92 items
The Omaha band that fused alt-rock, reggae, funk, and rap into a laid-back sound built for summer. Their 1995 self-titled "Blue Album" broke them nationwide on the strength of "Down" and "All Mixed Up," and their two-vocalist lineup has stayed intact for decades.
The Queens mixtape king who survived being shot nine times, got signed by Eminem and Dr. Dre, and turned his bulletproof origin story into one of the biggest rap debuts of the decade. For a few years in the mid-2000s, 'In da Club' and 'Get Rich or Die Tryin'' were everywhere, and 50 Cent was the most bankable name in hip-hop.
The boy band that built itself—assembled independently by four guys chasing the dream in Los Angeles, without a Lou Pearlman or corporate svengali telling them who to be. They cracked the charts with 1997's "Invisible Man," then spent 1998–2000 as Motown Records' R&B-leaning answer to the Backstreet Boys and NSYNC, delivering a handful of genuine hits including one number-one collaboration with Mariah Carey, then watched their moment fade when Nick Lachey married Jessica Simpson in 2002 and reality TV captured his afterlife.
The SNL goofball who became a box-office machine — Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy. In the '90s his man-child comedies and shouty voices made him one of the most bankable comedians alive.
The Canadian teen-pop star who reinvented herself as the voice of 90s female rage. Raw, oversharing, absolutely unapologetic about her feelings—she gave the decade permission to be a mess and call it art.
The Austrian bodybuilder who became the biggest action star on the planet. The Terminator made him iconic in the 80s; the early 90s — Total Recall, Kindergarten Cop, T2, True Lies — made him inescapable. The accent launched a thousand imitations, all of them affectionate.
The Canadian pop-punk singer who defined early-2000s teen rebellion with a necktie knotted over a tank top, chain wallets, and an I-don't-care-what-you-think attitude. Her 2002 debut Let Go crashed onto radio with "Complicated" and "Sk8er Boi"—instant anthems—and positioned her as the voice of a generation of mall-goers who wanted to be skaters but shopped at Abercrombie. Follow-ups Under My Skin and The Best Damn Thing kept her reign solid through 2007.
Orlando's harmonizing five-piece formed the template for late-90s teen-pop dominance. The Backstreet Boys' matching choreography and Lou Pearlman's boy-band machinery made them a TRL staple, an arena-tour juggernaut, and the answer to every teen magazine's "Who's your favorite Backstreet Boy?" quiz.
Pop-punk pioneers who mixed juvenile toilet humor with real melodic craft and suburban-teen honesty. From scrappy San Diego garage band to first punk album atop the Billboard 200. Their untitled third album was the moodier reinvention; the hiatus in 2005 felt less like goodbye and more like a pause in a story everyone knew would resume.
The jam band that actually broke through to Top 40 radio, with John Popper's lightning-fast harmonica as the most unlikely lead instrument of 1995. "Run-Around" logged a then-record 49 consecutive weeks on the Hot 100 and won a Grammy, and the Wizard of Oz video never left MTV.
The decade's most likable leading man: caveman in Encino Man, gentleman in School Ties, jungle king in George of the Jungle, and finally the revolver-twirling hero of The Mummy. Hollywood's nicest action star — and the comeback story the whole internet rooted for.
A former Mickey Mouse Club kid whose debut single '...Baby One More Time' (September 1998) and January 1999 album catapulted her to megastardom as the defining pop voice of the millennium. TRL countdown staple, Rolling Stone covers, Pepsi deals, and cultural omnipresence through the early 2000s with 'Oops!... I Did It Again' (2000) and 'Toxic' (2003–04).
The everyman action hero who proved you didn't need muscles the size of tree trunks to save the day. Bruce Willis went from TV comedy to Die Hard's John McClane, rewriting what a blockbuster lead could be—and spent the next decade proving it with an eclectic run of '90s classics that kept him in the conversation.
