8th)

Conan's highest-rated and best-known episode, “Marge vs. the Monorail” is a fixture in Simpsons lore. After slapping Mr. Burns with a $3 million fine for dumping nuclear waste in the river, the townspeople come together to decide how to use the windfall. 

Marge suggests using it to repair Main Street and Springfield quickly embraces her idea. That’s when the smooth-talking monorail salesman, Lyle Lanley (Phil Hartman!), steps in and convinces the town, through song and dance, that a monorail is the best way to spend the money.

With the town fully on board, Marge remains a skeptic, as does Lisa. In the meantime, though, Homer is drawn to the idea of being a monorail conductor and is halfheartedly named to conduct the maiden voyage after not-so-rigorous training. 

Marge and Lisa remain the only skeptics of the monorail and Lanley, believing it to be an unsafe waste of money and him to be a huckster. The town is fully on board, however, leaving them alone to investigate further. 

Marge discovers a notebook outlining Lanley’s plans and visits a desolate town where Lanley had previously built a monorail. There, a scientist named Sebastian Cobb confirms to Marge what she believed: Lanley is a fraud and the monorail is terribly constructed.

Lanley flees the town before the monorail begins running, and when it does, it quickly and not-surprisingly reaches out of control speeds. Homer eventually stops the train by anchoring it down to Lard Lad’s Donuts and saves the day, while Lanley is attacked by the people of North Haverbrook, a town he’d previously conned, after his plane makes an emergency landing there.

“Marge Vs. The Monorail” Best Quotes:

Marge telling Homer he can stop the monorail:

Marge: “Homer! There's someone here who says he can help you.”

Homer: “Batman?!”

Marge: "No, he's a scientist.

Homer: Batman's a scientist?!"

After the monorail loses control:

Homer: “Are we gonna die, son?”

Bart: "Yeah... but at least we'll take a lot of innocent people with us.”

Homer after stopping the monorail: 

“Donuts. Is there anything they can’t do?”

“Marge Vs. The Monorail” Authoritative And Objective Opinions/Analysis

There’s a reason this is considered an all-time great Simpsons episode. It’s O’Brien at the peak of his powers, taking such a bizarre concept (Who thinks of a monorail financially crushing a town?) and combining it with a bizarre movie (Really? The Music Man?). The Monorail song is as catchy as they come, and if you're familiar with the episode, it’s probably now stuck in your head.

Marge, especially early on in the show, is often used as just a skeptic of Homer’s nonsense, and in this episode it’s clear why she’s at her best when she acts on that skepticism. Her arc is bolstered even further by placing her, along with Lisa, as the lone skeptic against not just Homer, but the entire town of Springfield. Lisa is the smartest character in the family but can find herself in tough spots attempting to demonstrate that, so Marge taking the reins on exposing Lanley gives her an opportunity to shine but also economically solves the main issue of the episode without Lisa’s hiccups.

The character of Lyle Lanley is an incredible piece of work by O'Brien that is so perfectly brought to life by the stellar Phil Hartman. He barely makes any effort to conceal his true intentions and Hartman's slick delivery proves that the two were a perfect pairing. 

“Homer Goes to College” (Season 5, Episode 3)

IMDB Rating: 8.6 (46th)

Originally intended as the season five premier, Homer Simpson plunges into a world he is completely unqualified for: College. 

A surprise safety evaluation by the Nuclear Regulatory Commission places Homer in a van during a simulated nuclear meltdown, a test which he predictably fails miserably, causing an actual nuclear meltdown in a truck that didn’t even contain any nuclear energy.

The NRC informs Mr. Burns that Homer’s lack of nuclear training or college education makes him dangerously unqualified for his job, forcing him to attend college. Unsurprisingly, Homer needs the help of his boss after being rejected by every school he applied to, and is admitted into Springfield University.

