Left: Two women in fitted blue dresses and a man in a suit pose together and smile. Right: A woman holds a mustard bottle over her head while holding a pretzel with mustard, looking up playfully.

The last years of the 20th century were a remarkable time of profound, rapid change, made up of truly unforgettable moments. Between 1977 and 1999, the world itself was caught right in between nostalgia and excitement for the future. From iconic fashion and music to moments that shaped history, this collection of images tells the story of a world on the edge of a new millennium.

1. On December 10, 1997, Julia Hill climbed a 1500-year-old redwood tree that was named Luna and she didn’t come down for another 738 days

A person wearing a red outfit sits high in the branches of a tall pine tree on a mountainside, overlooking a vast forested landscape and distant buildings.
gregornot/via reddit.com

2. Opening up Starfox 64 for Christmas in 1997

A young boy wearing glasses sits on the floor opening a boxed toy, surrounded by gift bags and other children. Adults sit on a couch nearby, and snacks are scattered around the cozy living room.
educatedignorance/via reddit.com

3. A summer in Paris, 1997

People relax on a grassy slope near fountains by the Eiffel Tower in Paris. Some children play in the water, and others lounge on the grass under a clear sky, with the iconic tower in the background.
tirepointunderscore/via reddit.com

4. Prince meeting Muhammad Ali, 1997

A man in a green suit sits smiling while another man in a yellow polo shirt gently pats his head. They are seated indoors in a decorated room with framed art and a china cabinet in the background.
amazingsandwiches/via reddit.com

5. Getting ready to head to the skate park, 1997

A group of teenagers sit and stand on a grassy slope outside a house, some talking and others looking around. Two guys with skateboards and backpacks stand in the foreground. The mood appears casual and social.
all_you_people/via reddit.com

6. Jim Carrey and Chris Farley, 1997

Two men standing outdoors, smiling for the camera. The man on the left wears a blue dress shirt and tie, while the man on the right wears a black T-shirt with a martial arts logo and has his arm around the other man.
djf47021/via reddit.com

7. Michael Jordan’s food poisoning game, 1997

Two Chicago Bulls basketball players in red uniforms hug and support each other on the court, surrounded by a cheering crowd. A TV camera films them up close.
seraphenigma/via reddit.com

8. Fran Drescher, Peter Bergman, and Pam Anderson, 1997

Three people pose in front of a gray textured backdrop: a man in a suit and tie stands between two women wearing matching light blue sleeveless dresses with deep necklines, all smiling at the camera.
bruinsrock11/VIA reddit.com

9. Pope Francis on public transit in Buenos Aires, 1998

Black and white photo of people sitting and standing in a crowded subway car. The central figure, an older man in a dark coat, looks directly at the camera amid other passengers, some talking and others looking away.
userdeleted/via reddit.com

10. New Yorkers gathering to watch the Seinfeld finale in Times Square, 1998

A crowd stands on a busy street at night, watching a large Panasonic screen above showing a movie scene with subtitles. Neon signs and storefronts, including U.S. Marine Corps and theater marquees, light up the area.
sirtimaey/via reddit.com

11. Brittany Murphy, 1998

A woman outdoors holds a mustard bottle on her head with one hand and a pretzel topped with mustard and a napkin in the other, looking upward with a playful expression.
userdeleted/via reddit.com

12. Vacation at the Tower of Pisa, 1998

A young girl poses in front of the Leaning Tower of Pisa, appearing to hold up the tilted tower with her hand. The sky is overcast, and buildings and grass are visible in the background. The date "4 15 '98" is stamped on the image.
rationalluchadore/via reddit.com

13. Tara Reid in her American Pie screen test, 1998

A young woman with long blonde hair styled in two low pigtails, wearing a light purple top and smiling against a plain dark background.
dmo12291986/via reddit.com

14. Matt Damon, Ben Affleck, and Robin Williams accepting their Oscars in 1998

Three men in tuxedos are posing together, each holding an Oscar trophy, in front of an Oscar-themed backdrop at an awards ceremony.
amonalili12/via reddit.com

