42 Musician & Rock Star Jokes: The 1999 “Y2K Panic, Slim Shady & The Woodstock Inferno” Edition

In 1999, the music industry was at its absolute financial peak—selling CDs like they were bottled water while a teenager named Shawn Fanning was building a “little program” called Napster that would burn the whole house down. It was the year we were convinced the world’s computers would explode at midnight, so we decided to spend our final months watching Britney Spears, Fred Durst, and a guy named Eminem fight for the soul of MTV.

The 1999 Soundboard Top 10: “The Slim Shady LP, Latin Explosion & The End of the World”

The Eminem “The Slim Shady LP” Arrival: Why was everyone’s mom angry? Because a blonde guy from Detroit showed up to prove that you could be the funniest, scariest, and most lyrical person in music while offending 90% of the population.
The Britney vs. Christina Rivalry: Why the pigtails vs. the voice? Because 1999 was the year you had to choose a side: were you Team Britney’s “…Baby One More Time” or Team Christina’s “Genie in a Bottle”? There was no middle ground.
The Woodstock ’99 Disaster: Why the fire? Because if you put a million angry kids in the heat with expensive water and Fred Durst screaming “Break Stuff,” you don’t get peace and love—you get a riot and a very stressed-out Sheryl Crow.
The Ricky Martin “Livin’ la Vida Loca” Fever: Why the leather pants? For the “Latin Explosion” that proved the entire world was ready to shake their hips to a brass section and a song about a woman who drinks blue champagne.
The Red Hot Chili Peppers “Californication” Rebirth: Why the video game? Because John Frusciante returned, the band put their shirts back on (mostly), and they created the ultimate soundtrack for driving toward a sunset.
The Backstreet Boys “Millennium” Mania: Why the white suits? Because they sold 1.1 million copies in a single week, proving that five guys harmonizing about wanting it “that way” was more powerful than the fear of the Y2K bug.
The Dr. Dre “2001” Masterpiece: Why the delay? Because Dre took seven years to perfect a snare drum sound, but when it finally dropped, it reminded everyone that the West Coast still owned the streets.
The Santana “Supernatural” Comeback: Why the hats? For a guy who had been a legend since the 60s suddenly becoming the biggest star of 1999 because he paired a guitar solo with Rob Thomas.
The Kid Rock “Devil Without a Cause” Boom: Why the fur coat? For the year we all pretended that mixing country, rap, and heavy metal while having a pimp-style hype man was a perfectly normal musical choice.
The Prince “1999” Obsession: Why the old song? Because everyone spent the entire year playing a track from 1982 because it was finally, legally, and mathematically relevant.

The Full 1999 Musician & Rock Star Archive

The Moby “Play” Takeover: Why every commercial? For an album that was so popular every single song on it was licensed for a movie, car ad, or coffee shop.
The Rage Against The Machine “The Battle of Los Angeles”: Why the protest? Because Zack de la Rocha reminded us that even in the middle of a pop boom, the system was still a “Guerrilla Radio” station.
The Lou Bega “Mambo No. 5” Mystery: Why all the names? For a song that taught every man in 1999 a list of women’s names he would never actually meet.
The Smash Mouth “All Star” Eternal Loop: Why the Shrek vibes? For the song that became so infectious it is still playing in the background of every supermarket on Earth today.
The Macy Gray “I Try” Rasp: Why the voice? For proving that sounding like you just swallowed a bag of gravel could actually be the most soulful thing on the radio.
The Foo Fighters “There Is Nothing Left to Lose”: Why the “Learn to Fly” video? For Dave Grohl dressing up as a flight attendant and proving he was the funniest man in rock.
The TLC “FanMail” Return: Why “No Scrubs”? For the anthem that taught an entire generation of men that sitting in the passenger side of their best friend’s ride was a social death sentence.
The Muse “Showbiz” Debut: Why the high notes? For the year Matt Bellamy decided he wanted to sound like Radiohead but with more space lasers.
The Destiny’s Child “The Writing’s on the Wall”: Why the rules? For the album that introduced us to Beyoncé’s world-domination plan and taught us how to say “Say My Name.”
The Limp Bizkit “Significant Other”: Why the red cap? For the moment Fred Durst became the most hated and loved man in America by doing it all for the “Nookie.”
The Sigur Rós “Ágætis byrjun”: Why the alien language? For an Icelandic band that proved you didn’t even need to speak a real language to make people cry.
The blink-182 “Enema of the State”: Why the running naked? For the album that made pop-punk the official religion of every 13-year-old with a skateboard.
The Silverchair “Neon Ballroom”: Why the orchestra? For the teenage Australians who grew up, got depressed, and decided to add 40 violins to their grunge riffs.
The Jennifer Lopez “On the 6” Debut: Why the subway? For the moment J.Lo proved she wasn’t just an actress, she was a one-woman industry with a global dance hit.
The Nine Inch Nails “The Fragile”: Why two discs? Because Trent Reznor needed three hours of industrial noise and piano to explain exactly how sad he was.
The Vengaboys “We’re Going to Ibiza”: Why the bus? For the year European dance music decided to be as colorful and annoying as possible, and we all loved it.
The Korn “Issues” Doll: Why the velvet? For the year Jonathan Davis decided that puppets were the only thing that truly understood his pain.
The Shania Twain “Man! I Feel Like a Woman!” (Peak): Why the top hat? For the year Shania officially finished her mission to turn every human being on Earth into a country music fan.
The Slipknot Self-Titled Debut: Why the jumpsuits? For the nine guys from Iowa who showed up to remind us that heavy metal should involve masks, screaming, and hitting beer kegs with baseball bats.
The Sugar Ray “Every Morning”: Why the halo? For the band that forgot they were a metal band and decided to just write perfect songs for drinking lemonade on a porch.
The Jay-Z vs. Nas (The Warm-up): Why the tension? For the year the throne was up for grabs and everyone was waiting for the first punch to be thrown.
The Creed “Human Clay”: Why the arms wide open? For the band that proved you could sell 11 million albums by sounding exactly like a very dramatic church service.
The Chemical Brothers “Surrender”: Why the “Hey Boy Hey Girl”? For the duo that kept the rave alive while everyone else was busy listening to boy bands.
The Fiona Apple “When the Pawn…”: Why the long title? For an album title so long it took up the entire space on the back of the CD case.
The Eiffel 65 “Blue (Da Ba Dee)”: Why the aliens? For a song so simple and blue that it managed to get stuck in the collective brain of humanity for eternity.
The Stereophonics “Performance and Cocktails”: Why the raspy vocals? For the Welsh band that proved you could rule the UK charts just by singing about bartending and small towns.
The Pet Shop Boys “Nightlife”: Why the wigs? For the duo that entered the new millennium looking like orange-haired cyber-punks from a very polite future.
The Death of Curtis Mayfield: Why the soul loss? For the passing of a legend who taught us about “People Get Ready” just as the world prepared for a digital reset.
The Napster Launch: Why the lawsuits? For the cat icon that made Lars Ulrich very angry and changed the value of a song from $18.99 to $0.00.
The Total Request Live (TRL) Peak: Why Carson Daly? For the man who held the keys to the kingdom, deciding which video would be #1 based on thousands of screaming teenagers in Times Square.
The Lenny Kravitz “American Woman”: Why the aviators? For the year Lenny proved he could cover a classic and make it sound exactly like it was still 1969.
The 1999 Final Music Vibe: Why did the year feel like a countdown? Because of the silver puffer jackets, the digital glitches in every music video, and the collective fear that when the clock struck twelve, our Discmans would stop working and we’d have to actually talk to each other.