‘The Simpsons’ Oral History of ‘Last Exit to Springfield,’ The Best Episode Ever

Showrunners Al Jean, Mike Reiss, writers Jay Kogen, Wallace Wolodarsky and director Mark Kirkland weigh in on the episode’s 25th anniversary

Twenty-five years ago, “Simpsons” writers Jay Kogen and Wallace Wolodarsky begged their bosses not to cut the core joke in “Last Exit to Springfield,” the best episode in the history of the show.

It’s a long, weird bit that goes thirty awkward seconds without a payoff. The words “dental plan” and “Lisa needs braces” bounce around Homer’s brain as he waits in a beer line, until he blurts out a realization that reveals to viewers, for the first time, how dumb he truly is.

“It went on for a page and a half! We gotta cut this. This doesn’t make any sense at all,” Mike Reiss, who was co-showrunner of “The Simpsons” at the time, remembers thinking. “And Jay and Wally said, you gotta do it. Trust us on this.”

The idea of the episode is simple — Homer Simpson becomes a union leader to fight for his dental plan — but it spawns endless jokes, movie and TV parodies, and even a folk song. Outlets from USA Today to The Ringer have named “Last Exit to Springfield” the best “Simpsons” episode ever, which it is.

But the writers told TheWrap that “Exit” — which premiered 25 years ago this Sunday, on March 11, 1993 — was just another episode to the frazzled, exhausted “Simpsons” team. The writers were so burned out that the next week’s episode was a clip show.

Here is the complete oral history of “Last Exit to Springfield.”

‘The Big Book of British Smiles’

Wallace Wolodarsky (co-writer): I hated my orthodontist. I hated him. He was horrible. He was mean, and he was never nice. That’s what brought around my psychoses before I got to take advantage of it.

Jay Kogen (co-writer): I remember Wally being instrumental on that dental scene. All the dental tools, “the gouger, the scraper,” those are Wally’s jokes as far as I remember. He also created the Big Book of British Smiles.

Big Book of British Smiles

Wolodarsky: I know, so ridiculous. It’s almost like if you’re a comedy writer, it’s almost like cheating.

Mark Kirkland (director): And then there was the hilarious step-by-step pathology, that this will give [Lisa] fangs if we don’t go through with braces, so another just really fun visual thing. I went to my dentist, and I asked him at the time, do you have tools named this, this and this? And he just laughed at me.

Al Jean (Season 4 co-showrunner): The dentist, we asked Clint Eastwood originally, and I don’t know what the exact wording was, but it was “hell no.” And we’ve never had him on the show. The second person we asked was Anthony Perkins, and he really wanted to do it, and then very sadly, something was wrong, we couldn’t get him to come into the studio, and then he passed away, which is really sad. He would’ve been fantastic. So we wound up with Hank [Azaria], who was great.


Wolodarsky: The story is very easy to understand. You lose your dental insurance, or Lisa will have horrible braces. Now you start to hang every last joke that you can on it. You never think about weighing heavy themes, though it does have one of my favorite themes, which is labor versus management. As a person who’s in multiple Hollywood unions, I’m very much a labor person. So that was fun to put the labor message out into the world. As it’s been the case for many years now, labor has been crushed every which way. It was fun to see labor as the hero.

Jean: I have to give credit to Mike Reiss, who suggested the idea for the episode that Homer becomes union leader. … We were conscious of being very even-handed at the time. There were many more moderate Republicans and there was a real sense, although I think many of the writers always leaned liberal, most of them, not all of them, that there was a sense that you wanted to respect both sides.

Mike Reiss (Season 4 co-showrunner): At the time, Al and I were running the show, and the bosses had sort of backed away. Jim Brooks and Matt Groening had let us do the show ourselves, so I think that fourth season just starts getting a little crazier, moves a little faster. We weren’t trying to please anyone above us, and we were just getting to do it the way we wanted to do it.