![Video thumbnail — Busta Rhymes - Woo-Hah!! Got You All In Check (Official Video) [Explicit]](https://i.ytimg.com/vi/EQzvQO2LcA4/maxresdefault.jpg)
The human cartoon of 90s rap—hip-hop's most watchable man, a blur of dreadlocks and rubbery limbs who moved like he was made of springs. Trevor Smith stole posse cuts for a living and built a solo career on being impossible to look away from.
The Prince protégée who became the late-90s everywhere-woman: Playboy covers, Baywatch's Lani McKenzie, MTV's Singled Out, and a Las Vegas wedding to Dennis Rodman that hit annulment papers nine days later. Then the 2000s spoof-movie wave made her its favorite good sport.
The Mickey Mouse Club grad who became the 2000s' designated voice—every critic conceded she could really sing, which was the whole point of the rivalry with Britney Spears. She went from a 1999 debut that shipped ten million records to the leather-chaps reinvention of Stripped, proving she was more than a pretty face with pipes.
The mole, the mane, the Pepsi. Cindy Crawford was the supermodel era's all-American face — MTV's House of Style host, Super Bowl commercial legend, and the reason a generation's living rooms had a workout VHS parked in the VCR.
A German blonde discovered in a nightclub who became the face on a thousand magazine covers, the muse of Karl Lagerfeld, and — reportedly — the highest-paid model in the world. Claudia Schiffer was the supermodel of the supermodel era.
Adam Duritz's dreadlocked, wordy, openly wounded alt-rock band — one of the definitive sounds of 90s radio. Their 1993 debut sold over seven million copies, and Duritz spent years dismantling the very song that made them famous, recanting "Mr. Jones" and its hunger for stardom after getting exactly what he wished for.
The mysterious French duo who hid their faces, invented the robot identity, and detonated dance music into the mainstream. Their chrome-and-gold helmets became one of pop culture's enduring enigmas. Two guys, a sampler, and a myth they refused to break.
The jam band that proved you didn't need guitar-on-guitar riffage—saxophone and violin could carry the whole load. College kids traded their live tapes like sacred relics, passing cassettes through dorm networks long before the internet caught up, and the band turned that devotion into an amphitheater-tour institution that defined summer for a generation.
Knight Rider's Michael Knight, Baywatch's Mitch Buchannon, and — no joke — the biggest thing on the German pop charts in 1989. He revived a canceled show with his own money, sang on the Berlin Wall in a light-up jacket, and then laughed at the punchline harder than anyone.
The Worm: a rebounding machine under kaleidoscope hair and a map of tattoos. Five championships, seven straight rebounding titles, a wedding dress worn to his own book signing — Rodman was the chaos engine that somehow made the Bulls dynasty run smoother.
One of the best-selling girl groups of all time and the defining R&B girl group of the late 1990s and early 2000s, famous for the powerhouse lineup of Beyoncé Knowles, Kelly Rowland, and Michelle Williams. With hits like 'Say My Name,' 'Bills, Bills, Bills,' 'Independent Women,' 'Survivor,' and 'Bootylicious,' they defined an era of confident, sexually liberated pop music while launching Beyoncé toward her eventual superstardom.
The barking Yonkers growl who crash-landed on the glossy late-90s rap charts like a dog off its chain. Earl Simmons snarled prayers over Swizz Beatz beats, made Ruff Ryders a household name, and opened a #1 movie at the box office. Equal parts menace and open wound, he was hip-hop's most ferocious voice when it needed one most.
Baltimore's harmony-stacked R&B quartet — Sisqó, Nokio, Jazz, and Woody — behind late-'90s slow jams like "In My Bed" and "Never Make a Promise." Named after the city's Druid Hill Park, they were one of the defining male R&B groups of the era, right up until Sisqó's platinum-blond "Thong Song" solo fame both lifted the group and splintered it.
