25 Vintage Photos From 1999 Patrick Nichols September 9, 2025 at 9:33 AM 2 Five young women pose together; four wear matching Tommy Hilfiger outfits with crop tops and sporty pants, and the fifth, in the center, wears denim overalls over a red shirt. They are smiling in a backstage setting.
- - 25 Vintage Photos From 1999
Patrick Nichols September 9, 2025 at 9:33 AM
2
Five young women pose together; four wear matching Tommy Hilfiger outfits with crop tops and sporty pants, and the fifth, in the center, wears denim overalls over a red shirt. They are smiling in a backstage setting.
Last on September 9, 2025 by Matt Staff
This collection of 25 photos is able to provide a powerful glimpse into the time period that was the late '90s. It was a time when you either had to wait around for your film to be properly developed, when the internet made all the weird noises, and when trends moved more slowly. Let's dive now into 25 vintage photos that will show you 1999 like you've never seen it before. Enjoy the trip.
1. If you grew up in the '90s, this looks awfully familiar
somekindofspy/via reddit.com2. Seth MacFarlane in 1999
jimathimat/via reddit.com3. Keanu Reeves and Carrie-Anne Moss chatting between takes on The Matrix
kkan2020/via reddit.com4. Partying at a rave in Ibiza, 1999
voodoomac11/via reddit.com5. Pamela Anderson sporting the Canadian flag, 1999
nomadsound/via reddit.com6. Matthew McConaughey's mugshot from 1999
macpesce/via reddit.com7. Heath Ledger's Polaroid selfie with Larisa Oleynik, Joseph Gordon-Levitt, and Julia Stiles on the set of 10 Things I Hate About You, 1999
kylan910/via reddit.com8. Julia Butterfly Hill, the environmentalist who lived in a 200-foot tree for 738 days
comprehensive-way482/via reddit.com9. Natalie Portman in high school, 1999
userdeleted/via reddit.com10. Sigourney Weaver with Alan Rickman, 1999
istraman/via reddit.com11. Nicole Kidman and Tom Cruise at the premiere of Eyes Wide Shut, 1999
spcialconcern1700/via reddit.com12. Kevin Bacon on the set of Hollow Man, celebrating his son's 10th birthday
jalbert653/via reddit.com13. Reese Witherspoon and Tara Reid at a Cruel Intentions event, 1999
userdeleted/via reddit.com14. Christian Bale and director Mary Harron between takes during American Psycho, 1999
noahyhang/via reddit.com15. Penelope Cruz and Salma Hayek at the premiere of Dogma, 1999
jfoughe/via reddit.com16. Angelina Jolie, Brittany Murphy, and Winona Ryder at the premiere of Girl, Interrupted, in 1999
chris-burke/via reddit.com17. A massive LAN party in Stockholm, Sweden, 1999
lifeandtimes89/via reddit.com18. Rose Byrne goofing around with Heath Ledger, 1999
_captain_holt_/via reddit.com19. Scarlett Johansson surrounded by Destiny's Child, 1999
userdeleted/vias reddit.com20. Britney Spears and Melissa Joan Hart on the set of the Crazy music video, 1999
userdeleted/via reddit.com21. Christine Aguilera promoting her first album, 1999
emeraldnob/via reddit.com22. Mariah Carey, walking the streets of Manhattan, 1999
vilvetvika/via reddit.com23. Brad Pitt, on the set of Snatch, 1999
jimlahey2100/via reddit.com24. Jennifer Lopez at her surprise birthday party in New York, 1999
crowitz/via reddit.com25. Daft Punk, before they started wearing helmets, DJing in Florida, 1999
chris-burke/via reddit.comWant to see more content from the '90s?
Check out 20 Celebrity Yearbook Photos From The 1990s, or take a look at 20 Vintage Photos That Capture Adulthood in the 1990s. Finally, if you want to see the coolest cars from the '90s, take a look at 20 of the Coolest Cars From the 1990s.
Source: "AOL Lifestyle"
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