We skew pretty liberal, but we always say don’t get your opinions from “The Simpsons,” and we don’t want the show to be preachy. If we start advocating in one direction, we always want to show the other side of it. Al always used to say, “It’s not liberal, it’s nihilistic.”

Wolodarsky: There’s an unspoken word in the office that everything is up for grabs. You can make fun of everything. There was never a moment of, I don’t want to make fun of unions because I believe in unions. Because I do believe in unions. And unions can be corrupt and cynical organizations. We never limited ourselves in terms of who we were going to go after.

Lisa Needs Braces

‘Dental Plan… Lisa Needs Braces’

Kogen: I remember writing the joke where the dental plan is going to be taken away. Mr. Burns offers the beer instead of the dental plan. “Dental Plan, Dental Plan, Dental Plan,” and Homer still doesn’t get it. The voice repeats in his head in the traditional movie style where he hears it once and is supposed to go, “Oh my God!” But he doesn’t get it and hears it a thousand times and doesn’t understand it. I remember that being a funny joke to me, and I wrote it so many times I thought for sure Mike or Al would cut it down because it was so long.

Kogen: There’s a joke that Jon Vitti wrote that’s identical to the shaping of the scene itself. I always quote it because I think it’s really funny. Homer goes into the freezer and takes a box of Neapolitan ice cream out, with vanilla, strawberry and chocolate ice cream. “Mmmm chocolate,” he says, and then finds out all the chocolate has been scooped out. Then he takes another box of Neapolitan ice cream and says “mmm chocolate,” and it’s all scooped out, and he screams to Marge and says, “We need more Neapolitan ice cream!” So it’s the same thing. He’s so myopic. He loves chocolate ice cream. He could just ask for chocolate ice cream. But instead, he wastefully asks for Neapolitan ice cream because that’s the system he’s trapped in. That’s a joke from [Season 3]. There’s no difference to me between that joke and trying to become a union boss in our episode.

Jean: Homer works best when you take something that’s relatable, something that you or I might do, and you boil it down to its simplest atoms. He just thinks about it simply, but it’s stuff that everybody really thinks about. In the same season, there’s a joke where he eats a sub sandwich and got sick because he kept it in his fridge for several days. That was something I did. You go, that’s crazy, but it’s based on some reality of somebody.

Kirkland: Early in the show’s history, Homer wasn’t as dumb. He got progressively dumber in this time, and I remember Jay and Wally liking the really dumb Homer. Why not? If it gets us the laughter we need, why can’t he be that dumb? That one might’ve pushed the envelope of, oh my God, he’s this dumb? But it works.

Homer the Don

‘The Godfather’

Kirkland: I can’t even count how many references to other movies there were or TV shows: “Lucy in the Sky with Diamonds,” “The Godfather,” the “Get Smart” thing. From a social commentary, when the town blacked out and the town immediately started rioting, I think we had just come off the LA riots, and I think it was a social commentary on people doing that.

Jean: We assumed our viewers had a wide range of cultural references. It wasn’t like now where you could look anything up on Google. But it was also like “Bullwinkle,” where if you didn’t get it when you were 10, you would get it when you were 20, and it would add to your enjoyment of the show later.

… It was at the time when we were breaking the reality of the show just ever so slightly. We would do the “Yellow Submarine” parody. The big thing I remember about that was that we had to completely make it different from “Yellow Submarine.” I think we called it the Purple Submersible. You look at each character, and each character there’s a real clear legal distinction between the Beatle it was representing. That’s the sort of thing we were putting more of, cutaway jokes, than had been in the show in series previous, and I think they work really well in that one.

Kirkland: We had specific directions to make them like The Beatles but they’re all different. They’re all mixed up and different. I also remember drawing, it said in the script, a “campy engraved Queen Victoria.” It says that. And as a kid, my parents are Canadian. And in our house, we have this antique portrait of Queen Victoria in my house, so I knew exactly what to do when it came to doing that.

