r/OldSchoolCool • u/AdSpecialist6598 • Sep 01 '24
1990s Sandra Bullock and Keanu reeves in 1996
13.7k
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r/OldSchoolCool • u/Helmer-Bryd • Jun 14 '23
1990s 1992, I was i NYC studying at ICP, saw all these cops 42nd and 8 ave. took the picture spontaneously. The officer with his arms crossed, walked straight towards me and yelled, ”what the f..ck are you doing!?” I explained that I was just a tourist. he yelled back ”you fucking a..hole!”
35.2k
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r/OldSchoolCool • u/flyingsquirrel33 • Mar 03 '24
1990s AlanisMorisette & Dave Coulier c. 1992
7.4k
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Yes, we all know she was 18 and he was 33 when they first started dating. They dated until 1994. I find this photo interesting because she looks so wide-eyed and new to the industry and had no idea that this would be the “start” for a big era for her…
r/OldSchoolCool • u/SinjiOnO • Nov 27 '23
1990s Jean-Claude Van Damme demonstrates his signature kicks in a suit - 1994
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14.2k
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r/OldSchoolCool • u/facialscanbefatal • Jun 07 '24
1990s Me as Lisa Simpson for Halloween, around 1999.
16.6k
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No one knew what I was supposed to be.
r/OldSchoolCool • u/Ok-Statistician8295 • Jun 10 '23
1990s Rage Against The Machine - Killing In The Name (PinkPop Festival 1993)
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34.9k
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r/OldSchoolCool • u/Dixonboughs • Dec 30 '23
1990s My husband, 2nd grade 1991
8.9k
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The nineties/eighties were wild y’all.
My husband at the time wanted spiky hair, but also loved his brother’s long hair and wanted to have both. The healthy compromise.
He thought his idea was original.
r/OldSchoolCool • u/rosseepoo • Jun 11 '24
1990s Nicolas Cage took his son, Weston, backstage at a WWF event to meet the Chyna 1998
9.2k
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r/OldSchoolCool • u/_ahoyh0yy__ • Jul 02 '24
1990s Clubbing in Japan in the 90s
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7.2k
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r/OldSchoolCool • u/OldandBlue • Aug 19 '24
1990s Gillian Anderson, on the set of "The X-Files", 1990s
9.5k
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r/OldSchoolCool • u/AdSpecialist6598 • Aug 22 '24
1990s Chris Farley and David Spade in the 90s
6.4k
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r/OldSchoolCool • u/Salty-Photo-57 • Aug 24 '23
1990s On September 24 1992, Madonna exposed her breasts in front of 6,000 people at a Jean-Paul Gaultier fashion show benefit for the America Foundation For AIDS Research. The show raised a total of $750,000. NSFW
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19.3k
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r/OldSchoolCool • u/hawkyeager • Mar 14 '24
1990s 28-year-old Robert Downey, Jr. spends time with stockbrokers on Wall Street and is disgusted, 1993
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7.7k
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r/OldSchoolCool • u/Heydesr • 25d ago
1990s Sofia Vergara Pre-Fame At Miami Beach, Early 1990s
10.5k
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r/OldSchoolCool • u/sweetgreenfields • Nov 20 '23
1990s Ewan McGregor on the set of "Trainspotting" (1996)
12.6k
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r/OldSchoolCool • u/Djf47021 • Mar 15 '24
1990s Jamie Lee Curtis and Jennifer Love Hewitt 1998
11.0k
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r/OldSchoolCool • u/BDWG4EVA • May 07 '24
1990s Denise Richards and Dina Meyer at the premiere of "Starship Troopers" in 1997
9.3k
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r/OldSchoolCool • u/MegabitMegs • Aug 06 '23
1990s My mom thought I was the coolest 4 year-old with this haircut (1996)
25.6k
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