Film & TV

10 All Time Greatest Episodes of The Simpsons

Having been on TV without a substantial break since the end of the 1980s, there have been many, many episodes of The Simpsons, so picking out just ten classics means inevitably missing out on many others.

The show’s quality levels dropped off some time ago, so most of the best episodes come from the first 10 seasons, but given that so few rivals have managed even that incredible run of consistent genius, there’s still a lot to choose from.

Here our top 10 The Simpsons episodes ever:

10. Last Exit to Springfield (Season 4 Episode 17)

The joy of the early days of The Simpsons was seeing the writers tackle real-life issues rather than merely finding ways to shoehorn in guest stars, and this tale of unions, dental plans and business politics remains a timeless classic.

There are so many great bits, like the horrific British Book Of Smiles and the gas-induced Beatles hallucination, and it’s jam-packed with references to films like Batman, The Godfather Part II, Citizen Kane and How The Grinch Stole Christmas, meaning you can find new delights every time you watch it.

9. Duffless (Season 4 Episode 16)

One of the best Simpson-ized versions of a pop song features in this episode, Homer reminiscing about getting drunk to the tune of Frank Sinatra’s It Was A Very Good Year (Beer), and it’s another that faces up to a real issue and making it funny at the same time.

Homer’s attempts to avoid temptation are hilarious as they get ever-more ridiculous, while the science fair bits at the school are also fantastic, and the final scene’s Butch Cassidy homage is just lovely.

8. Marge vs The Monorail (Season 4 Episode 12)

Conan O’Brien is better known now as a talk show host, but he was also a Simpsons writer back in the day and this is his finest work.

A huckster called Lyle Lanley shows up in Springfield to flog his dodgy monorail and scams everyone mostly with a catchy song (“Monorail! Monorail! Mono-d’oh!”) and it also features a Leonard Nimoy guest appearance and Homer’s version of the Flintstones theme song.

It’s literally bursting at the seams with great ideas and gags.

7. Cape Feare (Season 5 Episode 2)

Long after The Simpsons finally stops being produced, it will be remembered for many things, and one of those will be Sideshow Bob standing on some rakes.

Written down like that, it doesn’t sound like a great deal of fun, but it’s one of those comedy moments that just works perfectly. You’re laughing just thinking of it, aren’t you?

This homage to Cape Fear is one of the best movie-inspired Simpsons episodes and the ‘Die Bart, Die’ license plate scene is the show at its ludicrous best.

6. The City of New York vs. Homer Simpson (Season 9 Episode 1)

This episode was seldom-seen for a few years after 9/11, understandably so since it is both comedically anti-New York and heavily features the Twin Towers.

Thankfully now it gets shown more regularly because nothing in it could cause offense or upset, and it’s got both some of the best jokes and some of the best songs (particularly I’m Checkin’ In) from the whole show to date.

And it’s got Woody Allen pouring garbage on Homer’s head.

5. Girly Edition (Season 9 Episode 21)

Three words – PRAY. FOR. MOJO. That’s almost all you need to know about this episode and it’s only the subplot.

Homer’s helper monkey Mojo is a classic character even for his very brief appearance, and his struggle to keep up with his master’s unhealthy lifestyle is hilarious.

The main plot is also pretty good too, seeing Bart and Lisa tackle the world of journalism and the perils of the Crazy Cat Lady (always a favourite).

4. Homer The Heretic (Season 4 Episode 3)

You have to wonder how much this episode has contributed to plummeting church attendances around the world, with so many people sharing Homer’s reluctance to swap a nice warm house and a TV for a chilly boring church.

It’s hard to disagree with his insistence to God that “I’m not a bad guy, I work hard, and I love my kids… so why should I spend half my Sunday hearing about how I’m going to hell?”

A great episode that tackles issues and has a shedload of classic jokes.

3. Homer at the Bat (Season 3 Episode 17)

Even for those of us who live in a country where baseball is a big deal, this is a classic episode and for those who don’t… this episode is still a classic episode

The Talkin’ Softball song at the end is an instant earworm as well as a surprisingly effective recap of the entire episode, but one of the best gags comes from Mr. Burns picking the players he wants to be ringers in his team, only for Smithers to point out they were all long dead (one having died 130 years earlier), just to re-emphasize the running joke about just how old Monty really is.

Most of all, it showed that you really can combine sports and a TV sitcom and get the best of both worlds.

2. You Only Move Twice (Season 8 Episode 2)

There are just so many great things about this episode, from the idea of The Simpsons going into the witness protection program as The Thompsons (complete with fake intro theme) to Homer working for a Blofeld-style Bond villain who is also the nicest boss you could possibly have.

Hank Scorpio remains one of the best one-off characters The Simpsons has had and both the plot and its many movie references and sight gags all add up to a Simpsons episode you could watch over and over again forever.

1. Homer’s Enemy (Season 8 Episode 23)

Sometimes The Simpsons could go really dark, and this episode is black humor at its finest, painting Homer Simpson in the least flattering light ever by introducing a rival at work in Frank Grimes, who is everything Homer isn’t – hard-working, diligent, conscientious – and best of all having Homer completely oblivious to their rivalry.

Without realizing it, he drives Grimes completely mad and contributes to his death at the end of the episode. Not everyone likes it, but it’s a great twist on the usual Simpsons fare.

Richard Hammond

I am the founder of 9Mousai and am deeply interested in creativity and what inspires it. My main passions are writing, film and music but I have huge respect for all the arts. I'm also an animal lover and have a little cat called Winston and enjoy the occasional whiskey or two...

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