COVID-19 has caused many creatives to use their time in unexpected ways. For Gayest Episode Ever podcast cohost Drew Mackie, rolling into the umpteenth month of quarantine sparked unlikely inspiration. While doing research for a deep-dive into The Simpsons episode “Three Gays of the Condo,” Mackie tried to figure out who the show first implied was gay via some sort of queer Simpsons supercut. “I was like, shit, this doesn’t exist anywhere,” he tells NewNowNext. “I have to do it.”

The result, “Smithers & Beyond: Every LGBT Joke on The Simpsons Ever,” is a two hour-long journey through every gay joke, character, plot, and inference in the show’s first 32 seasons. And it comes with some unexpected twists and turns concerning LGBTQ representation.

To parse through three decades of gay and trans jokes — ranging from the unexpectedly affirming to the downright transphobic — I spoke to a few queer Simpsons scholars to take a measure of just how far we’ve come since viewers were first introduced to the residents of Springfield, USA.

What did you first notice about the changing nature of the jokes through the years?

Drew Mackie (Cohost of Gayest Episode Ever; creator of "Smithers & Beyond: Every LGBT Joke on The Simpsons Ever"): It was interesting seeing the point at which they decided that Smithers is gay. At first, the joke is that Smithers is a weirdo who's sexually attracted to Mr Burns, and he's not gay. And then they start to bring other elements of gay stereotypes in his character, and he evolves from being like Burns-sexual to, not a healthy gay person, but a gay person. That was a weird thing to internalize, because I would have been about 7 years old when I started watching that. The idea of Smithers being a weirdo was probably the first thing I picked up on.

Henry Gilbert (Cohost of Talking Simpsons): What struck me at first was seeing a timeline of American perceptions towards queer issues deepen and change, as well as seeing the creators of the show itself grow in their understanding of gay issues. I noticed that simply the idea of a gay man like Smithers appearing on screen and existing was a joke, and by now, the idea that his character could be in the closet seems ludicrous.

Kat Bailey (Journalist): A lot of jokes in the ‘90s are the expected “gay panic” jokes, specifically the joke of constantly coding Homer as gay in a goofy way — having people be worried about being perceived as gay, having Bart be abused or bullied because people perceive him to be gay, along with Martin Prince and Millhouse. “Homer’s Phobia” (with special guest John Waters) is this watershed episode where a gay person is allowed to be human for the first time. But even in that episode, there’s still a bit of gay panic because Homer is worried about Bart being gay.

Why are some characters allowed to "come out" (Patty, Smithers) while others remain in the closet?

Jonah Flynn (Cofounder of “No Homers Club”): Some of the gay-coded characters are just peripheral characters who appear for maybe 5-10 seconds at a time and just have never had the spotlight to develop beyond that (for example, the choreographer in “Lisa the Beauty Queen” or the original actor who played Fallout Boy in “Three Men and a Comic Book”). Homer’s assistant Karl in Season 2’s “Simpson and Delilah” is voiced by Harvey Fierstein and kisses Homer, but is never explicitly stated to be gay. The kiss is not played as a joke either, which is great. This episode was made in 1990, and I would bet the reasons he’s not out in the episode have more to do with the times. In 1990, professional environments weren’t as accepting and open towards gay people. Even today, so many queer people still stay closeted at work. But there was certainly more shame and secrecy around it in 1990. … Also, Lisa’s music teacher, Mr. Largo, who was coded as gay for about 20 years, gradually became one of the show’s openly gay characters. He didn’t have a big coming-out moment, but in the past few years he’s seen with other gay characters, openly dates men, and is even shown in a long-term imperfect relationship with another man. It’s nice to see a peripheral gay character fleshed out and treated like a real person, rather than an exaggerated gay stereotype or punchline.

Gilbert: I think in part, it's the general comedy writer mindset when it comes to how jokes are executed in the world of The Simpsons. Going against expectations is a huge part of the spirit of Simpsons comedy, as well as having fun with the ambiguity of a given situation. From that mindset, having a character just openly address their identity goes against the grain to a degree, so I imagine that has something to do with it.

Mackie: Smithers does get a coming-out episode, but it’s fairly recent (“The Burns Cage”). It’s the one where he tells Mr. Burns that he’s gay. Everyone else already knows by then. I think it’s a writing problem because at some point, in order to make those jokes about Smithers, you have to imply that everyone knows he's gay. It’s just like an open secret. So much of the gay humor was given to him that it didn’t seem necessary to “out” him, whereas Patty had been much more “closeted.”

Was there ever an openly gay writer in the writers’ room?

Bailey: The Simpsons writers’ room has always been a lot of Harvard grads and very frat-oriented. At the very beginning of the show, there was a producer who explicitly said he didn’t want women writing on it. There was a woman who helped write one of The Simpsons’ Christmas episodes, I believe. There’s definitely a fraught history with that, where it’s just straight cis dudes of a certain age for a long time. And you can see that in the humor because so many of the jokes are callbacks to growing up in the ‘60s.

Flynn: To my knowledge, there has never been an out gay writer on the show’s staff at any point in the show’s history, at least not on the permanent writing staff. I think this is definitely one of the reasons the show’s queer characters have often defaulted to one-note stereotypical representations, and why it took so long for the show to feature any out gay characters. When you look at the best and most multi-dimensional gay characters on the show, most of them were voiced by actual gay people who really helped inform the character. Some examples would be John Waters as John (Season 8’s “Homer’s Phobia”), Scott Thompson as Grady (a recurring character since Season 14) or Patty’s new girlfriend Evelyn played by Fortune Feimster (Season 31’s “Livin’ La Pura Vida.”)

