Looking back at the '90s, for reasons that only Kurt Loder and Clarissa Darling may be able to explain, it isn't so much nostalgia that rekindles our fondness but the decade's outrageously cool attempts at reinterpreting the past. We often forget that the '90s were the first decade that mostly lacked artistic novelty, and whose most infamous filmmaker, Quentin Tarantino, was a shameless retrophile, while everything from Forrest Gump's dominance at the box office to the hacker movie and Valley Girl–inspired teen movie were retro.

The '90s were also all about the music. The decade's films gave us movie stars made famous in music videos (Alicia Silverstone bungee jumping in an Aerosmith video, to start) and introduced us to indie bands, like Radiohead in S.F.W. or techno music as the hacker's preferred genre. The '90s just took what the '80s created, with their music video–style sequences, and made them a bit cooler; relatable for an AOL generation jaded by grunge — too emo for rah-rah training montages and uncomfortably awkward dance-offs. 

The following — beginning at 23 as an homage to the decade's winningest person, Michael Jordan — is a meticulously ranked list of the most memorable moments when a song made a sequence so cool that it won an MTV Movie Award or started a trend. While the '80s had more memorable hits generated by songs' interplay in film, the '90s had iconic moments we continue to obsessively reinterpret and attempt to fashion our lives around.

23. Blink-182 – “Dammit”
Can't Hardly Wait [1998]
For the teen movie, the house party, along with prom night, was the genre's laziest (and oftentimes most memorable) cinematic technique to bring closure to shit. Can't Hardly Wait was an entire movie built around this concept, where Blink-182's “Dammit” comes on just as the cops show up to shut down the party. “Well, I guess this is growing up” is how a music supervisor narrates a stupidly simple high school comedy without a voice-over. —Art Tavana

22.  The Prodigy — “Voodoo People”
Hackers [1995]
If the history of the internet was a TED Talk and the cultural impact of Hackers was being discussed, the speaker would conclude that one film, by itself, made it offensively sexy to play with a computer. It also gave us Angelina Jolie, her CGI-style lips and the myth that it's better to code to electronic music. “Voodoo People” is the film's beating heart, the song we hear during a hacker battle between “Zero Cool” (Jonny Lee Miller) and “Acid Burn” (Angelina Jolie), which basically predicted online dating. —Art Tavana

21. R. Kelly — “I Believe I Can Fly”

Space Jam [1996]
A live-action cartoon based on Michael Jordan's pointless retirement and messianic return as basketball Jesus, Space Jam's mawkishly inspirational theme “I Believe I Can Fly” is how we, the audience, watch in awe as teenage Air Jordan shoots around in his backyard (contemplating flight) and then returns to Earth in a cartoon spaceship piloted by Looney Tunes. This movie is ridiculous, but with R. Kelly singing about taking flight in a cornfield, it's Field of Dreams for the “Be Like Mike” generation. —Art Tavana

Coyote Shivers — “SugarHigh”
Empire Records [1995]
Over the course of a single whirlwind day, the employees of an imperiled record store get up to all sorts of mischief. There’s head shaving, diet-pill popping, aging pop star–fucking, but it all wraps up with a triumphant vocal performance by Gina (Renee Zellweger), whose compulsive promiscuity is really just a symptom of her low self-esteem. Get her up on the rooftop with Coyote Shivers for a rendition of the somewhat generic power-pop jammer “SugarHigh” and she’s all wound up like a sexy baby having a tantrum. (This scene has always made me feel deeply, deeply uncomfortable for Zellweger, which is why I love it so awfully much.) The Empire Records soundtrack was full of choice, era-defining songs such as Gin Blossoms’ “Until I Hear It From You” and Edwyn Collins’ fuzzy, retro “A Girl Like You,” but sadly the version of “SugarHigh” included therein was Zellweger-free and kind of a letdown. And the soundtrack didn’t even have “Say No More, Mon Amour.” Way to ruin Rex Manning's day. (Fun fact: From 1992 to 1999, Coyote Shivers was married to former model and legendary groupie Bebe Buell, mother of Liv Tyler. So when Empire Records came out in ’95, a 30-year-old Shivers was Tyler’s stepdad. Cute!) —Gwynedd Stuart