Homer’s impression of college is derived entirely from comedies about college, and he expects it to consist entirely of partying and beating up nerds. Springfield University, though, is far more based in reality, and everyone actually works at being students. After causing a meltdown in his physics class, Homer is assigned tutoring by three nerdy students who he inadvertently gets expelled in an attempted prank.

Homer offers the nerds a house to live in, and they quickly overstay their welcome. Homer’s plan to get them back in? A reverse prank. Spoiler alert: It goes poorly. Homer fesses up to the pranks to the dean and the students get back in. 

One last challenge remains: Homer is woefully unprepared for his final exam, and after cramming, fails. The nerds give him one last favor by changing his grade in the computer, securing Homer both an A+ as well as employment.

“Homer Goes to College” Best Quotes:

Smithers and Burns fleeing in an escape pod after the nuclear meltdown Homer caused:

“Smithers: For the love of God, there are two seats!

Mr. Burns: I like to put my feet up.”

Homer dancing and singing while burning his high school diploma and the family room:

“I am so smart. I am so smart. I am so smart. S-M-R-T. I mean S-M-A-R-T.”

Homer telling Marge how he passed college:

“Let’s just say I had some help from a little box.”

“You changed your grade on the computer?”

“D’oh!”

“Homer Goes to College” Authoritative and Objective Opinions/Analysis

While this is not a rankings piece, I’ll admit, this is my favorite of Conan’s episodes. There are two things that make it particularly enjoyable: Homer’s fundamental misunderstanding of college and how absolutely out of his depth he is.

We’ve all seen the likes of Animal House and Old School, so the tropes the episode leans into are easily recognizable; the movie he watches, “School of Hard Knockers,” includes a “bra-bomb,” which blows the bras off every student on campus. We know what we're in for with Homer when Marge pulls up to drop him off and he screams “NERRRRRRD” at a student walking by. A personal favorite scene of mine is when he’s on his bed listening to music and replaces his bookshelf with cinder blocks and shelves.

Universal Pictures

Needs one of these posters, though.

Then there’s his complete ineptitude. Everyone is significantly smarter than him; A joke made by his professor goes directly over his head, but he nearly falls out of his chair laughing when the professor drops his notecards. When he blows up a particle accelerator, he casually tells the nuclear responders it’s in there and they respond with “Thanks, Homer!” The Simpson patriarch is at his best when he’s in over his head.

Like I said, this one takes the cake for me, even over “Marge vs. the Monorail.” Homer going to college is a blank slate that can go a million different directions, and the path Conan charts here is the correct one.

The Verdict:

To borrow a phrase from my friends who are a lot cooler than me, O’Brien cranked out some bangers in his time with The Simpsons. In 2003, “Marge vs. the Monorail” was named the fourth best episode of The Simpsons by Entertainment Weekly. Writing a top episode is already enough to put you in the conversation of the greats like Vitti and Swartzwelder. 

If we’re to include his contributions to “Treehouse of Horror IV,” it’s most helpful to look at who else wrote four episodes. That would put him with the company of Matt Groening, Dan McGrath, Brent Forrester, Steve Tompkins, Allen Glazier, Valentina L. Garza and Mirranda Thompson. All fine writers who contributed to terrific episodes, but none score above “Marge vs. the Monorail” in IMDB’s ratings. That episode stands among the best episodes written by the likes of Vitti and Swartzwelder, and to do it in only two seasons makes one wonder how many more top-tier episodes O’Brien would have written if he stuck around longer. 

While O’Brien is not in that bonafide A-tier of writers, he’s around that neighborhood, you know right down the street from Ned Flanders, who once coveted his own wife.

For more ComedyNerd, be sure to check out:

https://www.cracked.com/article_31220_how-joe-rogan-went-from-fairly-unknown-comic-to-podcastings-demi-god.html

https://www.cracked.com/article_31570_why-ventriloquists-are-here-to-stay-whether-we-like-it-or-not.html

https://www.cracked.com/article_31843_the-simpsons-will-probably-end-with-this-gag-showrunner-reveals.html

Top Image: Fox

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