Wolodarsky: We really just enjoyed reprocessing all of the stuff we had been ingesting for so many years as pop culture lovers. It doesn’t follow any program. “Remember that feeling when you took gas and you felt high?” That leads you to psychedelic imagery and that leads you to, “Yellow Submarine” would be perfect for this. The same thing for “The Godfather.” We knew “The Godfather” backwards and forwards. So it was our way to insert our love for these other movies.

Jean: We had done a lot of “Godfather” parodies, but the Little Italy scene I think wasn’t the most obvious, and I love Homer being that Don.

Kirkland: When I did storyboarding myself for Homer the Don, I watched “Godfather Part II.” He’s in the white suit walking around picking up apples off the apple cart, bouncing them in his hand the way Homer is doing it with the donut. But I remember for sure popping in the VHS and copying the staging. I always loved “Godfather Part II,” so for me, this is really cool for Homer behaving like this. Of course it’s all about donuts.

Reiss: I’m guessing that is what people really like about it, dense, irreverent. Did I catch this, did I catch this? It’s all on Wikipedia now though. I remember looking at the moment of Lisa looking at herself in the mirror and smashing the mirror, and I remember at the time it was a very timely joke because it was Tim Burton’s “Batman,” but now people wouldn’t recognize that reference.

Kirkland: It was so imaginative. All of our “Simpsons” are imaginative, but this one is more surreal somehow. Maybe it’s just more of it, more of the dreams and kooky satire and the “Get Smart” bit…  They finally end up in a room with the main computer and it’s got a screen door with a stray dog. And Burns, like the villain he is, kicks a dog! The gags flew at you.

Reiss: Our stamp on the show was that we did more and more of those things. Finally out of desperation, I know we could tell a story so fast that we had to plug it with little holes and other freestanding bits. Like, a few years later we did a Mary Poppins episode, and that episode is almost all padding and cutaways. It’s not only padded in that it’s musical for musical numbers, but half the episodes it’s people watching other things on TV. It just always worked on the show, no matter how much we revved it up, it still always worked, and you could still get the references. And when “Family Guy” came along, they went even much further in terms of the cutaways being more abundant and more far flung and more off topic, and people could still enjoy it.

Now Do Classical Gas

‘Now Do Classical Gas!’

Kogen: I think I was listening to “The Times They Are A-Changin’,” and I tried to write something in the theme of that. And then in the rewrite, it got morphed into the song it is now through Mike and Al. The song I originally wrote is about half there. The song Wally and I wrote is about half to two-thirds there, but it got changed around to not be exactly like “The Times They Are a Changin’.” I usually think “The Simpsons” does a good job of parodying songs, but this became its own song.

Kirkland: Paul Wee, he’s one of our great animators. And he said it always bugs me when I see characters playing instruments and I can tell. He said it may not be perfect, but it passes, and he made an attempt to hit the right chords. That is the kind of detail that can be put into these things. And he’s the same guy by the way who did the “Batman” thing with Lisa and the mirror.

Jean: It was the year 2000, and I met Mason Williams, the composer of “Classical Gas,” and he mentioned how happy he was that we used it in the show. I had loved the Smothers Brothers show that he was on, and that meant a lot to me.

Reiss: My only other big contribution I remember to this episode, I said let’s end it like “The Grinch,” where Mr. Burns has sort of a change of heart. That’s my other big contributions to “The Simpsons:” “Let’s steal this great thing from somewhere else and do it here.”

Kirkland: That was animated by my assistant director, Susie Dietter. She was a fanatic. She loooved “How The Grinch Stole Christmas.” She asked me, can I do that section, and I said sure. She put a lot of love into the posing to get it just right. At the time we were working at Film Roman, and Phil Roman had worked on “The Grinch.” He was down in our office area giving a tour when Susie was working on that, and she got to show him, and he just loved seeing that. For us that was special in a way. Here’s a guy who actually worked on that, and he enjoyed watching us doing it again.

