Woodstock '99
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6correct to beat the crowd
50 free Woodstock '99 trivia questions with answers — music quiz, new questions added Oct 2026.
Woodstock '99 was meant to mark three decades since the most famous music festival of all. Instead it is remembered for brutal heat, overpriced water, an angry crowd and a final night that ended in flames. This quiz follows the lineup across the whole weekend: who opened each day, who closed the two main stages, which acts dropped out before the gates opened, and which sets became infamous. It also covers the site, the organizers, the television coverage and the documentaries that revisited it all years later. It is written for anyone who watched it unfold at the time, anyone who discovered it through a documentary, and anyone who simply loves late-nineties music. Every answer comes with a short explanation.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which punk band bashed dummies of the Backstreet Boys with a plastic bat during a Friday set at Woodstock '99?
The Offspring
The Offspring lined up five dummies wearing the boy band's faces, and the crowd joined in by pelting them with plastic bottles.
Q 02What did activists hand out at Woodstock '99 on Sunday that fans then used to start bonfires?
Candles
Candles came from an anti-gun-violence group called PAX, whose vigil plan had never been cleared with local firefighters.
Q 03Which rap act kicked beach balls with $100 bills taped to them into the Woodstock '99 crowd to protest high prices?
Insane Clown Posse
Insane Clown Posse watched fans scrap over the cash, and a year later the duo launched a festival of their own, the Gathering of the Juggalos.
Q 04What kind of site hosted Woodstock '99, chosen partly because promoters thought a wall could keep gate-crashers out?
A former Air Force base
A former Air Force base, Griffiss had shut in 1995, and its vast stretches of shadeless concrete and asphalt trapped the heat day and night.
Q 05Which band's Saturday set at Woodstock '99 is widely blamed for sparking violence as fans tore plywood from the walls?
Limp Bizkit
Limp Bizkit were asked mid-set to calm the crowd, but their frontman told fans not to mellow out and later crowd-surfed on a torn-off panel.
Q 06Which animated sitcom spoofed Woodstock '99 with a character whose clothes catch fire as he balks at $8 bottled water?
The Simpsons
The Simpsons sent bus driver Otto to the festival, where the woman who douses the flames with her own bottle ends up as his fiancée.
Q 07Which festival was announced within a week of Woodstock '99, then gave fans free parking and a free bottle of water?
Coachella
Coachella debuted in Indio, California, that October, and its well-behaved crowd stood in stark contrast to the violence of three months earlier.
Q 08Which band played the closing set of Woodstock '99 on Sunday night while bonfires spread across the crowd?
Red Hot Chili Peppers
Red Hot Chili Peppers were begged by the city's mayor to go back on stage and calm the crowd; some outlets later blamed their choice of cover song for stoking the blazes.
Q 09Rumors of a secret superstar finale at Woodstock '99 ended with footage of which late star of the 1969 festival?
Jimi Hendrix
Jimi Hendrix appeared only on screen beside a laser show, and fans who had heard whispers of Prince or the Rolling Stones booed and turned on the vendor booths.
Q 10Which upstate New York city hosted Woodstock '99, with a mayor who hoped the festival would revitalize the area?
Rome
Rome's mayor announced the festival alongside Hillary Clinton, and on the final night he pleaded with the closing band to go back out and calm the crowd.
Q 11Which band headlined Saturday night at Woodstock '99, one of only five acts that had also played Woodstock '94?
Metallica
Metallica followed Rage Against the Machine to close the East Stage, five years after sharing the 1994 bill with Aerosmith and Nine Inch Nails.
Q 12Which nu metal band's Friday night set at Woodstock '99 left its singer needing oxygen and an IV for heat exhaustion?
Korn
Korn frontman Jonathan Davis said the crowd moved like an immense wave of sound rolling for miles, and the next act's singer dreaded following such a ferocious set.
Q 13Which performer, later named a breakout star of Woodstock '99, urged fans to throw their empty water bottles onstage?
Kid Rock
Q 21Which Rage Against the Machine member set fire to an American flag on stage at Woodstock '99?
Tim Commerford
Tim Commerford, the band's bassist, lit the flag while the group played Killing in the Name; guitarist Tom Morello later defended the crowd in the New York Times.
