8. An unusual episode deconstructs the early-'90s cinema of deconstruction ("22 Short Films About Springfield," 1996)
For movie buffs, the early '90s were a great time to hit the arthouse, with American independent cinema as lively and entertaining as it had ever been, and formally innovative yet still accessible films drifting over from the UK, France, Australia, Spain, Japan, and elsewhere. "22 Short Films About Springfield" takes its title from the popular Canadian art film Thirty-Two Short Films About Glenn Gould, but its content riffs on Quentin Tarantino and the contemporary vogue for nonlinear narratives. Ironically, The Simpsons' parody of postmodernism ends up outstripping its targets, as the jumble of theme songs, blackout gags, and elevations of minor characters to lead status accomplishes everything po-mo sets out to do—and with better jokes.
9. Apu almost gets deported ("Much Apu About Nothing," 1996)
Springfield's most beloved immigrant faced deportation after Springfield voted to pass Proposition 24, a mirror of California's real-life Proposition 187 initiative, which sought to deny illegal immigrants access to government services such as education and medical aid. In Springfield, Prop. 24 meant all illegals (including Apu, Willie, Bumblebee Man, and even Moe) had to—as one protestor's sign read—"Get Eurass Back To Eurasia." It all came as a result of some slick sidestepping by Mayor Quimby, who blamed immigrants for the town's high taxes after instituting a costly (and completely unnecessary) "Bear Patrol."
10. Lisa joins an all-male military academy ("The Secret War Of Lisa Simpson," 1997)
In 1995, following a protracted legal battle, Shannon Faulkner became the first female cadet enrolled at The Citadel, a military college in South Carolina. It was national news at the time, even more so when she dropped out a week later. In "The Secret War Of Lisa Simpson," which aired in May 1997, one of Bart's pranks lands him at Rommelwood Military Academy (motto: "A tradition of heritage"). During a tour of the academy, the chronically academically unchallenged Lisa is impressed by Rommelwood's academic rigor, and demands to enroll. Like Faulkner, she's tormented by her fellow cadets, but unlike Faulkner, Lisa succeeds. But Faulkner opened a door that women entered at The Citadel and other military academies.
11. Springfield joins a cult ("The Joy Of Sect," 1998)
On March 26, 1997, 39 members of the Heaven's Gate cult committed suicide, which they thought would send their souls to a spaceship concealed by the Hale-Bopp comet. Just under a year later, The Simpsons aired "The Joy Of Sect," where Homer gets duped into joining a shadowy group called The Movementarians. Led by the mysterious Leader, the group plans to travel via spaceship to a planet called Blisstonia. Unsurprisingly, the whole thing turns out to be a money-making scam by a low-rent conman. The episode also references shadowy sects such as Scientology, the Moonies, the M.O.V.E. group, and organized religion in general: As Bart says, "Church, cult, cult, church. So we get bored someplace else every Sunday."
12. Bart gets medicated for a behavioral disorder ("Brother's Little Helper," 1999)
The '90s saw a dramatic increase in diagnoses of ADHD and other behavior disorders, and troublemaking students who were previously written off as hyperactive assholes were showered with awesome drugs like Ritalin and Adderall. Following a particularly epic prank, über-brat Bart is prescribed Focusyn, which almost immediately gives him "the urge to straighten up and fly right." A schoolyard conversation suggests that the general populace of Springfield Elementary is similarly medicated, from Milhouse's Clairton to Martin's voice-lowering hormones to Nelson's shock collar. While the new Bart is an initial success ("He's gone from Goofus to Gallant, and we owe it all to mind-bending pills," exclaims Homer), he rapidly deteriorates into a foil-hatted paranoid, intent on taking down Major League Baseball's spy satellite, a feat he accomplishes by breaking onto an Army base and stealing a tank. A horrified Marge swears off dangerous drugs, vowing to give Bart "nothing but fresh air, lots of hugs, and good old-fashioned Ritalin."
13. The presidency gets destabilized ("Sunday, Cruddy Sunday," 1999)
By the time this episode aired on Jan. 31, 1999, the nation had endured more than a year of the Clinton-Lewinsky scandal. The episode debuted a month after the House impeached Clinton, but less than two weeks before the Senate's impeach/acquit vote, so an air of uncertainty lingered over an otherwise lightweight episode about Homer organizing a Super Bowl trip. The show's long production lead time meant the episode would be nearly finished by the time Super Bowl teams were decided. So, in a funny bit of stunt animation, Homer, Moe, and Homer's friend Wally discuss the game, but conceal their mouths with mugs while mentioning team names, which were obviously dropped in at the last minute. Wally says, "Yeah I hear President [lifts mug] Clinton is gonna be watching with his wife, [lifts mug again] Hillary." Later in the episode, when Clinton calls to congratulate the victors from the Oval Office, he's distracted by Al Gore measuring a window. "Al, do you have to do that right now?"
14. The dot-com bubble bursts ("I Am Furious (Yellow)"), 2002
By April 2002, the dot-com bubble of the late '90s had been popped for a couple of years, taking with it myriad Internet start-ups. A sobering soul-searching settled in their place, which The Simpsons captured in this episode about Bart creating a popular Internet cartoon called Angry Dad. Touring the laid-back start-up that hosts the cartoons, Lisa asks head honcho Todd Linux about their business model. "How many shares of stock will it take to end this conversation?" he retorts. Lisa asks for two million, which Linux grabs from a paper-towel dispenser. When Bart and Lisa return later, the company has gone bust, and Linux is stealing copper wire out of the walls. When Lisa explains to Bart that the bubble burst, Bart is visibly shocked: "Bubbles can burst?!"
15. Gay marriage comes to Springfield, ("There's Something About Marrying," 2005)
Mere months after President Bush sidled back into the White House atop a shiny platform of "moral values," The Simpsons took on one of the hottest of the hot-button issues, as Springfield, in an effort to promote tourism, legalized same-sex marriage. Prior to its airing, word spread that a major character would also come out during the episode, sparking a who-shot-Mr. Burns-style debate among the nerd corps. The revelation that Patty Bouvier was a lesbian wasn't particularly earth-shattering, but it did provide for a nice twist when the previously pro-gay-marriage Marge disapproved of her sister's new lifestyle. In spite of the lead-up publicity, the episode lacked the heft to live up to the hype—particularly since Fox chose to precede it with the disclaimer, "This episode contains discussions of same-sex marriage. Parental discretion is advised."
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