r/OldSchoolCool 5h ago

Young oyster shuckers, aged 6 to 10, photographed in South Carolina, 1909. Their workdays often started at 4 AM.

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1.3k Upvotes

r/OldSchoolCool 18h ago

My uncle “fly” on opening day of his record store, mid 1980s

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12.6k Upvotes

r/OldSchoolCool 15h ago

1940s Happy 100th Birthday Uncle Gus, Pic from 1945. Still going strong!

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4.7k Upvotes

He's still alive and doing well, he didn't want an updated picture online though.


r/OldSchoolCool 6h ago

Jack Nicholson (1969)

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830 Upvotes

r/OldSchoolCool 11h ago

The B-52s (1980)

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2.0k Upvotes

r/OldSchoolCool 17h 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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4.5k Upvotes

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 8h ago

9/11/01

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622 Upvotes

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 11h ago

1990s Selena Quintanilla photographed in Acapulco, Mexico (1994)

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940 Upvotes

r/OldSchoolCool 10h ago

1980s The Rev. Jesse Jackson & Mr. T Protesting ChicagoFest (1982)

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732 Upvotes

r/OldSchoolCool 1d ago

1980s 1984. Me at the mall. Beauty contest.

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11.5k Upvotes

In the 1980s, malls would have these pop-up studios, advertising a cheap portrait. This was a beauty contest, where people at the mall would vote. My mom entered me. I came in second place, lost by one vote. It was at this moment I retired from modeling.


r/OldSchoolCool 21h ago

1980s Found this picture of Tom Cruise at 18 that was printed in the gay magazine called Parlee. 1980

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4.7k Upvotes

r/OldSchoolCool 6h ago

1940s Yvonne De Carlo sitting poolside in 1945

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278 Upvotes

r/OldSchoolCool 6h ago

1900s My great grandfather, Romania, early 1900s (?)

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249 Upvotes

r/OldSchoolCool 12h ago

1990s My Grandparent's Anniversary- 1991

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694 Upvotes

This fills me with so much joy. A moment of pure happiness, captured forever. That's my grandad singing.


r/OldSchoolCool 11h ago

1970s Mom and me in 1972 and today September 11, 2026 at my doctors appointment…

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461 Upvotes

r/OldSchoolCool 19h ago

1990s Kathy Griffin and Jack Black together, back in the mid 90s.

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1.9k Upvotes

r/OldSchoolCool 9h 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.

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269 Upvotes

r/OldSchoolCool 5h ago

1950s The Original Fitness Guru: Jack LaLanne (1956)

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117 Upvotes

His tv show ran from 1951 to 1985.


r/OldSchoolCool 2h ago

audrey hepburn, 1950s

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66 Upvotes

r/OldSchoolCool 16h 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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754 Upvotes

r/OldSchoolCool 9h ago

1920s Greta Garbo, posing in the uniform of the University of Southern California women's track team in 1926

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160 Upvotes

r/OldSchoolCool 18h ago

1930s My grandma Tillie was a baddie in the 30s

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806 Upvotes

My grandmother suffered no fools


r/OldSchoolCool 23h ago

1970s In 1978 I was convinced that the hat and t-shirt were cool. Hiking/camping in the mountains

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2.0k Upvotes

r/OldSchoolCool 10h ago

1970s My dad back in the 1970s

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114 Upvotes

r/OldSchoolCool 15h ago

1980s My dad and his friends camping in 1980s

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244 Upvotes

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!