1. The Sopranos gets in on the ground floor of a new TV age (January 10)

The HBO revolution was already underway in January of 1999, but the gulf between Sex And The City and Oz and earlier, cruder “It’s not TV, it’s HBO” originals like Arli$$ widened permanently when Tony Soprano met Dr. Jennifer Melfi. What followed challenged accepted wisdom about serialization, scale, and cinematic imagery on TV. David Bianculli called The Sopranos “The first gotta-watch, gotta-love, Gotti-like TV series of 1999,” while Matt Zoller-Seitz reported in the pages of Tony’s hometown newspaper that “it shouldn’t work, yet somehow it does.” Garnering the most nominations of any show at the 51st Primetime Emmys, The Sopranos notched wins for Edie Falco’s complicated, conflicted portrayal of mob wife Carmela, and James Manos Jr. and creator David Chase’s script for the brilliant “College.” One of the first things Tony tells Dr. Melfi is “Lately, I’m getting the feeling that I came in at the end. The best is over,” but the wave of great TV kicked off by The Sopranos proved him wrong. [Erik Adams]


2. Jon Stewart takes over The Daily Show (January 11)

When the reins of Comedy Central’s then-frothy The Daily Show were handed over from Craig Kilborn to Jon Stewart beginning with the January 11, 1999 broadcast, few could have imagined the outsize impact on American politics (and American satire) the program would soon develop, thanks to Stewart’s push to harder-edged political comedy. By the time a 2007 study showed regular Daily Show viewers were better informed about national and international affairs (and viewers of Stewart’s most common target of scorn, Fox News, were among the least informed), it was already clear The Daily Show had reshaped the cultural landscape. The person most Americans trusted to give it to them straight wasn’t a politician, or even one of the mainstream journalists who often seemed unable to cut through the doublespeak of the officials they were covering: It was a late-night comic who had absolutely had it with hypocrisy. [Alex McLevy]


3. Family Guy and Futurama lead the new wave of primetime animation (January 31; March 28)

Futurama and Family Guy share a lot more than a medium—both animated series debuted in 1999 on Fox, and both would go through cancellations, appearances on other networks, and revivals in the following years. Both series emerged in the shadow of The Simpsons, though only Futurama shared a pedigree with that now classic animated sitcom. But in trying to break from the orbit of Fox’s previous cartoon hit, Futurama and Family Guy took very different paths: The former mixed sci-fi and workplace comedy with hilarious results, while the latter opted for non-stop gags and non sequiturs. We can debate their individual quality (though we think we’ve made our own preference clear), but there’s no denying that their overall success ushered in the next wave of primetime animated series, which would go on to take hold of Sunday nights on Fox under the programming banner of Animation Domination. [Danette Chavez]

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4. The McMahon family establishes WWE dominance (January 24)

WWE had more or less won the Monday Night Wars by 1999, its feud between good ol’ boy Stone Cold Steve Austin and corporate menace Vince McMahon (a.k.a. Mr. McMahon) having swept viewers away from the tiresome shenanigans of an nWo-dominated WCW. For McMahon, the IRL WWE CEO, that meant more McMahon all the time. His son, Shane, took on a larger onscreen role, leading villainous stable the Corporation (and, eventually, the Corporate Ministry). His daughter, Stephanie, engaged in an onscreen romance with Test before turning heel to side with Triple H. Even McMahon’s wife, Linda, got in on the shenanigans, appointing Austin CEO to spite her husband. But it was McMahon himself who dominated the year’s programming, winning the Royal Rumble, headlining pay-per-views, interfering in title matches, and, in an egregiously illogical turn of events, revealing himself as the “Higher Power” behind the Corporate Ministry. It all worked, if only because McMahon’s shadow wasn’t yet long enough to obscure talent like Austin, The Rock, Chyna, Mankind, Kurt Angle, and Chris Jericho. It did, though, establish an unsustainable pattern of McMahon-dominated entertainment that’s grown increasingly tiresome over the years, especially over the last few years of Shane-centric storylines. [Randall Colburn]