Simpsons Batman Parody

‘We Never Revisited It’

Jean: To show you how things surprise you, “20/20” came and filmed the writer’s room once, and once only, because we never let them back in. It was working on that episode. We were working late, we were unshaven, and they kept filming us just not thinking of ideas. It was really depressing. It made us look like completely uncreative idiots. That was when we were working on the montage for that episode, and I just go, it’s funny that this thing that was so embarrassing when we were working on it is now regarded as one of the best things we ever did.

Reiss: Just to put it in perspective, even though the episode was really funny and to show how it was not a standout to us, we never revisited it. We never brought back that dentist. We never saw Homer’s union again. There are other shows like the monorail where we go back. But this episode, I don’t remember “The Simpsons” ever talking about it again or ever bringing back any aspect of it again. It’s all flattering when fans told us this is a really good one instead of us being proud of it ourselves.

Jean: I did look up, the first time I saw a recorded example of people saying that the show lost it’s way was the premiere of Season 2, “Bart Gets an F.” They were saying it’s just not the same as it was in the first year. I’ve been seeing it for 28 years. I don’t know when it ever came true if it did, but I’ve seen that consistent criticism for that long. The basic fear we’d had in Season 4 is that maybe it was getting too crazy. And then, as they would say, a few years later I would see “Last Exit to Springfield” as Number One on the list of best episodes of all time, I would be a little surprised.

Kirkland: One day I’d have three of my shows on the top 10, and the next time there would be some list, I’d have none. Whoever is writing these lists, they have a new favorite all the time. But it’s probably the one I’ve done that’s the highest on the list in my career. It’s probably the one that’s most consistently on the Top 10.

Kogen: It seems picked kind of randomly. It’s not even my favorite episode that we wrote, let alone everyone’s favorite in an entire 30-year series. That may be a value that happens over time, and other things will take its place. I don’t know if there’s truly a consensus, because who judges that? They’re just loud enough to say this is better than that.

Wolodarsky: To Jim’s credit, because he was looking over everything, the story mattered, and the emotional content of the story mattered. Speaking for myself as a young writer, it was something I didn’t care about it, because I was given these opportunities to write these funny jokes, like I got so excited about that. And Sam for sure taught us this lesson: what’s the emotional content? If you go back even further than that, Matt had lots of heartfelt, childhood sentiments that found their way into the show. By that point we all understood that. Why it’s considered the best is totally beyond me. I have no idea. I’ve heard that before from people, and it seems like a really good episode from a really fun year, but is it the best? I don’t know about that.

The Simpsons Last Exit to Springfield

Best. Episode. Ever!

Reiss: About 15 seasons into the show, I saw USA Today had ranked it as the best of the first 300 episodes of “The Simpsons.” And I called Jay Kogen and said, “They picked your episode “Last Exit to Springfield” as the best episode ever. And he said, “It wasn’t even the best one we wrote that month!”

Kogen: I would always be proud because my name was on it and Wally’s name was on it. And also be a little confused because so many great episodes came from that period of time on “The Simpsons.” Why this one? Why is this one better than the others? Maybe I’m too close to it.

Jean: At the time I thought it was a very funny episode like the other ones we were doing, and I didn’t think it stood out as much as something like the monorail episode or the “Streetcar” episode.

Wolodarsky: It was very much in the pipeline of the show. The funny thing about the show is, we would take things that had happened to us, braces for example, and the whole experience of going to the orthodontist, and graft it on to a bigger story about the union. That was always one of the fun things we learned from Sam Simon. He had this great habit of taking two stories, or rather letting one story that didn’t seem connected start a second or third act story.

Reiss: It was part of an assembly line. We never dwelled on it; get that one done and on to the next one. I don’t remember it being a stand out at all during production or even after it went on the air. So for people to single it out even a few years later or talking about it 25 years later, it’s always a surprise to me.