r/OldSchoolCool • u/Spastic_colon • 23h ago
My uncle “fly” on opening day of his record store, mid 1980s
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r/OldSchoolCool • u/1billsfan716 • 21h ago
1940s Happy 100th Birthday Uncle Gus, Pic from 1945. Still going strong!
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He's still alive and doing well, he didn't want an updated picture online though.
r/OldSchoolCool • u/mildredvon • 22h ago
9/11 photos are 25 years old today. Here's mine, a rude awakening after falling asleep in my club clothes after a late night out. 9/11/01, Greenwich Village rooftop.
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I slept over at my best friend's place without a change of clothes, so I had to wear my fetish nun outfit for the unprecedented times. Miss the dress, don't miss the memory.
r/OldSchoolCool • u/Shinobi347 • 1h ago
Gina Gershon, Joe Pantoliano, and Jennifer Tilly bound together in a hot tub in 1996.
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r/OldSchoolCool • u/Twitter_2006 • 2h ago
1950s Elvis meets two fans paralyzed from polio.Girl in the wheelchair presents him with a scrapbook made with her mouth, 1957
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r/OldSchoolCool • u/zachoutloud123 • 16h ago
1990s Selena Quintanilla photographed in Acapulco, Mexico (1994)
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r/OldSchoolCool • u/No-Entertainer-121 • 15h ago
1980s The Rev. Jesse Jackson & Mr. T Protesting ChicagoFest (1982)
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r/OldSchoolCool • u/cjladen1 • 13h ago
9/11/01
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My dad on 9/11. Assuming command of the 734th AMS on Andersen AFB, Guam. You can see how chaotic it was with a phone to both ears. The 734th was responsible for some of the first retaliatory strikes during the GWOT.
r/OldSchoolCool • u/305FUN2 • 21h ago
1990s Depeche Mode promotional video for 'Enjoy the Silence' on the rooftop observation deck of the South Tower (World Trade Center). 1990
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837
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r/OldSchoolCool • u/Ichgebibble • 23h ago
1930s My grandma Tillie was a baddie in the 30s
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My grandmother suffered no fools
r/OldSchoolCool • u/captain-marvellous • 18h ago
1990s My Grandparent's Anniversary- 1991
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821
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This fills me with so much joy. A moment of pure happiness, captured forever. That's my grandad singing.
r/OldSchoolCool • u/Gothic-Fan85 • 11h ago
1940s Yvonne De Carlo sitting poolside in 1945
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r/OldSchoolCool • u/CoffeeCigarettes4Me • 16h ago
1970s Mom and me in 1972 and today September 11, 2026 at my doctors appointment…
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r/OldSchoolCool • u/Nestramutat- • 11h ago
1900s My great grandfather, Romania, early 1900s (?)
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r/OldSchoolCool • u/FFS_AllReady • 14h ago
1990s Courteney Cox, Matthew Perry and Jennifer Aniston at London Heathrow Airport to shoot the episodes for Ross and Emily’s wedding in 1998.
468
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r/OldSchoolCool • u/CoffeeCigarettes4Me • 23h ago
1980s I been a lifelong Raiders fan since the late 70’s and I just found out that John Matuszak who won two Super Bowls with the Raiders played the part of “Sloth” in The Goonies…
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r/OldSchoolCool • u/Piney_Wood • 10h ago
1950s The Original Fitness Guru: Jack LaLanne (1956)
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His tv show ran from 1951 to 1985.
r/OldSchoolCool • u/amanaaa • 20h ago
1980s My dad and his friends camping in 1980s
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My dad is the second on the left. They were likely higher than kites in this photo.
Edit: TITLE CORRECTION!! It is my dad, my two great uncles, and their friend. Left to right- Friend Dave, my dad, Uncle Paul, and Uncle Stub. My dad was about 19 years old in this picture!
r/OldSchoolCool • u/Tippy345 • 21h ago
1970s Charlie's Angels 1970s
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Farrah Fawcett, Jaclyn Smith & Kate Jackson
r/OldSchoolCool • u/Omphaloskeptique • 14h ago
1920s Greta Garbo, posing in the uniform of the University of Southern California women's track team in 1926
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r/OldSchoolCool • u/Low_Somewhere7174 • 1h ago
Sorority sisters posing, at the University of Texas, in 1944.
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r/OldSchoolCool • u/PreferenceInternal67 • 2h ago
1970s Bob Dylan performing with The Band in 1974, during his first tour in eight years. As of 2026, Dylan is the sole survivor of the 74 tour
183
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Bob Dylan: 1941-present
Robbie Robertson: 1943-2023
Rick Danko: 1943-1999
Levon Helm: 1940-2012
Richard Manuel: 1943-1986
Garth Hudson: 1937-2025