5. Teen movies storm the multiplexes (ongoing throughout 1999)

Teen movies have been around as long as there have been teenagers. But 1999 saw a new wave of movies geared toward restless adolescents that were also—pretty good? Teens’ discretionary spending power was at an all-time high in 1999, and these newly empowered consumers flocked to see films from both established studios and newer imprints like MTV Films, which brought both Election and Varsity Blues to the screen that year. Perhaps the most dominant thread that year was the post-Clueless run of teen romances based on classics of Western literature: The sparkling, affectionate Shakespeare riff 10 Things I Hate About You is the best of the bunch, but She’s All That, based on Pygmalion, and Cruel Intentions, a modern update on Les Liaisons Dangereuses, also made an impact. But 1999 also saw the rebirth of the teen sex comedy in the form of American Pie, whose raunchy sense of humor reinvigorated the boobs ’n’ boners demographic so well served by Porky’s and its ilk back in the ’80s. [Katie Rife]


6. Lauryn Hill cleans up at the Grammys, TLC leads a top 20 takeover (February 24; yearlong)

In February of 1999, Lauryn Hill took a much-deserved victory lap for 1998’s The Miseducation Of Lauryn Hill, leaving the 41st Annual Grammy Awards with both arms full of gleaming gold gramophones, including the first-ever Album Of The Year trophy for a hip-hop record. (Mind-bogglingly, only one other has been awarded the top prize since.) But when Hill’s retro-soul sensation “Doo Wop (That Thing)” was named Best R&B Song that night, its successor was already climbing the charts, leading a wave of women in the genre who would dominate radio that year. “No Scrubs” ended a four-year hiatus for TLC during which countless vocal groups popped up to make a bid for the Atlanta trio’s title. In ’98, it looked like Destiny’s Child might have already succeeded, but with third LP FanMail, T-Boz, Left Eye, and Chilli re-asserted their supremacy and solidified their legacy as the reigning girl group of the decade—and so far, the bestselling in American history. In addition to “No Scrubs” (notably co-written by members of Xscape), the Billboard Top 20 that year includes 702’s “Where My Girls At?” (co-produced and co-written by Missy Elliott), as well as “Heartbreak Hotel,” a FanMail reject for which Whitney Houston assembled her own trio with Faith Evans and Kelly Price. Monica and Brandy both appear with individual hits, as do Deborah Cox and newcomer Jennifer Lopez. And that’s to say nothing of the R&B influence fueling the overnight success of pop singers like Britney Spears and Christina Aguilera. [Kelsey J. Waite]

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7. In Oscar upset, Shakespeare In Love wins Best Picture over Saving Private Ryan (March 21)

In the run-up to the 1999 Academy Awards, no bet seemed safer than Saving Private Ryan winning the Oscar for Best Picture. Steven Spielberg’s unprecedentedly violent World War II spectacle was both the critical and commercial favorite of the year, a true movie event so popular that it seemed to singlehandedly spark a mass resurgence of Greatest Generation nostalgia. It was, in other words, a no-brainer for the Academy’s top prize. But though Private Ryan mostly dominated the evening, right up through Spielberg’s expected Best Director win, its hot streak came to a halt when Indiana Jones himself, Harrison Ford, tore open the envelope and announced that the Academy had gone instead with Shakespeare In Love, about the (fabricated) romance behind Romeo & Juliet. Back then, the unexpected win was held up as proof that Harvey Weinstein, who ran a very expensive Miramax awards campaign for Shakespeare, could buy Oscar glory. Today it still looks like the most shocking upset in award-season history, regardless of why voters really chose to forsake the grim frontrunner for a frothier alternative. [A.A. Dowd]


8. The Matrix mows down conventional action cinema with the speed of a bullet (March 31)

The Wachowskis’ blockbuster spectacle The Matrix may not have invented the technique of “bullet time” filming (though studio Warner Bros. was quick to snap up the trademark after the film’s massive success), but it was the cinematic pioneer that forever changed the landscape of American action movies, and made bullet time a seemingly omnipresent facet of pop culture that year, be it serious or deeply stupid. The kinetic blend of Hong Kong wire fu, fresh cyberpunk storytelling, and inventive (and painstakingly executed) fight choreography provided audiences with a dizzying new kind of sci-fi action. (One particularly well-timed “whoa” from Keanu Reeves didn’t hurt, either.) And with its black-leather aesthetic, the film stole the zeitgeist thunder from the much-ballyhooed The Phantom Menace, with a digital world far more plausible and appealing than the one Lucas’ creations wandered through. [Alex McLevy]


