The List – Best Latter Era Episodes of “The Simpsons”

Image from Fox.

In their 2016 book TV: The Book, critics Matt Zoller Seitz and Alan Sepinwall declared The Simpsons to be the best American television show ever made, and also argued in favour for the later years of the show being way better than anyone remembers. It’s true that the show has never returned to its stratospheric heights of the first ten years, but when you made the most influential television show of all time, the fall downwards, however small, seems much bigger from the top.

There were some truly terrible seasons of the show around 14 to 17, but now, as the show begins wrapping up its 28th season, it’s been through something of a renaissance, thanks to co-executive producer Matt Selman. The format remains the same but there’s been more experimentation with style and story, most clearly exhibited with their guest animator couch gags, featuring work by Sylvain Chomet, Don Hertzfeldt, Bill Plympton, and even Guillermo del Toro. The show has opportunities to be weirder and darker in ways it couldn’t do so much during its prime. In short, The Simpsons is now able to do whatever the hell they want, and I relish it.

Still, I’ve always been something of a defender of the “bad” years of The Simpsons, because even at its lowest, there were still glimmers of greatness to be appreciated. What those years lack in consistency, they make up for in variety.

To keep this list relatively easy to define, I am limiting the latter era Simpsons episodes to the period of time following what is generally considered the show’s peak, so only episodes from season 11 onwards will be included here. Treehouse of Horror episodes will not be included because even people who don’t watch the show now still watch those episodes and their format allows for changes and ideas the canon of the show itself does not.

Season 11, Episode 3: “Guess Who’s Coming to Criticize Dinner?” Homer has had enough jobs in his lifetime to keep any unemployment office busy, but the decision to have him work as a food critic is so perfect that I’m shocked it took a decade to happen. After essentially walking into the gig, Homer struggles to verbalise his love of food beyond his trademark grunts, so Lisa provides the words necessary. His gleeful enthusiasm for everything he eats doesn’t go over well with his fellow critics, who tell him to be meaner, which he, as always, takes too far.

Season 11, episode 12: “The Mansion Family”: The show has always relied on outlandish premises to fuel their stories, and rarely has it been as joke heavy as it is when the family are tasked with house-sitting for Mr Burns while he does for a medical check out. The Mayo Clinic scenes themselves are hysterical, while Homer’s giddiness at living as a rich man leads to drunken lawnmower driving, yacht adventures with Chinese pirates, and a good old fashioned box social. This is prime John Swartzwelder territory, with the jokes flying thick and fast.

Season 12, episode 18: “Trilogy of Error”: This is the episode writer Matt Selman considers his best work, and it certainly makes a case for his incredible comic skill, balancing top sight gags with an impeccably executed pastiche of Run Lola Run. It may be the highlight of its season too.

Season 13, episode 10: “Half Decent Proposal”: Jon Lovitz has guest starred on the show a number of times, including as Marge’s diva musical director and his character from The Critic, but he gets to be his slimiest as Artie Ziff, the ex-boyfriend of Marge who got too handsy at prom and never got over her. This Indecent Proposal parody isn’t exactly timely but has some of my favourite gags – Homer’s snoring is hysterical – and throwaway moments with people like Lenny.

Season 15, episode 3: “The President Wore Pearls”: The Simpsons has always been adept at musical numbers and genre parodies, and the two are combined for a toe tapping take on Evita, where Lisa becomes student body president, but is unaware that the teachers merely intend to use her as a scapegoat. All the beats of Andrew Lloyd Webber’s musical are here, with music that evokes his tunes while never completely copying them. Alf Clausen, the show’s musical director, is one of the hardest working and most under-appreciated people working in TV.

Season 18, episode 10: “The Wife Aquatic”: This episode has some of the best animation of the latter years, after the move from hand-drawn to computer styling. Loaded with references, jokes and sight gags, this story of nostalgia and a parody of The Perfect Storm takes the old school environmental fable and turns it on its head for a delightfully dark ending.

Season 19, episode 10: “E Pluribus Wiggum”: Politics has always been a target for mockery from the liberal-leaning show, and in this episode where Springfield becomes the first city in the country to hold primary elections, the jokes come thick and fast, with network neighbours Fox News and the castle-dwelling Republican Party getting their fair share of lampooning. And hey, it’s hardly unfeasible nowadays that Ralph Wiggum would become President, right?

Season 21, episode 19: “The Squirt and the Whale”: Even this late in the game, The Simpsons can still pack one hell of a emotional punch. While the second half doesn’t meet the expectations set by the first half, watching Lisa’s befriending of a doomed beached whale creates surprising empathy for the pair of them, which pays off big time in an unexpected way.

Season 22, episode 11: “Flaming Moe”: The subject of Smithers’s sexuality, and his barely concealed love for Mr Burns, is something the show has joked about almost since the beginning, in a manner that often came across as gay-bashing and childish. One of the benefits of the latter-era of the show is it has time to offer penance and creatively tackle the topic in a way they never could have gotten away with in the early 90s on a major network. Moe goes into business with Smithers, turning his bar into a welcoming gay establishment for the less trendy members of Springfield’s LGBTQ community, which leads people to assume Moe himself is gay. He briefly goes all Harvey Milk, but the focus is more on satirising gay panic than just laughing at gay characters. It also features an emotional high point for the gloriously pathetic Moe, and a chance for both Hank Azaria and Harry Shearer to put in some of their best voice work in years.

Season 23, episode 6: “The Book Job”: Anyone who’s ever read or blogged about the publishing industry will find a veritable smorgasbord of gags here. After Lisa discovers her favourite book series is ghost-written by a group of publishers – similar to the Animorphs series – Homer and Bart recruit a team to put together the most profitable kids’ series ever. Part publishing satire, part heist story, this is The Simpsons at its strongest in the latter years, and also has a gut-busting guest role from author Neil Gaiman.

Season 27, episode 4: “Halloween of Horror”: The first time the show ever does a non-Treehouse of Horror episode, and it’s easily one of their best, one that could stand shoulder to shoulder with the show in its prime. As Lisa begins to find Halloween too scary, Homer must look after her as intruders break into their home. This is the first time the show has aimed for genuine scares, and it’s a truly unnerving episode, playing around with horror tropes and imagery to both mock them and use them for effectively chilling mood. It’s also loaded with laughs, including the funniest Rocky Horror parody in decades.

Season 28, episode 6: “There Will Be Buds”: As lacrosse becomes the new sport of favour for the kids of Springfield, the ever pathetic Kirk Van Houten finally gets a chance to be the hero. Unfortunately for Homer, the man proves to be even more irritating than himself, and their one-sided friendship can only last for so long. On top of looking gorgeous – the animation and colours here are glorious – this is a rare episode with no sub-plots, allowing writer Matt Selman to fully explore the myriad of ways in which Kirk grates on Homer, even as he elevates the kids’ team to victory. Overall, this is a great example of Selman’s work and why he really should be running the show full-time. Not only are his episodes consistently funny, his focus on character, the thing that made The Simpsons so great in the first place, has revitalised the show with a renewed sense of creativity and style. With stuff like this in the show’s future, long may Springfield’s first family reign.


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