Marshall Mathers from Detroit, a white rapper in a Black art form, exploded into stardom with shock-rap alter ego Slim Shady and relentless rhymes. The blond buzzcut, unapologetic controversy, Dr. Dre mentorship, and hits like 'Stan' and 'The Real Slim Shady' made him the biggest and most polarizing star in music during the early 2000s.
Before she became a name, Eva Mendes was the girl in the music videos—Aerosmith, Will Smith, Pet Shop Boys. Then she broke into film at exactly the right moment to become a defining screen presence of the 2000s multiplex.
Pete Wentz's swoopy black fringe, Patrick Stump's soaring voice, and song titles that ran on forever. "Sugar, We're Goin Down" ruled TRL and Warped Tour, making Fall Out Boy the pop-punk face of the MySpace era.
Son of the 1970s sitcom legend Freddie Prinze, who died when Freddie Jr. was a baby. He grew up carrying one of television's most poignant legacies—and then became the face of the late-90s teen-movie boom. Dimpled, kind-eyed, and impossibly likable, he was THE heartthrob of an era that believed in nice guys.
![Video thumbnail — Goo Goo Dolls – Iris [Official Music Video] [4K Remaster]](https://i.ytimg.com/vi/NdYWuo9OFAw/maxresdefault.jpg)
Buffalo bar-band punks turned the kings of the late-90s radio ballad: Johnny Rzeznik and Robby Takac spent a decade in the van before "Name" and then "Iris" made them one of the biggest acts in America — and "Iris" sat on top of the airplay chart so long it set a record that stood for over two decades.
After a decade fronting No Doubt, Gwen Stefani reinvented herself as a solo pop force in 2004 — dropping "Hollaback Girl," parading her Harajuku Girls, and launching a fashion empire. It was maximalist, brand-savvy 2000s pop at its peak.
Born into Hollywood royalty but broke through on his own terms—as the troubled daydreamer who became every indie film's favorite wunderkind. By mid-decade, he'd pivoted into blockbusters without losing the arthouse credibility, proving the 2000s' best leading men didn't have to pick a lane.
Shawn Corey Carter rose from Marcy Projects hustler to rap's defining CEO, making the 2000s the decade when hip-hop conquered the boardroom. His Imperial period—from Hard Knock Life through The Black Album and beyond—turned street rap into stadium singalongs and Grammy gold. Jay-Z didn't just make hits; he made an industry, proving rappers could own their own records and empires. The 2000s belonged to him.
The Playmate who snort-laughed at the glamour game. As MTV's Singled Out co-host she buried the pin-up script under googly faces and gross-out physical comedy — and proved a bombshell could be the funniest person in the room.
The church-family daughter from 7th Heaven who shed her wholesome image and fought her way into 2000s movie stardom. Cast at fourteen as Mary Camden, she became one of The WB's defining faces—and by her early twenties she was headlining studio films like The Texas Chainsaw Massacre and Blade: Trinity.
The third lane of the late-90s teen-pop trinity—Britney, Christina, and Jessica Simpson, marketed above all on that big Texas church-choir voice. Her debut album was a platinum hit, but her real dominance came via a reality TV show that turned her marriage into ratings gold and a Chicken of the Sea moment into the decade's defining soundbite.
Folk's answer to the underdog dream: Jewel went from a coal-heated Alaska homestead to living in a van in San Diego to 12× platinum. Her breakthrough Pieces of You rode a slow burn to the top, and by the late 90s she was unavoidable — poetry collections, platinum albums, two generation-defining radio ballads that felt permanent.
The Canadian comic who became the biggest movie star on the planet in a single calendar year. In 1994, Ace Ventura, The Mask, and Dumb and Dumber made Jim Carrey the hyperkinetic face of the decade — rubber-faced, fearless, and everywhere.
The face of the mid-90s: Randy Taylor, the wisecracking middle son on ABC's Home Improvement, whose image covered a million bedroom walls. "JTT" was the defining teen-magazine heartthrob of the decade—three initials that meant the same thing to one generation that Elvis meant to another. At the absolute peak of his fame, he walked away to go to college.
