It’s an inevitability that modern discussion of The Simpsons will bounce between themes of ‘then’ and ‘now’ – the series itself currently in the midst of its 26th season, their best and most zeitgeisty days long behind them. But it’s also a discussion that inadvertently diminishes the show’s cultural and creative significance, along with the astonishing brilliance it has brought audiences over the course of its long existence. To quote Don Draper, if you don’t like what’s being said, change the conversation. So here’s a rundown of six of The Simpsons’ finest half-hours…
Marge vs. the Monorail – Season 4, episode 12
Arguably the defining Simpsons episode. This is an aggressively funny ode to madcap absurdity, Springfield swindled by an all-singing, all-dancing monorail salesman. Away from the sheer number of gags, no other episode so well captures the strange mix of misplaced pride and earnest naivety that makes Springfield seem such a magical place.
Bart’s Girlfriend – Season 6, episode 7
The best Simpsons episodes feel lived-in, enhanced by what feels like real experiences that have been condensed into sitcom form and coloured bright yellow. Bart’s Girlfriend is every ‘nightmarish childhood romance’ ever, Bart crushing on Reverend Lovejoy’s charmingly evil daughter, Jessica. Voiced by Meryl Streep, I may add, in what is honestly one of her greatest ever performances.
Homer Badman – Season 6, episode 9
A bracing satire of American tabloid culture (never more memorable than in Homer’s edited-into-oblivion appearance on Rock Bottom), Homer Badman is also a notable testament to The Simpsons’ trademark three-act narrative structure, gliding seamlessly from candy convention goofiness to sexual harassment outrage to unexpected salvation in the form of Groundskeeper Willie.
Lemon of Troy – Season 6, episode 24
The greatest Simpsons episodes play almost like mini-movies, the show regulars banding together to thwart an outside threat or journeying away from Springfield for an out-of-state adventure. Lemon of Troy is rousing, heartwarming comedy at its finest, the Springfield kids tracking into eerie, incest-ridden Shelbyville to steal back the town’s precious lemon tree.
Summer of 4 Ft. 2 – Season 7, episode 25
Summer of 4 Ft. 2 is a love letter to youthful angst, the eternally isolated Lisa never more endearing as she tries to make friends while on vacation by altering her entire personality. This is heartbreakingly human, an episode delicately balancing exterior loudness with small, character-driven stakes. Plus, extra Milhouse!
You Only Move Twice – Season 8, episode 2
But of course the yuppie mogul promising the Simpsons a new glitzy life away from Springfield is a power-hungry supervillain. You Only Move Twice brilliantly signposts the various ways Cyprus Creek is slightly ‘off’ (daytime owls, weirdo new classmates, alcoholism), before spiralling into an elaborate James Bond pastiche at its close. It also delivers in Hank Scorpio one of the show’s most iconic one-shot guest characters.