9. Future mega-memes “All Star” and “Smooth” top the charts (May 4 and July)

Somebody once told me, “Man, it’s a hot one.” With their triggering first lines, corny (yet catchy) music, and even cornier lyrics, it’s perhaps no surprise that Smash Mouth’s “All Star” and the Grammy Award-Winning 1999 Hit “Smooth” by Santana Feat. Rob Thomas Of Matchbox Twenty Off The Multiplatinum Album Supernatural (definitely its official title) spent some time at the top of the charts 20 years ago. What is surprising is the strange lives they’d live beyond their initial popularity. While “Smooth” would ultimately handily beat out “All Star” in the commercial and critical rankings, becoming, according to Billboard, the second-greatest hit of all time, both songs would, for better or worse, become dyed in a vat of the so-bad-it’s good irony/sincerity of Web 2.0 memeification, spawning endless disorienting remixes, T-shirts, and parody Twitter accounts in the years to come. [Laura Adamczyk]

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10. Star Wars reinvades pop culture, but The Phantom Menace can’t live up to the hype (May 19)

Avengers: Endgame fever was a mere sneeze compared to the epidemic of hype that greeted the first episode of George Lucas’ prequel trilogy, which ended the Jedis’ 16-year absence from movie screens, give or take a wildly successful (and unfortunately augmented) re-release. Television and print media saturated the market with free publicity. Trailers were so hotly anticipated that they boosted the box office of the films to which they were attached, and even inspired parody campaigns. Fans camped out at theaters a full month before tickets went on sale (this was just before online tickets became widely available), while a reported 2 million people blew off work to catch the movie on opening day. Given how fully The Phantom Menace dominated the public imagination and conversation in the run-up to its record-breaking first weekend, it was perhaps inevitable that it would come to be generally (though not universally) regarded as the epitome of a crushing pop culture disappointment. No film, even one without Jar Jar Binks and tedious tariff disputes, could have lived up to that much hype. [A.A. Dowd]


11. A debut short story collection becomes a runaway literary success (June 1)

Every few years, a new collection of short stories—by either an established (George Saunders) or up-and-coming (Carmen Maria Machado) author—will be consumed with the same fervency that the reading public usually saves for popular novels. It’s unclear just what kind of literary magic must combine to make it happen: At one point, being endorsed by Oprah was the golden ticket; winning a major award or three certainly doesn’t hurt; or perhaps the stories in question need only be impeccably written, deeply felt, and speak to the richness of the American experience. Twenty years ago that collection was The Interpreter Of Maladies, Jhumpa Lahiri’s 1999 book concerning the lives of Indian immigrants in America. It would go on to win the Pulitzer Prize for Fiction, among other awards, be translated into over a dozen languages, sell upwards of 15 million copies, and help the canon become a little less monochromatic. Pretty impressive for a debut book. [Laura Adamczyk]


12. Napster launches (June 1)

When Napster launched in June, it wasn’t anything new: There had been peer-to-peer sharing sites before, including sections of IRC and Usenet. What Napster had, though, was a slightly more user-friendly interface and the admiration of millions of college-aged kids who’d just gotten access to their own computers and Ethernet cables. Quickly, the site become the darling of dorms and the scourge of colleges, who found their networks clogged by mislabeled covers of “All Along The Watchtower.” Labels and ISPs quickly caught wind of the illegal endeavor, and effectively shut down the service a couple of years later. The genie was out of the bottle, though: Napster had opened a generation’s eyes to the ease of file sharing, and the idea that anyone would have to pay to own a song—let alone an entire album—was damaged almost beyond repair. [Marah Eakin]

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13. The Blair Witch Project finds sleeper success with a viral campaign, gets overshadowed by a bigger horror hit (July 16)