A Minnesota kid who exploded into stardom in 2001 with Pearl Harbor and Black Hawk Down, then famously stepped away. Josh Hartnett was the rare leading man who'd had enough of the machinery by 2006, turning down Superman and Batman to reclaim his life. His withdrawal was deliberate—a quiet rejection of what the moment demanded.
Born 1981, she was the teen-Shakespeare queen of the late 90s and early 2000s—flinty and wry where others were bubbly, older-souled than the wave around her. From Kat Stratford's taming to Ophelia to Desdemona to a ballerina's breakthrough, she was the thinking kid's teen-movie star.
The Kid — the backwards cap, the sweetest left-handed swing in baseball, and the Seattle Mariners star who was the face of the 90s game. Ken Griffey Jr. hit towering home runs, made highlight-reel catches, and had his name on the video games kids played and the Wheaties boxes on the breakfast table.
The curly-haired soprano saxophonist whose smooth jazz became the default soundtrack of the '90s — dentist offices, weddings, mall speakers, and hold music everywhere. Breathless (1992) is the best-selling instrumental album of all time, and he once held a single saxophone note for over 45 minutes straight.
The Eurodance duo that carried producer Frank Farian's Midas touch from Boney M. into the '90s. "Be My Lover" didn't just top charts—it scored over 6 million copies sold worldwide.
Born in 1982, LeAnn Rimes released "Blue" at thirteen in 1996 and became an overnight country sensation with an impossibly mature voice. She won Grammy Awards for Best New Artist and Best Female Country Vocal Performance in 1997, becoming the youngest person ever to win those awards. Her 1997 ballad "How Do I Live" spent a record 69 weeks on the Hot 100—Billboard later ranked it the most successful song of the 1990s.
The floppy-haired heartthrob whose face covered every bedroom wall and Tiger Beat cover after Titanic. Before he was an Oscar-winning elder statesman of film, '90s Leo was pure teen-idol "Leo-mania."
The Los Angeles radio-rock band behind "Hanging by a Moment" — a famous Billboard chart anomaly. Frontman Jason Wade's five-minute songwriting session produced a single that never hit weekly No. 1 yet finished as Billboard's No. 1 song of 2001. Earnest, huge-chorused, everywhere.
The Jacksonville metal band that defined nu-metal's MTV dominance. Fred Durst's backwards red Yankees cap and Wes Borland's shock-value body paint made them impossible to ignore. They broke through with a cover of George Michael's "Faith" reimagined as down-tuned metal. They became the sound of late-90s TRL, then evaporated just as fast.
America's freckled sweetheart of the mid-2000s — Freaky Friday, Mean Girls, a pop album, and a tabloid spotlight that never switched off. For a few years, Lindsay Lohan was the reigning teen-movie queen.
The hands-on-cheeks scream that launched a thousand parodies. As Kevin McCallister in Home Alone, Culkin became the most famous child star on Earth — and, briefly, the highest-paid kid in Hollywood.
The voice: a five-octave range and that signature whistle register that became the sound of 1990s radio dominance. Columbia executive Tommy Mottola heard her demo tape at a party in December 1988, signed her, and launched a decade-long reign that would see her become the first artist whose first five singles all reached number one, and close the 1990s with fourteen #1 hits and Billboard's Artist of the Decade award.
A shape-shifting comedy force. On Martin he played a Detroit radio DJ—and an entire neighborhood of other characters: Sheneneh, Mama Payne, Jerome, Dragonfly Jones. The show was one of Fox's highest-rated and made him a star; stand-up and movies (Bad Boys, Big Momma's House) carried the run into the 2000s.
The Bulls dynasty alpha who made basketball bigger than basketball itself. Six NBA championships in two three-peats, a Gatorade slogan that became a religion, a baseball detour ended by a two-word press release, and Air Jordans that outlasted his career by decades.
