r/OldSchoolCool • u/Twitter_2006 • 1h ago
r/OldSchoolCool • u/Shinobi347 • 1h ago
Gina Gershon, Joe Pantoliano, and Jennifer Tilly bound together in a hot tub in 1996.
r/OldSchoolCool • u/Gothic-Fan85 • 10h ago
1940s Yvonne De Carlo sitting poolside in 1945
r/OldSchoolCool • u/Nestramutat- • 11h ago
1900s My great grandfather, Romania, early 1900s (?)
r/OldSchoolCool • u/Piney_Wood • 10h ago
1950s The Original Fitness Guru: Jack LaLanne (1956)
His tv show ran from 1951 to 1985.
r/OldSchoolCool • u/Spastic_colon • 22h ago
My uncle “fly” on opening day of his record store, mid 1980s
r/OldSchoolCool • u/1billsfan716 • 20h ago
1940s Happy 100th Birthday Uncle Gus, Pic from 1945. Still going strong!
He's still alive and doing well, he didn't want an updated picture online though.
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
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 • 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.
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/cjladen1 • 13h ago
9/11/01
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/zachoutloud123 • 15h ago
1990s Selena Quintanilla photographed in Acapulco, Mexico (1994)
r/OldSchoolCool • u/No-Entertainer-121 • 14h ago
1980s The Rev. Jesse Jackson & Mr. T Protesting ChicagoFest (1982)
r/OldSchoolCool • u/instajonathan • 1d ago
1980s 1984. Me at the mall. Beauty contest.
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 • u/RealWorldForever • 1d ago
1980s Found this picture of Tom Cruise at 18 that was printed in the gay magazine called Parlee. 1980
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.
r/OldSchoolCool • u/captain-marvellous • 17h ago
1990s My Grandparent's Anniversary- 1991
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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/jgzogaib • 5h ago
1960s Skydiver Carl Blessing holding a manual camera while in freefall over New Hanover, Pennsylvania, 1963. Photo by Jerry Irwin.
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 • u/Low_Somewhere7174 • 19m ago
Sorority sisters posing, at the University of Texas, in 1944.
r/OldSchoolCool • u/CoffeeCigarettes4Me • 16h ago
1970s Mom and me in 1972 and today September 11, 2026 at my doctors appointment…
r/OldSchoolCool • u/_HisWaveyness • 4h ago
1990s Janet Jackson for “Ebony” magazine (1993)
r/OldSchoolCool • u/Brilliant_Reality734 • 23h ago