What’s five out of 300?

In celebration of The Simpsons’ 300th episode, five Oracle staffers pick their favorites, spanning the show’s 13-year history.

Season 11, Episode 2:
Brother’s Little Helper

Bart is completely out of control in school. So much so that Principal Skinner calls in Homer and Marge for a conference, during which he convinces them that Bart should begin taking a new concentration drug called Focusyn.

At first Bart refuses to take the pills. After an attempt to catapult the pills into Bart’s mouth from across the living room, Homer, like any good father, tries a persuasion tactic.

“All your favorite stars abuse drugs. Brett Butler, Tim Allen …,” Homer tells Bart.

Marge eventually guilts Bart into taking the pills. In perhaps one of the lowest — but funniest — moments in Simpsons history, Bart emerges for breakfast the morning after his first dose. He says he’s experienced side effects: His testicles no longer fit in his underwear. The camera pans down and reveals the problem.

“Bart, get those oranges out of there,” Marge says, taking the oranges and returning them to her children’s lunchbags.

The show concludes when a mind-altered Bart proves that Major League Baseball is monitoring his every move in a high-tech marketing stunt.

Ryan Meehan

5,1: Homer’s Barbershop Quartet

Who would have thought Homer Simpson, with a voice like granite being churned through a vacuum, could help a music group win a Grammy, let alone an a cappella group? However, in “Homer’s Barbershop Quartet,” which originally aired Sept. 30, 1993, he did just that. This episode, which featured a guest appearance by George Harrison, has to be one the most fun to watch and find innuendoes and hidden jokes, especially if you happen to be a Beatles fan.

Matt Groening and his staff obviously did their homework on this cartoon version of A Hard Day’s Night that follows the B-Sharps, a barbershop quartet including Homer, Principal Skinner, Apu and Barney, to the top of their one-hit wonder career.

With spoofs on many famous Beatle moments, the episode culminates in one of the funniest scenes in Simpsons lore with the B-Sharps performing their final concert on the rooftop of Moe’s bar while Harrison drives by in a limo, rolls his window down, takes a look and proclaims, “Ah, it’s been done before.”

Michelle Demeter

5,2: Cape Feare

“Anyone who speaks German can’t be evil.” With those words from a parole board member, Sideshow Bob, Bart’s nemesis, is freed from prison and sets about his quest to kill the boy who sent him to the big house.

The Simpsons enter the Witness Protection Program, becoming the Thompsons (complete with a mid-episode Simpsons-style intro), though Homer takes some time to get accustomed to his new surname. The Simpsons/Thompsons move onto a house boat to avoid the calculating but bumbling Bob, who sports a tattoo with “Die Bart Die” on his chest at his parole hearing and passes it off as German for “The Bart The.”

The mop-haired felon encounters a series of painful pitfalls — such as getting stuck under the Simpsons’ car as they drive through a cactus patch and repeatedly stepping on rakes and getting hit with the handles.

Sideshow Bob doesn’t finish the job in the end, but Bart, and Simpsons viewers, has not seen the last of this character.

Khari Williams

6,6: Halloween Special V

Homer Simpson is an everyman character, and that’s why people love him.

But never did Homer so eloquently put into words the greatest fear of American men than during a famous sequence in The Simpsons’ fifth Halloween special.

“No beer and no TV make Homer something something,” he says.

“Go crazy?” Marge responds.

“Don’t mind if I do!” Homer says before screaming and launching into a tirade.

That great moment in Simpsons history occurs in the midst of a segment that plays on the Stephen King movie The Shining. The segment, called “The Shinning,” is a hysterical spoof on the widely popular film and comes in the midst of three ghoulish tales presented in a way that also plays off The Outer Limits television show.

The rest of the episode is hilarious, but it pales in comparison to that one brilliant scene. After all, many of us watched it with a beer in one hand and the remote in the other.

Rob Brannon

7,10: 138th Episode Spectacular

I enjoy it most when the writers mess with people’s heads. The episode “The Simpsons 138th Episode Spectacular” is a prime example of this. Using a clip show as cover, clips all shown that never existed before, such as a horribly animated clip that pokes fun at how The Simpsons looked in its first season. It is also hosted by Troy McLure (infamous for such Fox network specials as “Alien Nose Job”) and the blackboard joke is “I will only do this once a year.”

The show also sports a warning that it “only contains 23% new footage” and is therefore “Not a significant source of U.S. RDA original entertainment.”

The kicker, though, is McLure showing that if you freeze frame during the opening credits, the cash register that scans Maggie says “NRA,” after which he explains that this is “only one of the many right-winged references the producers hide in the show.”

Sebastian Meyer