1. The Krusty vs. Gabbo ratings war ("Krusty Gets Kancelled," 1993)

In early 1993, show-business headlines were dominated by the battle for late-night TV talk-show supremacy, as Jay Leno took over The Tonight Show, David Letterman prepared to make the jump to CBS, and former hot host Arsenio Hall saw his ratings plummet. The Simpsons spoofed the whole phenomenon with an episode that has heavily hyped ventriloquist's dummy Gabbo becoming a Springfield sensation and torpedoing the venerable, vulnerable Krusty The Clown. Bart and Lisa help organize a comeback special for Krusty, featuring Red Hot Chili Peppers, Johnny Carson in one of his few post-retirement "appearances," and Bette Midler, crooning to Krusty in a rehash of her farewell to Carson. The ultimate message: Showbiz legends trump flashes-in-the-pan.


2. The "I Didn't Do It" boy ("Bart Gets Famous," 1994)

In a gimmick-happy culture with a hummingbird's attention span, it doesn't take much to become famous in America, though those 15 minutes are up pretty quickly. That's the lesson of "Bart Gets Famous," in which Bart botches a walk-on role on a Krusty The Clown Show skit and becomes an instant sensation, spawning several albums and a biography that's mostly about Ross Perot (and contains excerpts from the Oliver North trial). Loaded with even more self-referential jokes than usual, the episode lampooned the phenomenon of disposable celebrities well before "celebreality" shows gave new life to has-beens. Now, it would be easy to see Bart's "I Didn't Do It" boy appearing on The Surreal Life, perhaps looking like the portly, stubble-faced male stripper/rock star/construction worker that he's often imagined to be in the future.

3. Homer goes to space ("Deep Space Homer," 1994)

One of the all-time great Simpsons episodes, "Deep Space Homer" slyly satirizes the dumbing-down of American culture, where the "blue-collar slobs" on Home Improvement or Married… With Children are more esteemed than nerdy astronauts. Then again, it also takes jabs at the space program, which had bottomed out since the Challenger disaster and could find few missions more significant than studying "the effects of weightlessness on tiny screws." As much as any episode prior to Frank Grimes' appearance three seasons later—and it's no mistake that the latter references the former, either—"Deep Space Homer" punctured the myth of modern America as a meritocracy, where good, hard-working people are the ones who get ahead. It really belongs to Joe Six-Pack and guys like Homer, who catch all the breaks, provided they aren't upstaged by that damned inanimate carbon rod.


4. Sideshow Bob runs for mayor with the help of a right-wing talk-show host ("Sideshow Bob Roberts," 1994)

The rise of Rush Limbaugh and the Republican takeover of Congress coincided with this episode, which finds Bart's old nemesis, Sideshow Bob, running for mayor of Springfield, aided by pudgy conservative talk-show host Birch Barlow—an obvious Limbaugh parody who urges listeners to "junk those Dumbocrats and their bleeding-heart smellfare program." Conservative viewers were so angered by the implication that all Republicans are evil, lying manipulators that many took to Simpsons newsgroups to chastise the show for "one of the most obscene efforts at mass character assassination in television history." Matt Groening found the response so amusing that he reprinted one such message a week later in his Life In Hell comic strip; it expressed a desire to see "Groening writhing in pain as he dangles by a section of his intestine from a tree."

5. That telltale Simpson DNA ("Who Shot Mr. Burns? (Part 2)," 1995)

Sometimes Simpsons writers have to seek out cultural reference points, and sometimes the stars align just for them. What are the odds that Homer and the gang would share a last name with the defendant in the tabloid-dubbed trial of the century? But the O.J. Simpson folly provided great fodder for the conclusion of the two-part "Who Shot Mr. Burns?", which narrows down the suspects thanks to "Simpson DNA" found at the scene of the crime. Such evidence seems rock-solid, but as Bart says, "positive ID, DNA… those won't hold up in any court." (In the clip show "The Simpsons' 138th Episode Spectacular," Troy McClure puts an even finer point on it: "Of course, for that ending to work, you'd have to ignore all the Simpson DNA evidence. And that would be downright nutty.")


6. Homer meets Generation X ("Homerpalooza," 1996)

There may be a more succinct commentary on Generation X than the following exchange between two disaffected youths attending an outdoor rock show in "Homerpalooza": "Oh, here comes that cannonball guy. He's cool." "Are you being sarcastic, dude?" "I don't even know any more." Throughout the episode, in which Homer tries to reconnect with a music scene that's long since left him behind, the writers explore the generation gap between classic and "alternative" rockers—one hopelessly out of touch, the other beaten down by irony and the corporate-sponsored rebellion of events like Lollapalooza. Still, Homer does appreciate bands like Smashing Pumpkins selling misery to today's youth: "You know, my kids think you're the greatest. And thanks to your gloomy music, they've finally stopped dreaming of a future I can't possibly provide."

7. Aliens run for president ("Treehouse Of Horror VII," 1996)

In this Halloween segment from election season '96, malevolent aliens Kang and Kodos conquer Earth by assuming the identities of Bill Clinton and Bob Dole. Newsman Kent Brockman sets the tone with "Welcome to Campaign '96: America Flips A Coin," and the faux-candidates do an excellent job of re-creating meaningless stump speeches. ("The politics of failure have failed; we need to make them work again.") And in the greatest summary of the American political landscape ever, faux-Dole interacts with a crowd thusly: "Abortions for all!" "Boo!" "Very well, no abortions for anyone!" "Boo!" "Abortions for some, miniature American flags for others!" "Yay!" The people vote Kang in anyway, enslaving themselves as adjuncts to wars they don't choose and know little to nothing about. Sound familiar? Everyman Homer speaks some truth: "These candidates make me want to vomit in terror!"


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."