By the time season five of The Simpsons rolled out, the show was already on its way to being a cultural phenomenon if it wasn’t already. The series was cooking on all cylinders at this point. The fifth season featured the show’s 100th episode and this was the season that Conan O'Brien found out he was going to be hosting his late-night show.
This featured a string of guest stars like astronaut Buzz Aldrin, Beatle George Harrison, The Ramones, Kelsey Grammer, and the incomparable Phil Hartman. Here are the 10 best episodes of season 5, ranked according to IMDb.
Sweet Seymour Skinner’s Baadasssss Song - 8.4
In the show’s 100th episode, Bart inadvertently got Principal Skinner fired after bringing Santa’s Little Helper to school. Feeling bad for the mishap, Bart befriends his former nemesis but despite regaling Skinner with stories of how poorly Flanders is as the new principal, Seymour re-enlists in the army.
Flanders is removed from duty after mentioning the good lord in school. The episode also features Bart and Skinner coming to an understanding of mutual respect before taping a “Kick Me” and a “Teach Me” sign to each other’s back.
Homer’s Barbershop Quartet - 8.5
The fifth season premiered in a huge way, by featuring guest star George Harrison, and why not? The saga of the Be Sharps, Homer’s Barbershop Quarter mirrors the rise of British rock gods.
Homer, Apu, Barney, and Skinner hadn’t played together in years, but after finding an old LP, Homer regales Lisa & Bart with the story of Be Sharps as they gear up for a Moe’s Tavern rooftop concert.
The Last Temptation Of Homer - 8.5
The sultry Michelle Pfeiffer guest stars as Mindy, a new employee at the Power Plant with the hots for Homer. Meanwhile, Bart has to get new glasses and see a dermatologist making him look more and more like a nerd and a subject for bullying.
Homer tries to convince himself that Mindy doesn’t want him, but they have the same interests and Marge’s sickness is making her unattractive. But despite it all as always, the big oaf stays faithful to his blue-haired gal.
Homer Goes To College - 8.6
In writer Conan O’Brien’s last episode, Homer causes a nuclear meltdown and is required to head back to school. Cue up references to college favorites like Animal House and Monty Python.
Despite three “nerds” who try to help him earn a degree in Nuclear Physics, Homer winds up getting his new friends expelled from school. Now living with the family, they still help Homer get his degree but eventually have to hack into the computers and rig the grade despite Homer cramming for the test.
$pringfield (Or, How I Loved To Stop Worrying And Love Legalized Gambling) - 8.6
After Burns is able to legalize gambling in Springfield, the family gets in on the action. Homer becomes a Blackjack dealer while Marge unfortunately gains a gambling problem. Since Bart’s too young to go to the casino, he opens one of his own in the Simpson treehouse. Meanwhile, Mr. Burns becomes obsessed with germs and secluded himself - Howard Hughes style.
Boy Scoutz N The Hood - 8.7
After getting severely inebriated from a Squishee, Bart realizes that he’s joined the Junior Campers. He and Homer, along with other Junior Campers wind up stranded at sea during a trip gone wrong.
Meanwhile, the other campers are led to supposed safety by Ernest Borgnine, but it’s possible that Jason Voorhies slashed them all to bits. Despite having no real camping skills, Homer was able to lead himself, Bart, Flanders and Rod safety.
Treehouse Of Horror IV - 8.8
The Simpsons Halloween specials are almost always instant classics and the fourth installment is no different. With Bart dressed as the incomparable Rod Serling, he delivers three tales ala Serling’s lesser-known Night Gallery show.
The episode parodied Bram Stoker’s Dracula with Burns stepping into Gary Oldman’s crazy wig. A gremlin tries to take out Springfield’s kids in “Nightmare At 5 and 1/2 Feet,” playing off the iconic Twilight Zone, “Nightmare At 20,000 Feet.” The show’s best installment is the first though - “The Devil And Homer Simpson,” where Homer has to contend with his worst fear, the devil; and he's Flanders.
Rosebud - 8.9
Obviously a reference to the iconic Citizen Kane, “Rosebud” focuses on Mr. Burns’ own “sled,” in the form of his childhood teddy bear - Mr. Bobo. After moving from Burns to Lindbergh and even Hitler, the bear gets encased in ice and winds up back in Springfield where Bart buys it at the Kwik-E-Mart and gives it to Maggie. Despite his most vile efforts to get it back, Maggie won’t budge and Homer defends his baby. She finally gives it to him and sometimes in the distant future, a cybernetic Burns once again reunites with a decrepit Bobo.
Deep Space Homer - 8.9
Despite even series creator Matt Groening having reservations about telling such a grandiose story, The Simpsons still sent Homer up into space.
It also gave the creative team the chance to parody 2001: A Space Odyssey as “The Blue Danube” plays while Homer floats around the shuttle eating chips, and using “Sunrise” from “Also Sprach Zarathustra.”
Cape Feare - 9.2
When Sideshow Bob shows up, the Simpsons becomes cartoon lunacy as the disgraced clown constantly tries to kill Bart. In a spoof of the film, Cape Fear, the Simpsons delivered “Cape Feare.”
This episode featured the now-iconic scene with Bob stepping on rakes all over the place. After stalking the family to their new home in Witness Protection, Bob is about to succeed in ending Bart. But his penchant for singing show tunes, and the kids’ ingenuity always get the better of him.