The Simpsons: Every Episode Of Season Five, Ranked

Season four might be considered the best The Simpsons season of all time, but season five is pretty close. It lands slap-bang in the middle of what is commonly called the show’s Golden Era, and it’s easy to see why. Every character is perfect in just about every way, the storylines are genuinely engrossing, and the laughs just keep coming. At that point, it was almost impossible to see a world in which the show would deteriorate.

Obviously, there still has to be highs and lows, even in something wonderful. As such, we’ve used IMDb to rank every episode of season five from worst to best.

22 Lady Bouvier’s Lover (7.6)

One of the weaker episodes of season five focuses on a rarely used character, Marge’s mother, as she and Homer’s father start up a relationship that could lead to some very strange implications…

21 Bart’s Inner Child (7.7)

If there was one thing parents wanted to avoid when The Simpsons was airing, it was their children acting like Bart.

This episode encouraged the entirety of Springfield to do so.

20 Bart Gets An Elephant (7.9)

With a title like that, not much needs to be said about the content of the episode: Bart does indeed get an elephant. As one might well imagine, things do not go well…

19 Marge On The Lam (8.1)

In a semi-parody of Thelma & Louise, Marge and her new friend Ruth Powers end up in an exciting high-speed chase. We often wonder just where Ruth ended up eventually, we didn’t see much more of her.

18 Secrets Of A Successful Marriage (8.1)

Despite Homer and Marge having proven time and time again that their marriage is anything but successful, Homer starts to teach a class on how to have the perfect marriage.

17 Lisa Vs Malibu Stacy (8.2)

After Homer and Bart became the merchandisable main characters of the show in its first seasons, Lisa was left by the wayside. This episode was a reminder of how great she was.

16 Bart Gets Famous (8.2)

“I Didn’t Do It” became one of Bart’s most well-loved catchphrases very early on in the show.

After using it while on the Krusty Show, he was propelled to fame within the Simpsons universe itself, subversively mocking the show’s own use of catchphrases at the same time. Very meta, and a great moment in Simpsons history.

15 The Boy Who Knew Too Much (8.3)

It is rare that Bart is described as having too much knowledge. However, after seeing Mayor Quimby’s treatment of a waiter, he has to decide whether to save himself or turn Quimby in.

14 Homer And Apu (8.3)

Considering Homer visits the Kwik-E-Mark basically every day to stock up on beers, we don’t see much detail in his interactions with Homer.

Things change in this episode as Apu moves into the Simpson house. We miss him these days, but it makes sense that the character’s time had come.

13 Homer The Vigilante (8.3)

After a spate of robberies, Homer started a vigilante group with a team of people he has been involved with in just about every way possible, from singing to sport. They never seem to reminisce about their various social engagements, though…

12 Burns’ Heir (8.4)

In one of the many episodes that looks into who would end up with Mr. Burns’ fortune, Bart is chosen as the rightful heir to his estate. While Bart is just ten years old, there are a lot of parallels between their different approaches to evil.

11 Sweet Seymour Skinner’s Baadasssss Song (8.4)

It might not be the greatest name of a Simpsons episode ever, but it showed what happens when Ned Flanders ends up landing a teaching job.

Little did they know that this would become a regular fixture in the far future of the show when Ned took on a job at Springfield Elementary.

10 The Last Temptation Of Homer (8.5)

One of the many famous episodes detailing Homer and Marge’s romantic struggle while simultaneously demonstrating how unfalteringly in love they are. It’s all pretty wholesome when you think about it.

9 Homer’s Barbershop Quartet (8.5)

Homer tells the story—that we can’t believe had never been hinted at before—of when he achieved brief fame as part of a barbershop quartet in the 1980s. They might not look like a talented bunch, but they’ve got some serious pipes.

8 Homer Loves Flanders (8.5)

It’s best to describe Homer and Ned’s friendship as… rocky. Ned seems to care for Homer, while Homer hates Ned’s guts.

In this episode, however, Homer decides that Ned is his best friend, and their dynamic switches rather dramatically.

7 $pringfield (Or, How I Learned To Stop Worrying And Love Legalized Gambling) (8.6)

This episode put Marge in the drivers’ seat as a new casino leads to the introduction of her recurring gambling problem. She overcomes it here, but it becomes a recurring gag for years to come.

6 Homer Goes To College (8.6)

One doesn’t really expect someone with the intellect of Homer Simpson to have been involved in any formal education, but this episode forces him to attend college after it becomes clear he can’t do his job.

5 Boy Scoutz ‘n The Hood (8.7)

It’s hard to imagine anyone worse at being a part of a father-son rafting trip than Homer Simpson, but this episode serves as proof that even Homer can outdo himself at times.

4 Treehouse Of Horror IV (8.8)

The eighth installment of The Simpsons’ well-known horror special includes three stories, as per usual.

Homer sells his soul for a donut, Bart competes with a gremlin on the school bus, and the gang discovers that Mr. Burns is a vampire—par for the course, really.

3 Deep Space Homer (8.9)

“Deep Space Homer” might have been one of the first episodes to suggest that The Simpsons was running out of believable storylines, but it is also one of the show’s greatest ever triumphs. Non-stop comedy and some incredibly quotable lines fill this episode.

2 Rosebud (8.9)

Despite being the oldest character in the show, Mr. Burns ends up in a war-like stand-off with Maggie, the new owner of his Bobo doll. It’s one of animated TV’s finest MacGuffins.

1 Cape Feare (9.2)

The greatest Sideshow Bob episode of all time, and one of the best Simpsons episodes ever, is the phenomenally brilliant “Cape Feare.” Bob shows himself to be one of the best characters TV has ever seen and sets himself up as a primary Simpsons antagonist.