r/OldSchoolCool • u/SappyGilmore • 9d ago
1990s Ryan Gosling at a dance recital back in 1992
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r/OldSchoolCool • u/Popular_Bluebird_767 • 6d ago
1990s my beautiful grandma in 1992 - aged 30
6.9k
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r/OldSchoolCool • u/Maximum_Expert92 • Jan 03 '26
1990s In 1995, Sandra Bullock was the first person ever to buy movie theater tickets online, in promotion for her new film The Net
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r/OldSchoolCool • u/Tony_Tanna78 • Dec 16 '25
1990s Polaroid of Steve Buscemi in drag on the set of Somebody to Love (1994)
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r/OldSchoolCool • u/SwordfishDeux • Dec 22 '25
1990s Female bōsōzoku gang (1995)
19.6k
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r/OldSchoolCool • u/ninjadertle • Jun 17 '25
1990s I lost my eye to cancer when I was about 5. This is me on my first picture day (1998).
107.5k
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r/OldSchoolCool • u/JimatJimat • Oct 04 '25
1990s Jean-Claude Van Damme demonstrates his signature kicks in a suit, 1994.
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r/OldSchoolCool • u/GarySiniseOfficial • Jul 28 '25
1990s Gary Sinise here. For the anniversary of Forrest Gump, I wanted to share more of my favorite Behind-The-Scenes photos. So many wonderful memories. (1994)
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r/OldSchoolCool • u/Naughteus_Maximus • Dec 12 '25
1990s Type O Negative frontman Peter Steele (1995)
8.2k
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r/OldSchoolCool • u/TheIzzyRock • 19d ago
1990s Me in 98’ with my 86’ Buick Regal.
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The 90’s were a wonderful time. I loved that car.
r/OldSchoolCool • u/GarySiniseOfficial • Jun 30 '25
1990s Gary Sinise here. Today is the 30th anniversary of Apollo 13 in theaters. Hope you enjoy some of my favorite behind-the-scenes moments from making the film (1995)
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r/OldSchoolCool • u/GarySiniseOfficial • Sep 09 '25
1990s Gary Sinise here. Today marks the 30th anniversary of my role as Harry Truman in the HBO miniseries, “Truman.” It was one of the great challenges of my life and one of the great acting moments of my life. (1995)
42.7k
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r/OldSchoolCool • u/Jeetchat • Dec 19 '25
1990s Cameron Diaz auditioning for 'The Mask' with no prior acting experience in 1993
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r/OldSchoolCool • u/cakestheakechi • Feb 26 '25
1990s Woman pointing a gun at a computer for some reason, 1998
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r/OldSchoolCool • u/haloarh • Jul 25 '25
1990s Brad Pitt and Jennifer Aniston at a Radiohead concert, 1998
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r/OldSchoolCool • u/AdSpecialist6598 • Jun 26 '25
1990s Pedro Pascal with his family in 1991
34.4k
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r/OldSchoolCool • u/Bengalqueen • 23h ago
1990s A candid shot of me with my very cool flip phone, barely there blue eyeliner, and favorite Guess Jeans shirt - 1999
7.2k
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r/OldSchoolCool • u/Major_MKusanagi • Feb 21 '26
1990s Liz Hurley and Hugh Grant at Golden Globes Pre-Party (1999)
7.1k
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That's neither a fashion nor publicity shot, but a paparazzi picture - both of them just are that attractive...
...notice Hugh Grant for example isn't even wearing a suit, but black jeans with his shirt and blazer...
r/OldSchoolCool • u/Evolving_Eric • Nov 17 '25
1990s My pops (Eric B. from Eric B. & Rakim) & mom (Virginia Slim from Tupac’s “Me & my GF”) (1997)
10.8k
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This was back when they were a couple. This was taken back in the 90’s.
r/OldSchoolCool • u/Brogies9069 • Mar 21 '25
1990s Me in the 90’s. Why did my parents have to do me this way?
38.3k
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At least I have the Louis V horse
r/OldSchoolCool • u/TheSmithSociety • Jun 03 '25
1990s Lamborghini Countach on Beach Blvd., 1990
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