The Blair Witch Project was groundbreaking in multiple regards. The low-budget horror hit is generally cited as not just ground zero for the ongoing found-footage craze (despite a few mock-doc antecedents), but also cinema’s first true viral hit, thanks to an innovative online marketing strategy. The still-active Blair Witch website presented a carefully fabricated mythology, inspiring amateur detectives to share info and chase breadcrumbs; plenty of prospective moviegoers came to believe that the film’s horrors were authentic—a hoodwink perhaps only possible at this particular moment in internet history, when rumors could spread quickly across forums but before every available scrap of prerelease info on a movie was available at a mouse click. The campaign helped propel the film to big box office, and also to some major backlash from an unfazed peanut gallery. Two weeks after its release, The Sixth Sense opened wide and made an even bigger bundle on word-of-mouth, overshadowing Blair Witch’s success. [A.A. Dowd]


14. Latin pop storms the music charts (yearlong)

While there were definitely Latin-inspired moments in music prior to 1999, the pop culture landscape really experienced a seismic cross-cultural shift with Ricky Martin’s captivating 41st Grammy Awards performance of “La Copa De La Vida.” A month later Martin released the instant hit and TRL mainstay “Living La Vida Loca,” and what quickly followed was a wave of Latin artists who would take over the charts and forever shape the mainstream pop sound. Jennifer Lopez, Enrique Iglesias, Marc Anthony, and Carlos Santana became ambassadors of an era in American music where salsa beats reigned supreme and non-Latin artists truly recognized their Latinx fans for, in many cases, the first time. Though some might consider the Latin pop explosion short-lived, it led to the installment of the Latin Grammys and became a serious entry point for future Latinx crossover artists. It also led to a few shaky Spanish versions of songs from non-Latinx artists, but we can certainly recognize the effort. [Shannon Miller]


15. Woodstock ’99 goes up in flames (July 25)

Heat, overpriced water, the irony of commemorating “three days of peace and music” on a former military post: Woodstock ’99 raised red flags throughout its run. On the final night, those flags burst into flames. While Red Hot Chili Peppers headlined the festival’s East Stage, bonfires sprung up across Griffiss Air Force Base. “Holy shit, it’s Apocalypse Now out there,” frontman Anthony Kiedis remarked—and faster than you could say, “The horror, the horror,” the festival descended into chaos. Forty-four arrests were made, rapes were reported, millions of dollars of damage was done, and fingers were quick to point in the direction of a lineup heavy in then-trendy nü-metal—particularly a rowdy set from Limp Bizkit. Those who were there spent months scratching their heads about what occurred: As MTV News reporter Serena Altschul said in a “Year In Rock” retrospective, “That’s the big question of the year: Why? And I haven’t seen anyone answer it, sufficiently.” [Erik Adams]


16. Who Wants To Be A Millionaire? changes the game-show game (August 16)

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On August 16, 1999, Regis Philbin bounded out onstage to introduce the game show Who Wants To Be A Millionaire?, which was already a hit in the U.K. ABC then pushed the trivia show every night for two solid weeks, entering “phone a friend” and “life line” into the annals of U.S. catchphrases. Millionaire was not only the first to offer that seven-figure cash prize, but it also helped reestablish the game show in prime time, as it had been primarily limited to daytime or pre-prime time TV for several years before that. It took a few months (until November) for a contestant to actually become a millionaire, but the now-hooked audience didn’t seem to care. The American Millionaire endured, on the network and later in syndication, for the next 20 years, ending its run in May 2019 with Bachelor host Chris Harrison asking the all-important question: “Is that your final answer?” [Gwen Ihnat]


17. Tony Hawk’s Pro Skater franchise launches (August 31)

Skateboarding was always cool, but it became much more accessible in 1999 when Activision released Tony Hawk’s Pro Skater for the PlayStation—easily the greatest skateboarding game of all time (until its sequel) and featuring an excellent, era-defining soundtrack. The brilliance of THPS wasn’t that it perfectly captured the sport, though; it’s that it captured an unrealistic fantasy version of the sport where you could ollie a dozen feet into the air and move your body faster than any human possibly could. Its effect was felt immediately, with every other studio shoving knockoffs out the door as fast as possible, and it kicked off a decade-long trend of “extreme sports” video games (none of which were remotely as good as Tony Hawk). [Sam Barsanti]