The Jamaican-accented tarot reader who ruled late-night cable — 'Call me now!' — as the face of the Psychic Readers Network. For a few years around the turn of the millennium, Miss Cleo's pay-per-minute readings were an inescapable TV-ad fixture, until the whole operation collapsed under federal scrutiny.
![Video thumbnail — My Chemical Romance - Welcome To The Black Parade [Official Music Video] [HD]](https://i.ytimg.com/vi/RRKJiM9Njr8/maxresdefault.jpg)
The eyeliner-and-marching-band emo icons behind The Black Parade. Formed in New Jersey after 9/11, MCR gave every mid-2000s teenager an anthem — "Welcome to the Black Parade," "Helena," "I'm Not Okay" — and a look.
![Video thumbnail — Ne-Yo - Miss Independent [Official Video]](https://i.ytimg.com/vi/k6M5C-oKw9k/maxresdefault.jpg)
The guy who wrote some of the biggest R&B songs of the mid-2000s before his own voice became equally unavoidable. Ne-Yo went from invisible hitmaker to chart-dominating artist in one album cycle — and never stopped being both at once.
For the first half of the 2000s, Nelly was pop-rap's biggest crossover star — the Band-Aid-cheeked St. Louis rapper behind "Hot in Herre" and "Dilemma," a run of singalong hits that owned radio, MTV, and the charts.
A classically trained dancer from Canada who became the scream queen of the '90s. Party of Five made her a household name; The Craft proved she could anchor a cult phenomenon. By Scream 3, Sidney Prescott was her definitive role—the rare horror heroine who could carry an entire franchise. In the 2000s, she stepped back to pursue her own creative vision.
Kurt Cobain, Krist Novoselic, and Dave Grohl didn't invent grunge—but their 1991 album Nevermind accidentally blew it up worldwide, displacing Michael Jackson from #1 and making flannel shirts and angst the uniform of the decade.
Gwen Stefani's bindi, bleached-blonde hair, and midriff on full display, fronting a bouncy ska-punk band out of Anaheim. "Just a Girl" and the aching "Don't Speak" made Tragic Kingdom one of the decade's defining albums.
![Video thumbnail — The Notorious B.I.G. - Juicy (Official Video) [4K]](https://i.ytimg.com/vi/_JZom_gVfuw/maxresdefault.jpg)
Brooklyn's rap king — Christopher Wallace, aka Biggie Smalls — whose effortless flow and vivid street storytelling made him the defining East Coast voice of the mid-90s. His 1997 murder, still unsolved, cut short one of hip-hop's greatest careers at just 24.
'Bye Bye Bye' and its jerky-dancing video were inescapable on TRL, announcing that five boys from Orlando could rival the Backstreet Boys. NSYNC was teen pop's other empire during the late 90s, built by the same producer and fueled by a rivalry that defined a generation.
![Video thumbnail — O.A.R. - "Shattered" [Official] Music Video](https://i.ytimg.com/vi/Qa5Mawz92xU/hqdefault.jpg)
The jam band MTV never gave a platform but college kids couldn't live without. O.A.R. — "Of A Revolution" — spread dorm to dorm on burned CDs of live shows, a band you heard about from a friend long before you ever heard them on the radio. By the time they sold out Madison Square Garden in 2006, the underground had simply become too big to ignore.
André 3000 and Big Boi met as teenagers at Lenox Square mall in Atlanta and launched one of hip-hop's most fearless acts. The South got something to say—literally—and hip-hop would never ignore it again.
Discovered on a stadium jumbotron in a beer T-shirt, she became the decade's defining pin-up via a red swimsuit and a slow-motion jog. Baywatch's C.J. Parker was less a character than a cultural symbol — and no one on Earth was more 90s-famous.
The original "famous for being famous" heiress. "That's hot," a tiny dog in her handbag, a pink Sidekick, and a permanent spot on the tabloid covers — Paris Hilton was the face of 2000s celebrity culture.
