The year 1999 doesn’t seem so distant — until you see the photos and realize it was nearly 30 years ago. Standing on the edge of a new millennium, it was the year of flip phones, frosted tips, and one last hoorah before things went digital. “The Matrix” hit theaters, Y2K panic was in full swing (remember when people thought their computers would combust?), and all the kids were obsessing over their AOL screen names. These vintage snapshots capture all the highs and lows of a year suspended between decades.
Contents
1. ‘Partying Like It’s 1999, in 1999’2. Madonna Poses for a Snap at the 41st Grammy Awards in Los Angeles3. You Can Almost Hear the Dial-Up Internet if You Look Closely Enough4. ‘Natalie Portman in High School, 1999.’ So Her Face Card Has Always Been Flawless, Got It5. Russian President Boris Yeltsin Waves Goodbye From the Kremlin as Vladimir Putin Comes Into Power, December 19996. Jennifer Coolidge at an Awards Show8. Smoke Rises After a NATO Airstrike During the Kosovo Conflict in Belgrade, Yugoslavia9. The Many Faces of Buffy: Sarah Michelle Gellar Being Goofy During the Filming of ‘Buffy the Vampire Slayer’10. A Y2K Handbook on How To Survive a Digital Doomsday11. Christian Bale and Director Mary Harron Behind the Scenes of ‘American Psycho’12. Keanu Reeves and Co-Star Carrie-Anne Moss Pose for a Snap During an Event for ‘The Matrix’13. A Young Amy Winehouse Looking Radiant14. A Prop Actor Behind the Scenes of ‘Star Wars: Episode I – The Phantom Menace’15. … and Here’s a Stunt Double Taking Flight During the Epic Fight Scene Between Han Solo and Darth Maul16. Matthew McConaughey’s Mugshot After Being Arrested in Texas for ‘Disturbing the Peace’ and Playing the Bongos Naked17. ‘British Raver Girls Partying in Ibiza, 1999’18. Napster Launched in June, 1999, Forever Changing the Way We Download and Listen to Music19. … and the Face We All Made After Accidentally Downloading a Million Viruses on the Home PC From Napster20. ‘Shania Twain at the 41st Grammy Awards, 1999’21. ‘1999 Was a Good Year for Frosted Tips.’ Yes, Yes It Was22. Carmen Elektra and Fred Durst of Limp Bizkit at an MTV Party23. Angelina Jolie and Brother James Haven at the 1999 Golden Globe Awards24. Tim Burton, Christina Ricci, Johnny Depp, and Casper Van Dien at the Premiere of ‘Sleepy Hollow’ in Los Angeles25. ‘Nell McAndrew as Lara Croft at the International Toy Fair, 1999’26. Droves of People Partying at Woodstock ’99 Before Chaos Ensued27. A State Trooper Surveys the Wreckage From Woodstock ’9928. Ozzy Osbourne Rocking His Signature Dark Blue Shades29. ‘Brad Pitt and Jennifer Aniston in Granada, Spain’30. Adrien Brody and John Leguizamo on the set of ‘Summer of Sam’31. ‘Pamela Anderson Draped in a Canadian Flag, 1999’Searching for more stories from the ’90s?
1. ‘Partying Like It’s 1999, in 1999’
2. Madonna Poses for a Snap at the 41st Grammy Awards in Los Angeles
3. You Can Almost Hear the Dial-Up Internet if You Look Closely Enough
4. ‘Natalie Portman in High School, 1999.’ So Her Face Card Has Always Been Flawless, Got It
5. Russian President Boris Yeltsin Waves Goodbye From the Kremlin as Vladimir Putin Comes Into Power, December 1999
6. Jennifer Coolidge at an Awards Show
8. Smoke Rises After a NATO Airstrike During the Kosovo Conflict in Belgrade, Yugoslavia
9. The Many Faces of Buffy: Sarah Michelle Gellar Being Goofy During the Filming of ‘Buffy the Vampire Slayer’
10. A Y2K Handbook on How To Survive a Digital Doomsday
11. Christian Bale and Director Mary Harron Behind the Scenes of ‘American Psycho’
12. Keanu Reeves and Co-Star Carrie-Anne Moss Pose for a Snap During an Event for ‘The Matrix’
13. A Young Amy Winehouse Looking Radiant
14. A Prop Actor Behind the Scenes of ‘Star Wars: Episode I – The Phantom Menace’
15. … and Here’s a Stunt Double Taking Flight During the Epic Fight Scene Between Han Solo and Darth Maul
16. Matthew McConaughey’s Mugshot After Being Arrested in Texas for ‘Disturbing the Peace’ and Playing the Bongos Naked
17. ‘British Raver Girls Partying in Ibiza, 1999’
18. Napster Launched in June, 1999, Forever Changing the Way We Download and Listen to Music
19. … and the Face We All Made After Accidentally Downloading a Million Viruses on the Home PC From Napster
20. ‘Shania Twain at the 41st Grammy Awards, 1999’
21. ‘1999 Was a Good Year for Frosted Tips.’ Yes, Yes It Was
22. Carmen Elektra and Fred Durst of Limp Bizkit at an MTV Party
23. Angelina Jolie and Brother James Haven at the 1999 Golden Globe Awards
24. Tim Burton, Christina Ricci, Johnny Depp, and Casper Van Dien at the Premiere of ‘Sleepy Hollow’ in Los Angeles
25. ‘Nell McAndrew as Lara Croft at the International Toy Fair, 1999’
26. Droves of People Partying at Woodstock ’99 Before Chaos Ensued
27. A State Trooper Surveys the Wreckage From Woodstock ’99
28. Ozzy Osbourne Rocking His Signature Dark Blue Shades
29. ‘Brad Pitt and Jennifer Aniston in Granada, Spain’
30. Adrien Brody and John Leguizamo on the set of ‘Summer of Sam’
31. ‘Pamela Anderson Draped in a Canadian Flag, 1999’
Searching for more stories from the ’90s?
Read 29 Retro Photos That Will Transport You Straight Back to 1991 for a glimpse of what was happening at the start of the decade, or check out 17 Real-Life ’90s High School Photos That Feel Like a Teen Movie for some more nostalgia. If you’re a big collector, take a look at 10 Toys From the ’90s That Are More Valuable Today.
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