18. Sega Dreamcast gets caught between console generations (September 9)

Who killed the Dreamcast? Sega fans have been asking after the death of the company’s last (and pluckiest) console for a generation now, but it’s still unclear. Was it Sony, whose competing PlayStation 2 promised big but delivered late, grabbing consumer attention (and cash) in an increasingly crowded console market? Was it sports game mega-giant EA, which refused to furnish instant hits like the NFL Madden series, games that would have been obvious fits for the Dreamcast’s then-revolutionary built-in modem? Or was it Sega itself, which had spent the last five years burning bridges, pissing off partners, and insistently shooting itself in the foot with the ill-fated Sega Saturn? In any case, the Dreamcast—a budget-priced, online-enabled darling packed with games culled from Sega’s first-class arcade developers (and beyond)—probably never stood a chance; trapped between two generations of consoles, it died a few years later as a fondly remembered footnote, and marked the final retirement of one of the great early combatants in the console wars. [William Hughes]


19. Medal Of Honor kicks off an invasion of World War II-based shooters (October 31)

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It’s strange to think now—after roughly a million virtual D-Days have pounded the digital sands of Northern France’s beaches in series ranging from Call Of Duty to Battlefield and beyond—that realistic depictions of World War II in video games were once solely the purview of strategy players, watching the action safely from afar. That changed with Medal Of Honor, which boasted a ridiculously over-qualified cast of creators—most notably a fresh-off Saving Private Ryan Steven Spielberg, but also Michael Giacchino, back in his pre-Oscar-winning composer days—to create the first real attempt at a first-person WWII that didn’t also feature a bunch of pixelated mecha-Hitlers running around. Amazingly, the first MoH didn’t include a Normandy scene (that wouldn’t show up in the series until 2002) but it set a template that dozens of like-minded games would follow, marking a milestone in gaming’s pretensions to verisimilitude in the process. [William Hughes]


20. Kevin Smith’s Catholic comedy Dogma ignites religious protests (November 12)

It’s wild to think that, once upon a time, a Kevin Smith movie could contain anything so relevant as to hit a genuine nerve in society, but such was the case with Dogma, a comedy starring Matt Damon and Ben Affleck as renegade fallen angels who exploit a biblical loophole to worm their way back into heaven. The Catholic League and the American Society For The Defense Of Tradition, Family And Property were apoplectic over the movie, shrieking in fliers that Dogma “mocks everything we hold sacred” and “condones what we condemn—murder, obscenity, violence, profanity, drugs, drunkenness and rebellion!’’ An outgrowth of the right wing’s moral grandstanding in the wake of the Monica Lewinsky scandal, the protest could also be said to serve as a preamble of sorts for the bug-eyed evangelicalism of the George W. Bush era. Now, this kind of moral outrage looks as ridiculous as a 2019 Jay And Silent Bob reboot, what with these same protest-happy idiots now kissing the filthy feet of Donald Trump. [Randall Colburn]


21. The end of the year brings Y2K panic (December 31)

Was Y2K a disaster averted, or nothing but hype? Until the engineers who spent billions of dollars behind the scenes making sure that the world’s computer systems didn’t collectively freak out when the date changed from December 31, 1999 to January 1, 2000 come forward, we may never know. One thing that is clear, though, is that whether or not the problem was real, it was certainly profitable for conspiracy-minded opportunists. That applies not only to the survivalists who turned their attentions toward writing quickie books about Y2K and selling Y2K survival kits, but also toward the 24-hour cable networks that blew up a relatively obscure (if menacing-sounding) computer glitch into a full-blown crisis. Soon, millions of people worldwide were convinced that airplanes would fall from the sky, pacemakers would stop working, prison doors would swing open, and the world’s entire stockpile of nuclear weapons would self-launch once the clock struck midnight on January 1, 2000. Of course, the American government didn’t help, as its Y2K For Kids and Year 2000 Rumors websites planted seeds in paranoid citizens’ imaginations under the pretense of answering questions. Some stubbornly continued to believe that Y2K was a crisis after January 1, 2000 came and went, with one Y2K “doomer” posting on a message board, “Please be reminded that there are still 12 months left in this year.” [Katie Rife]