The Vermont jam band that never had a hit single and never needed one. While the radio played everyone else, Phish built an empire out of marathon two-set shows, fan-taped cassettes traded hand to hand, and festivals so big they were briefly the largest concerts in America.
![Video thumbnail — Red Hot Chili Peppers - Californication (Official Music Video) [HD UPGRADE]](https://i.ytimg.com/vi/YlUKcNNmywk/maxresdefault.jpg)
Four high-school friends from Los Angeles turned nude socks into a rock-and-roll statement, then became one of the biggest bands of the 1990s and 2000s. The Chili Peppers' sinewy funk-rock and theatrical chaos defined an era.
The teenager with a critic's favorite first kiss who grew into the 2000s' defining star. Southern charm and comic precision built through the '90s—Fear, Freeway, Election—but then Legally Blonde detonated, and she owned the decade. Walk the Line proved she could do Oscar-worthy dramatic work. Married and divorced Ryan Phillippe in a trajectory as public as her career was inescapable.
From college-radio cult band to the thinking fan's arena colossus — R.E.M. was the bridge between the 1980s underground and the 1990s alternative explosion. "Losing My Religion" and "Everybody Hurts" became anthems for a generation, and the Athens, Georgia quartet proved that you could be smart, cryptic, and absolutely massive all at once.
A teenager from Barbados who walked into a New York audition and walked out with a six-album deal, then spent the back half of the 2000s taking over pop radio. From the steel-drum bounce of 'Pon de Replay' to the umbrella-ella-ella hook that owned the summer of 2007, Robyn Rihanna Fenty went from island newcomer to global star before she turned 21.
Stand-up comic turned Hollywood golden boy whose late-80s-to-90s run defined a generation's movie shelf. From Good Morning, Vietnam (1987) through Good Will Hunting's 1998 Oscar win, Williams embodied the comedic-yet-sensitive everyman that shaped 90s cinema.
From the daytime soap to teen idol, Ryan Phillippe was the smirking heartthrob who could play both the innocent and the seducer. I Know What You Did Last Summer introduced him; Cruel Intentions cemented him as the defining rich, dangerous charmer of his moment. He married Reese Witherspoon in 1999 and became one of the era's most visible celebrity couples before their 2006 separation.
The face of the late-90s teen boom: a soap-opera Emmy winner who became Buffy the Vampire Slayer and, in a single year, also starred in two of the era's defining horror hits. For a stretch around the turn of the millennium, Sarah Michelle Gellar was the girl who could stake a vampire, outwit a masked killer, and anchor a cult-favorite TV show all at once.
An Australian pop-duo lightning strike: Savage Garden arrived in 1997 with a perfectly crafted self-titled album and didn't leave the radio for three years straight. Two studio albums, two #1 hits, 23 million copies sold — and then, in 2001, a quiet goodbye with no decline to mourn. A pop career that knew when to stop.
Canadian country-pop crossover sensation in leopard print and confidence. She sold albums by the tens of millions, and for a moment the whole world was her pickup-truck ballad audience.
"Wannabe," Girl Power, and five color-coded personas — Baby, Scary, Sporty, Ginger, and Posh — that turned a British pop group into a global phenomenon. Their faces sold everything from lunchboxes to soft drinks, and their debut became the best-selling album ever by a female group.
The Long Beach ska-punk legends who put out their early records on Skunk Records, their own DIY imprint, and whose sun-drenched sound against a backdrop of tragedy became the whole story. They broke nationally in 1995 with "Date Rape" on LA's KROQ, but the songs everyone remembers—"What I Got," "Santeria," "Wrong Way"—arrived after Bradley Nowell's heroin overdose in May 1996, two months before the album that contained them.