Aerosmith — “I Don't Wanna Miss a Thing”
Armageddon [1998]
Director Michael Bay understood machismo better than any other filmmaker of his generation. The opening sequence of Bad Boys is basically car porn during a sunset. He took maleness, siphoned the shit out of it and somehow made countless blockbusters built around epic montages and explosions during sunsets. Armageddon was his most sensitive film: a story about a father protecting his daughter from a giant fucking asteroid. A power ballad by Aerosmith and Diane Warren scores the emotional pre-takeoff sequence, during a sunset, of course, and the closing wedding scene when Liv Tyler marries Ben Affleck while her real-life dad sings: “Don't wanna close my eyes, don't wanna fall asleep, cuz I miss you, baby, and I don't wanna miss a thing.” —Art Tavana

18. Cyndi Lauper — “Time After Time”
Romy and Michele's High School Reunion [1997]
A movie about young-adult angst that had a wildly successful original soundtrack that was actually pretty shitty: 11 popular hits from the '80s that were all, by 1997, played out and mostly reserved for shopping mall playlists. One song missing from the soundtrack provides one of the most earnest scenes in '90s cinema. Rubber magnate Sandy Frink — wearing Air Jordan–inspired ballroom kicks — dances with Romy and Michele to Cyndi Lauper's “Time After Time” in a choreographed ballet that was at once ridiculous and better than anything on Dancing With the Stars. —Art Tavana

 Hanz Zimmer — “You're So Cool”
True Romance (1993)
Zimmer's carefree calypso juxtaposes the gritty romance between Clarence, a comic book–store clerk, and a hooker named Alabama, every geek's dream girl. Titled after the film's most memorable line, “You're so cool, you're so cool, you're so cool,” the melody hypnotizes us during Alabama's poetic voice-over and quietly commands us to stay cool as the film feeds us Clarence's dangerous philosophy: “Rock & roll, living fast, die young and leave a good-looking corpse.” —Art Tavana

The Sundays — “Wild Horses” 
Fear [1996]
There’s no way Harriet Wheeler and co. could’ve dreamed their beautiful, sublimely twang-free cover of The Rolling Stones’ “Wild Horses” would be inserted — pun intended — into the most iconic finger-banging scene in ’90s cinema. The song’s dreamy strains begin as Nicole and David (Reese Witherspoon and Mark Wahlberg) board a roller coaster at a better-than-average carnival. He places his hand on her thigh — but wait! She’s got something more in mind. After some thrusting with David’s wrist at an unnatural angle, and just in time for both the song’s chorus and the ride’s zenith, Nicole achieves ecstasy. Before you praise the film’s sex-positivity, keep in mind that this is all a Lifetime-style cautionary tale to redouble a teen girl's anxiety that the boys we allow to take liberties with our purity will turn out to be criminally insane people who are also lazy spellers (“Nicole 4 eva” … c'maaan). Worse yet, it promised a sort of rapturous pleasure our boyfriends’ (or girlfriends’) digits couldn’t actually deliver. Good song, though. —Gwynedd Stuart

KISS — “God Gave Rock and Roll to You” 
Bill & Ted's Bogus Journey [1991]
The final scene in Bill and Ted's unpretentious journey to conquer the “Battle of the Bands” ends with KISS' “God Gave Rock and Roll to You.” It's a most epic set broadcast around the world as Bill and Ted's band, Wyld Stallyns, shred to restore peace to the world — with the Grim Reaper on bass — becoming the biggest band on the planet right in front of our eyes. The sheer epicness of the scene establishes the whole point of the Bill and Ted franchise: to sell us on the idea that Van Halen and babes are as crucial for survival as oxygen. This is also the most unashamedly anti-grunge scene during the rise of grunge. KISS were the perfect band to sell us on Bill and Ted's hard-rockin' worldview. —Art Tavana

14. The Flaming Lips — “Bad Days”
Batman Forever [1995]
Of all the original songs on the Batman Forever soundtrack (widely considered to be better than the movie itself), including Seal's No. 1 hit “Kiss From a Rose,” only three actually appeared in the film. The vague optimism of Flaming Lips' slacker classic “Bad Days,” a song most people discovered on this soundtrack, provides a bit of sunshine through the thick clouds of Elliot Goldenthal's score. It's also the unofficial theme of neurotic scientist Edward Nygma, brilliantly overacted by Jim Carrey, whom we see creating a riddle in his shitty apartment as he transforms into the Riddler. —Art Tavana

