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!"
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