Q 22Which British DJ's late-night rave set at Woodstock '99 was cut short after a stolen truck drove into the crowd?
Fatboy Slim
Fatboy Slim and his entourage were told to get out at once; they fled to a nearby airport and flew out the next morning.
Q 23Which band was joined at Woodstock '99 by Doors guitarist Robby Krieger for a cover of Roadhouse Blues?
Creed
Creed brought Krieger out as a surprise on Sunday, three decades after the Doors had turned down an offer to play the original festival.
Kid Rock made the request between songs out of disgust at concession prices; fans waiting for him had earlier pelted the day's opening band.
Q 14Which singer's Saturday set at Woodstock '99 drew boos and chants from fans impatient for the next band?
Alanis Morissette
Alanis Morissette heard fans chanting the next band's name near the end of her set, and that band's singer then mocked her on stage for mellowing the crowd.
Q 15Which singer called her Friday set at Woodstock '99 the worst gig of her career after being heckled and pelted?
Sheryl Crow
Sheryl Crow said she nearly ended the set early in disgust, and she spent years criticizing the festival for the way its crowd behaved.
Q 16Which rapper, introduced at Woodstock '99 by actress Rosie Perez, won praise for his Friday set?
DMX
DMX was among the acts whose performances impressed critics before coverage of the weekend turned to the chaos around them.
Q 17Which soul legend led off Friday's East Stage bill at Woodstock '99, hours before the nu metal and punk acts?
James Brown
James Brown, the Godfather of Soul, shared Friday's main bill with Jamiroquai and Live before the day turned much heavier.
Q 18Which country legend played first on the East Stage on Sunday at Woodstock '99, long before the night's riots?
Willie Nelson
Willie Nelson shared Sunday's main bill with Elvis Costello and a swing orchestra, a gentle start to the weekend's most destructive day.
Q 19Woodstock '99 took place in which month, a few weeks short of the original festival's thirtieth anniversary?
July
July 22 to 25 brought temperatures above 100°F to the shadeless site, while the 1969 original had been held in the middle of August.
Q 20Which TV network covered Woodstock '99 extensively, then evacuated its whole crew amid Sunday night's violence?
MTV
MTV staff were pelted with bottles and batteries, and veteran anchor Kurt Loder likened the final night to reporting from a war zone.
Q 24Which British band closed Friday's East Stage at Woodstock '99, its frontman nervous about following a ferocious set?
Bush
Bush went on without incident and even calmed the crowd a little, three months before the band released the album The Science of Things.
Q 25Which thrash metal band closed the West Stage at Woodstock '99 on Sunday after a tribute to its late ex-drummer?
Megadeth
Megadeth dedicated a song to Gar Samuelson, who had died eleven days earlier, and a fan's laser pointer prompted frontman Dave Mustaine to scold the crowd mid-set.
Q 26Which Canadian band opened Saturday's East Stage at Woodstock '99 and was pelted with bottles by impatient fans?
The Tragically Hip
The Tragically Hip singer Gord Downie answered by singing O Canada for the many flag-waving Canadians present, only for others to boo and strike up the US anthem.
Q 27Which N.W.A alumnus played the West Stage at Woodstock '99 on Saturday and joked about cutting his set short?
Ice Cube
Ice Cube walked back on after two minutes; he had flown in from Southern California on a rented Boeing 737 shared with two nu metal bands.
Q 28Which Austin Powers actor walked on stage at Woodstock '99 to introduce one of Saturday night's biggest bands?
Verne Troyer
Verne Troyer, the films' Mini-Me, warned the crowd they were about to get the worst, and stars including Jennifer Aniston watched the set that followed.
Q 29Which song from Saturday's most notorious set at Woodstock '99 later named a podcast about the weekend?
Break Stuff
Break Stuff was the point at which crew in the sound tower were ordered to abandon their post, and The Ringer borrowed its title for an eight-part series.
Q 30Which bassist walked on stage naked for his band's Sunday night set at Woodstock '99?
Flea
Flea also spoke up from the stage against the groping of women in the crowd, and he played naked again at Reading and Leeds that year.