13. Neil Young's guitar

Dead Man [1996]
Jim Jarmusch's postmodern Western is scored by Neil Young's guitar in such a way that it makes every solo feel as if it's pushing William Blake further into native territory to meet his maker. Young's solos are minimalistic, wild and uncomfortably loud. Somehow the sound of jolting guitar riffs in the lonely, monochromatic West are kind of ridiculous. We often think of Ennio Morricone scores, or Disney's fictionalized “Old West” idealism when it comes to Westerns, but Neil Young brought rock & roll to the genre and made it fucking cool rather than outdated. —Art Tavana

Jim Carrey — “Somebody to Love”
The Cable Guy [1996]
This movie was dark and kind of sad, a buddy movie about a sociopath looking for a real friend. The film's psychedelic karaoke scene seems like a bonding moment, at first, but it's really Chip's (Jim Carrey) attempt at catching Steven (Matthew Broderick) in the act with another woman, and then using it as blackmail to coerce a friendship. All the creepiness of the karaoke scene often overshadows the fact that Carrey sang Jefferson Airplane's “Somebody to Love” like Johnny Rotten, dressed like Jim Morrison, in what became an MTV music video and the film's most memorable scene. —Art Tavana


11. Average White Band — “Pick Up the Pieces”
Swingers [1996]
For most of their 20s, men try to figure out how to pick up girls. This is a movie about just that, set during the ’90s swing revival, as a group of Hollywood rats tries to get laid and crack Wayne Gretzky's skull on Sega Genesis. It's Entourage before Entourage, or a more swinging Tarantino-style movie designed for proto-hipsters; it even has a scene that’s a direct nod to Reservoir Dogs, where guys sit around a table, debate mundane shit and then walk down the sidewalk in slow motion to a song from the ’70s. This was male cinema for a generation that grew up without online dating or feminism. —Art Tavana

10. Derek and the Dominos – “Layla” 
Goodfellas [1990]
There are lots of songs that sound as if they were made to become commercials — sue me, but The Who is a huge offender; see: “Bargain” — and then there are songs that were made to become cinematic scores. The outro to “Layla,” the quiet after a storm of guitar riffs, is an almost unreal fit for the gruesome scene in Goodfellas in which the guys who knew too much start turning up dead in cars and garbage trucks and refrigerated meat trucks throughout New York City. Even the movie’s music editor is into it. In a 2015 interview with Esquire, Chris Brooks said, “The last time I saw the film, which was a while ago now, I just thought, ‘Man, that's amazing.’” Of course, it’s Scorsese, so there’s narration laid over the bulk of the scene, but listen to the way the music picks up right as the doors to the meat truck swing open. Oh, but at least Tommy's being made … —Gwynedd Stuart

9. Geto Boys — “Die Motherfucker” 
Office Space [1999]
Mike Judge maybe doesn’t get enough credit for molding musical tastes in the ’90s to the extent that he did, from Beavis and Butt-head’s MST3K-style viewings of music videos through Office Space, a movie that perfectly captured a grown-up Gen Xer’s malaise. Watching three business-casual clad dudes beat the shit out of a copy machine to a hardcore rap song succeeded in being satire rather than appropriation thanks in part to Judge and his comedic and generational bona fides. —Gwynedd Stuart

Kenny Rogers and the First Edition — “Just Dropped In”
The Big Lebowski [1998]
Fargo is the best movie to be released in the 1990s. Says me and a few other people, I’m sure. But the Coen brothers really let their Old Hollywood fanboy flags fly in The Big Lebowski, one of the funniest films of the ’90s (says me and I’m sure a few other people). The “Gutterballs” montage not only introduced millennials to a much cooler, pre-Gambler Kenny Rogers but also brought classic music montages and dream sequences of recent decades to a new level. —Gwynedd Stuart

The Pixies — “Where is My Mind?”
Fight Club [1999]
Fight Club  is an anti-corporate cult film that reminded us to never use credit cards. It was initially only popular with indebted college kids, most of whom owned a bong and at least one Pixies CD. In the final scene, after we've discovered that Tyler Durden is really just a figment of the narrator's imagination, the unnamed narrator and Marla hold hands and watch every college kid's wet dream: buildings blowing up, credit card debt being reset and the sounds of a howling madman with a guitar as “Where Is My Mind?” plays, a song that's both manic and nostalgic. We're made to believe you can take on the system with your mind. —Art Tavana

