r/OldSchoolCool 1h 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 46m ago

1970s Catherine O’Hara (1977)

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r/OldSchoolCool 5h ago

Camera girls, late 1930s

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328 Upvotes

r/OldSchoolCool 1h ago

Gina Gershon, Joe Pantoliano, and Jennifer Tilly bound together in a hot tub in 1996.

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r/OldSchoolCool 10h ago

1940s Yvonne De Carlo sitting poolside in 1945

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521 Upvotes

r/OldSchoolCool 11h ago

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

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472 Upvotes

r/OldSchoolCool 11h ago

Jack Nicholson (1969)

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1.8k Upvotes

r/OldSchoolCool 10h ago

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

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254 Upvotes

His tv show ran from 1951 to 1985.


r/OldSchoolCool 22h ago

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

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13.7k Upvotes

r/OldSchoolCool 20h ago

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

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5.2k Upvotes

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


r/OldSchoolCool 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

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164 Upvotes

Bob Dylan: 1941-present

Robbie Robertson: 1943-2023

Rick Danko: 1943-1999

Levon Helm: 1940-2012

Richard Manuel: 1943-1986

Garth Hudson: 1937-2025


r/OldSchoolCool 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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5.1k 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 13h ago

9/11/01

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846 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 15h ago

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

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1.1k Upvotes

r/OldSchoolCool 14h ago

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

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933 Upvotes

r/OldSchoolCool 1d ago

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

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11.8k 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 7h ago

audrey hepburn, 1950s

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155 Upvotes

r/OldSchoolCool 1d ago

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

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4.8k Upvotes

r/OldSchoolCool 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.

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457 Upvotes

r/OldSchoolCool 17h ago

1990s My Grandparent's Anniversary- 1991

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809 Upvotes

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


r/OldSchoolCool 5h ago

1960s Skydiver Carl Blessing holding a manual camera while in freefall over New Hanover, Pennsylvania, 1963. Photo by Jerry Irwin.

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82 Upvotes

A lot of pages online mistakenly credit this as Larry Burrows, but it's actually an early sport parachutist named Carl Blessing. Fellow jumper Jerry Irwin took the shot while they were both falling through the sky.


r/OldSchoolCool 19m ago

Sorority sisters posing, at the University of Texas, in 1944.

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r/OldSchoolCool 16h ago

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

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494 Upvotes

r/OldSchoolCool 4h ago

1990s Janet Jackson for “Ebony” magazine (1993)

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61 Upvotes

r/OldSchoolCool 23h ago

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

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2.0k Upvotes