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The Simpsons’ gayest-ever episodes and moments: A timeline

Stupid, sexy Flanders!

By Will Stroude

Words: Attitude; Images: 20th Century Fox

As The Simpsons’ Waylon Smithers makes history as the first Springfield resident to appear on the cover of Attitude, we’re taking a look back at some of the legendary animated series’ gayest episodes.

From Mr Smithers’ early unrequited love for Mr Burns to groundbreaking coming outs, here’s a timeline of some of The Simpsons most memorable LGBTQ moments…

Homer’s same-sex kiss: ‘Simpson and Delilah’ season 2, episode 15 (1990)

Homer hires an assistant named Karl, voiced by out gay actor Harvey Fierstein. While Karl’s homosexuality isn’t directly acknlowledged, he kisses Homer during a pep talk, deaclaring “My mother taught me never to kiss a fool” before slapping Homer’s buttocks.

Smithers’ Mr Burns fantasy: ‘Marge Gets a Job’ season 4, episode 7 (1992)

In this unforgettable fantasy sequence, a moonlit Burns flies in through Smithers’ bedroom window; the placement of the latter’s knee raised some eyebrows at the time.

Smithers’ gay retreat: ‘Homer the Smithers’ – season 7, episode 17 (1996)

When Smithers takes a long-delayed vacation, he’s seen jet-skiing with a human tree of hunks worthy of Kylie Minogue’s ‘All The Lovers’ video.

Steelworker circuit party: ‘Homer’s Phobia’, season 8, episode 15 (1997)

Fearing Bart is gay, a homophobic Homer takes him to a Tom of Finland-esque steel mill – where, it emerges, all the staff are gay, and gyrate to 90s hip house at break time.

Smithers kisses Mr Burns: ‘Lisa the Skeptic’ – season 9, episode 9 (1997)

Smithers has been trying to declare his feelings for a blissfully unaware Burns for decades. Most directly by kissing him upon mistaking a publicity stunt for a mall for the apocalypse.

Inside Smithers’ home: ‘Trouble with Trillions’ – season 9, episode 20 (1998)

An intimate glimpse of Smithers at home ironing his socks and singing ‘Everything’s Coming Up Roses’ from the musical Gypsy, Malibu Stacy dolls proudly on display.

“Stupid, sexy Flanders!”: ‘Little Big Mom’, season 11, episode 10 (2000)

“Feels like I’m wearing… nothing at all!” marvels a ski suit-clad Ned Flanders while shaking his rump — much to Homer’s libidinous confusion.

Homer’s gay roommates: ‘Three Gays of the Condo’ season 14, episode 17 (2003)

Homer’s allyship rating improves when he moves in with a gay couple. But when one of them kisses Homer, the world’s straightest male jumps out of the window.

Smithers’ weekend hobbies – ‘Three Gays of the Condo’ – season 14, episode 17 (2003)

How does Smithers spend his Saturdays? By rollerblading around Springfield’s gay village (“manly yet scented,” according to Homer) in teeny, tiny shorts.

Patty comes out: ‘There’s Something About Marrying’ season 16, episode 10 (2005)

The Simpsons made global headlines 17 years ago upon announcing a character was officially coming out of the closet. Smithers was the bookies’ fave, but it was in fact Marge’s sister Patty.

The Simpsons do drag in RuPaul guest episode: ‘Werking Mom’, season 30, episode 7 (2018)

Homer, Sideshow Mel and Smithers all get drag makeovers in RuPaul’s guest episode — but it’s the cowlicked ‘Glamazon Marge’ we’re really here for.

Smithers gets a boyfriend: ‘Portrait of a Lackey on Fire, – season 33, episode 8 (2021)

Disheartened by Mr. Burns’ lack of reciprocal feelings, Smithers starts a relationship with famous fashion designer Michael de Graaf. The pair would later appear on the cover the Attitude March/April 2022 issue.