The funk-metal band that flipped into sunshine pop overnight with "Fly" in 1997—a reggae-tinged groove with bleak lyrics about death wrapped in an impossibly breezy hook, with Mark McGrath's frosted tips becoming the era's defining haircut. They owned the radio from 1997 to 2001—"Every Morning," "Someday," "When It's Over"—then eased into the fade, with McGrath resurfacing as a celebrity-news host on Extra.
The Denver piano-rock band whose earnest, mid-tempo anthems were the sound of mid-2000s radio and every emotional TV montage of the era. "Over My Head" broke them; "How to Save a Life," supercharged by Grey's Anatomy, made them huge.
The Orange County lifers who took punk from the underground to total radio domination in one 1994 stroke. Smash became one of the best-selling albums ever released on an independent label, with "Come Out and Play" and "Self Esteem" detonating on modern-rock radio. A second, goofier peak followed with Americana and "Pretty Fly (for a White Guy)." Decades later, frontman Dexter Holland finished a PhD in molecular biology—and the band never stopped touring.
![Video thumbnail — Third Eye Blind - Jumper (Official Music Video) [HD]](https://i.ytimg.com/vi/gRYZijLZR-Q/maxresdefault.jpg)
Stephan Jenkins' San Francisco hit machine: one self-titled 1997 debut that just would not stop producing singles — "Semi-Charmed Life," "Jumper," "How's It Going to Be," "Graduate" — all sunshine on the surface and something much darker underneath.
![Video thumbnail — Rookie of the Year (1993) Theatrical Trailer [4K] [FTD-1393]](https://i.ytimg.com/vi/gUAoirkeaVE/maxresdefault.jpg)
Las Vegas native who became the face of two defining family-movie fantasies—and then grew up into American Pie. From Rookie of the Year's 100-mph kid pitcher to King Arthur's time-traveling Calvin to Kevin in the American Pie gang, his roles bookend an entire decade of growing up.
The best-selling American girl group since the Supremes. T-Boz, Left Eye, and Chilli fused hip-hop, R&B, and a playful safe-sex message into era-defining hits — "Waterfalls," "No Scrubs," "Creep" — in baggy streetwear that a generation copied.
A Canadian comedian and prankster whose MTV show turned everyday chaos into absurdist performance art. Tom Green built a cult following by harassing his own parents on camera, hitting No. 1 on TRL with a song about putting his bum on things, and turning a testicular cancer diagnosis into a shockingly honest TV special. He was unhinged before unhinged was a brand.
Dublin's titanic arena-rock band, who peaked once in the 1980s and reinvented themselves entirely in the 1990s as ironic multimedia spectacle. The Nineties U2 was fearless—Berlin studios, video walls the size of buildings, prank calls to the White House. They nearly broke up, then wrote "One" and changed everything.
The Los Angeles band that made being a nerd sound like the coolest thing in the world. The 1994 "Blue Album" and its Spike Jonze videos — the Happy Days-themed "Buddy Holly" chief among them — turned Rivers Cuomo's sweater-clad geek-rock into a generational touchstone.
The king of musical parody, Alfred Matthew Yankovic turned accordion jokes and lyrical hijinks into a decade-long MTV empire. He made fun of the songs everyone loved—and everyone watched him do it.
Fresh from his Grammy-winning rap career, Will Smith became the biggest movie star of the '90s—charismatic, relatable, and seemingly incapable of releasing a film that didn't top the summer box office. By 1999 he was untouchable.
"Candy" arrived in 1999, when she was fifteen, in the same debut class as Britney, Christina, and Jessica Simpson. Critics sorted her into the softest lane of the four — and then she spent the early 2000s playing mean girls on screen, walked away from teen pop with an album of 70s and 80s covers, and quietly outlasted the category she'd been filed under.
Billy Corgan's Chicago four-piece: shaved head, a black ZERO shirt, and a voice that could go from a whisper to a howl inside one bar. Between Gish and Machina they were a defining act of 90s alternative rock — a #1 double album, two Grammys, and seven VMAs in a single night — and then they ended it themselves, on stage at the same Chicago club where they'd started.