15. Robin Williams under the Golden Gate Bridge, 1998

A man in a hat and leather jacket leans casually against a chain fence near the Golden Gate Bridge, with the bridge’s structure visible overhead and water in the background. The photo is in black and white.
shortsleaves/via reddit.com

16. The cast of Seinfeld after shooting their final scene, 1998

Four people share a group hug in a living room set, with one person standing aside in the background. The image is in black and white and has a warm, nostalgic atmosphere.
poohbizzle79/via reddit.com

17. Richard Proenneke, the man who lived alone in the Alaskan wilderness for nearly 30 years, 1998

A person in winter clothing stands in the doorway of a small rustic log cabin surrounded by snow and trees. Various tools, pots, and supplies hang on the cabin's exterior. Snow covers the roof and ground.
userdeleted/via reddit.com

18. The classic 1999 desk setup

A man with sunglasses sits at a wooden desk with an old CRT monitor and keyboard. The desk is cluttered with computer accessories, books, and hats. A Marilyn Manson poster hangs on the blue wall behind him.
userdeleted/via reddit.com

19. Getting ready for the new century, New Years, 1999

A group of young adults at a lively indoor party, some holding drinks. One person in the center wears a "SECURITY" shirt and waves, while colorful posters and smiling faces fill the busy, cheerful scene.
i8suspiciouscheese/via reddit.com

20. Kevin Bacon on the set of Hollow Man celebrating his son’s 10th birthday, 1999

Two children pose with a chocolate birthday cake inside a cozy room. An adult in a bald mask and blue outfit stands behind them. Another person is in the background, partially out of focus.
jalbert63/via reddit.com

21. Playing StarCraft in 1999

A young boy with short blond hair sits at a desk using an old desktop computer with a CRT monitor. He looks back over his shoulder toward the camera. The room has wood paneling and various desk items.
goldfynch/via reddit.com

22. Who remembers LAN parties?

Hundreds of people, many shirtless, sit closely together at old computer stations in a large, crowded room, with dim lighting and monitors illuminating the scene.
lifeandtimes89/via reddit.com

23. Keanu Reeves and Carrie Anne Moss celebrating the release of The Matrix, 1999

A man in a dark suit leans his head on the shoulder of a smiling woman in a sleeveless top. They are holding hands and standing close together in a softly lit room. The photo is in black and white.
hikensnorkel/via reddit.com

24. Scarlett Johansson, surrounded by Destiny’s Child, 1999

Five young women pose together. Four wear matching Tommy Hilfiger outfits with crop tops and overalls, while one in the center wears a red long-sleeve shirt and jeans. They all smile at the camera in a backstage setting.
userdeleted/via reddit.com

25. New Years Eve, in New York, 1999

A large crowd gathers in Times Square at night, surrounded by bright lights, tall buildings, and billboards, including a prominent “ABCNE” sign. Many people wear winter clothing. The scene is lively and festive.
via wikimedia commons

Want to see more late-1900s content?

Check out 19 Photos of Famous Actresses from the 1960s-1980s, or take a look at 20 Mugshots from the Electric 1980s. Finally, if you want to see some unexpected stories about actors from the late ’90s, check out 15 Unexpected Stories About Actors from the 1970s-1990s.

Meet the Writer

Patrick is a writer based in upstate New York, where he grew up and still calls home. Over the past year, he’s been diving deep into storytelling, especially tales rooted in history, the Wild West, lost treasures, and ancient artifacts. He’s also drawn to unsolved mysteries and whatever the internet can’t stop talking about.

Whether it’s a centuries-old legend or a bizarre internet rabbit hole, Patrick is always chasing the threads of a compelling story. When he’s not chasing stories, Pat’s probably hiking mountain trails with his dog, exploring new corners of the U.S., or doom-scrolling between hangouts with friends and family. He finds inspiration in nature, forgotten places, and random conversations—anything that sparks curiosity. Whether it’s city streets or backcountry paths, Patrick’s always on the lookout for the next great story.