Mackie: The writer of “The Burns Cage” [Rob LaZebnik] wrote it for his son, who came out in high school. Working through that with his son got him wanting to write a coming-out story for Smithers. There is a writer who transitioned after the fact (Jennifer Ventimilia, who came out after writing for the show). If you look at current Simpsons episodes, there are several women writers as opposed to, like, one. There are two jokes that actually use the word “transgender.” I don't think they mentioned the word “bisexual” once on that show, which is rare because it's been on for 32 years. You’d think someone would say bisexual or bi, but they don't.

I've noticed that many of the jokes are concerned with transness rather than gayness and often the two blur together.

Flynn: In the first decade of the show, Bart is shown wearing women’s wigs, high heels, cheerleader outfits, and Marge’s dress. I never really read those moments as implications that Bart was gay. I saw them as acts of rebellion and confidence. I also don’t think we were intended to mock him for it, but rather laugh because of how surprisingly comfortable Bart is in his own skin. I think it’s a different story when Martin dresses in drag, though. He wears a skirt in “Treehouse of Horror III” and accidentally calls himself the “queen of summertime” in “Bart of Darkness” before quickly correcting himself. I think these examples differ from Bart in a negative way, because other characters in the scene react negatively towards him (Nelson even punches him), which reinforces to the audience that Martin should be mocked for behaving this way, whereas Bart is celebrated.

Gilbert: That continued conflation of transness with cis homosexual men, in particular, was pretty shocking to me when watching Drew's compilation. I had forgotten so many of those jokes. Sadly, I think that for the straight guy writing staff who are mostly left-of-center, they just saw gay and trans situations as interchangeable, and the same goes for conflating drag and transness. Most media did that back then — even myself as a gay man, I didn't know any openly trans people until I moved to the Bay Area in 2006, and I thank those friends for teaching me so much. That ignorance probably led to Simpsons audiences in the past also conflating the two groups as the same. ... Late in the video, I was pleasantly surprised to finally hear Marge say the word "transgender," which shows that at least some learning eventually happened with the producers.

Bailey: I think in the ‘90s, there was a certain cultural awareness of transness, but it was always treated as something that like “weird” people do. Like there’s a joke where Homer talks about Frank, who slept with his parents, I think, and then became Francine at a certain point — that was the type of joke you’d get. Or there was a moment where Otto asks if Patty is trans. That’s a way to take away femininity, and of course trans masculine people don’t exist at all in this world. But there are some really vicious jokes about trans people especially getting into the 2000s as visibility spreads. There’s a whole episode that’s basically just Queer Eye for the Straight Guy, which I remember being a watershed moment around 2004, where Homer gets a makeover. You can see the change just from the John Waters episode to the Queer Eye episode because it’s like, they’re cool and fashionable now. That’s how we were starting to perceive of gay men in 2004. And of course there’s Patty’s arc where she comes out as gay and gets married during that season. It was an important episode as well: They basically retconned her from being asexual to being a queer woman, which, I don’t know how I feel about that. There’s also a running gag about Homer loving women’s underwear.

Gilbert: The Simpsons always references popular films and TV shows throughout the years, so it's bound to touch on popular queer media like Brokeback Mountain, Thelma & Louise, or RuPaul's Drag Race. But by removing a lot of the explicit gayness from those moments, it both helps them get controversial topics past the Fox Network censors, and also it can surprise the audience with adult movie references you might not be used to seeing in a cartoon. For The Crying Game in particular, I think it got parodied a lot by The Simpsons and other comedies of the early '90s as a way to sneak in jokes they normally couldn't, mostly for the worse. The many awful "yuck, she's really a man" jokes of that era were bad then and look even worse now.

The teen boys in the show are obviously stuck in the ‘90s, and thus find the word "gay" as an insult eternally hilarious. Do you think there will be a point in time when viewers will look at The Simpsons and think, "Wow, those little kids were so homophobic for no reason!"

Flynn: I hope so, because that will be an indication that society has become a lot less homophobic, and kids aren’t using “gay” as an insult anymore. I already find myself occasionally caught off-guard by some of the outdated gay jokes I see in reruns of The Simpsons, South Park, Seinfeld, and other shows I watched growing up. Goes to show how far we’ve come in the last 20 years.

Gilbert: In the ‘96 episode "Lisa's Date With Density," when Nelson is caught on a date with Lisa, his bullying friends say "that is soooo gay" as an insult. It's a comical moment of boys being so ignorantly homophobic that they call a heterosexual kiss "gay," but it is a bit more shocking these days to hear that term used as a pejorative. I was a closeted teen when that episode came out, and using "gay" in that way was both very hurtful to me and so many others, though at the time I laughed at the joke and understood that to accurately portray mean boys in 1996. In moments like that one, I definitely think The Simpsons is attacking the bullies for their ridiculous level of homophobia, and the show doesn't think they should use "gay" to mean something negative. In the context of that scene, I think it's accurate for the bullies to use the term, but I hope that eventually those moments make people say, "Wow, I can't believe homophobia was so normalized back then!"