Chris Issac — “Baby Did a Bad Bad Thing”
Eyes Wide Shut [1999]
Kubrick's Eyes Wide Shut was shot like a Champagne-induced holiday buzz, which made it both moody and extravagantly sexual. With such an aesthetic, Nicole Kidman gently rocking her hips in the mirror as “Baby Did a Bad Bad Thing” plays is deliciously steamy. When Tom Cruise nibbles at her neck, as Kidman's cold blue eyes watch herself getting off, it becomes the most stylishly sexy scene of the decade; it lasted less than 30 seconds and became the film's trailer, most memorable scene and poster. —Art Tavana

The Drifters — “White Christmas”
Home Alone [1990]
Kevin McCallister's hands-on-face scream is the most iconic moment, maybe, in the history of Christmas movies. Singing into a comb in his parents' bathroom — with his family having accidentally abandoned him to go on vacation — Kevin imitates a seasoned crooner as he sings “White Christmas.” We chuckle at his misguided adultness, which ends with a scream when he applies a Brut aftershave that burns his unshaven skin (as a man, I can tell you this is bad science). Then again, every single kid who saw Home Alone in the ’90s, when Macaulay Culkin was as big as The Beatles, re-enacted this scene in their parents' bathroom mirror. —Art Tavana 

Urge Overkill — “Girl You'll Be a Woman Soon” 
Pulp Fiction [1994]
Maybe the Jack Rabbit Slims twist-contest scene is more iconic, but this scene is better. Mia and Vincent arrive at the Wallace compound, enjoy a delicious silence — “I don’t know what that was,” Mia says — and Vincent goes to take a piss. Kudos to Nash Kato for doing Neil Diamond justice and goddamn, goddamn Uma Thurman can dance recklessly with a wig on, but the real joy for the viewer is knowing good and well what would've happened if she hadn't found that particularly potent heroin in Vincent’s jacket pocket. We know what happened to Tony Rocky Horror but we’ll never know why. Or what was in the briefcase. —Gwynedd Stuart

Stealers Wheel — “Stuck in the Middle” 
Reservoir Dogs [1992]
Tarantino's most underappreciated talent is his ability to make grotesque violence seem funny. In his first film, before anyone really caught on to his irony, the scene where Mr. Blonde pulls out his straight razor, turns on “K-Billy’s Super Sounds of the ’70s” and starts dancing to “Stuck in the Middle” confused us: Why is a gangster in cowboy boots dancing with a straight razor? Why are we giggling at the sight of a bloodied cop who's begging for mercy? It's hilariously constructed — like just about every beheading in Kill Bill Vol. 1 — so when Mr. Blonde slices off the cop's ear, it's exhilarating to watch. We don't even feel guilty. It was Tarantino's debut as Hollywood's most disturbing satirist, set to a Stealers Wheel song. —Art Tavana

The Muffs — “Kids in America” 
Clueless [1995]
The Muffs deserve better. 1995's Blonder and Blonder is one of the best pop-punk records of the decade. And yet, no matter how many times Kim Shattuck unleashes her trademark scream or releases a critically acclaimed punk-rock record, The Muffs will always be associated with the opening sequence from the decade's most vapid teen comedy about shallow teens: Clueless. Their cover of “Kids in America” plays as Cher (Alicia Silverstone) and her richie friends drive around in a white jeep, shop for shit, feed pretty boys strawberries and, like, wonder, “Is this, like, a Noxzema commercial or what?” Somehow Cher is earnest enough in her emptiness to make us love her, like she's just being herself, or because she's symbolic of the spoiled white girl that's as American as muscle cars. Clueless provides insight into teen America's retarded values, which makes a punk cover of “Kids in America” the appropriate theme song for Cher's hilariously corporate (and heartfelt) worldview —Art Tavana 

Queen — “Bohemian Rhapsody” 
Wayne's World [1992]
In an era when rock music was buried beneath a shroud of plaid flannel and emotion, Wayne’s World ripped it off and reminded us that there was still room for Queen’s theatrics and flamboyance. Besides that, it was the best of the SNL spinoff films, hands down. And as a recent Chicagoan, I’m happy to report that the Payless Shoes they drive past in the few few seconds (in what’s supposed to be in Aurora, but is actually at the Milwaukee-Diversey-Kimball intersection in northwest Chicago) is still open for business. —Gwynedd Stuart

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