r/OldSchoolCool • u/OnlyLoneWolfTV • 14h ago
1952 Rockabilly dance
When you realize you grandparents were far cooler then you’ll ever be!
r/OldSchoolCool • u/qning • 11h ago
Me in a members only jacket and a monkey in a space suit. Somewhere in Spain, probably Madrid. Early 1980s.
r/OldSchoolCool • u/EarlGrey_Picard • 20h ago
Lucille Ball and Desi Arnaz outside their production studio in 1958. Lucy would go on to buy and produce a series called Star Trek when everyone else passed on it.
r/OldSchoolCool • u/GamesterOfTriskelion • 11h ago
Robert Stack, who would go on to host Unsolved Mysteries, in 1978.
r/OldSchoolCool • u/NationYell • 2h ago
Michael Caine and his mum in 1966
r/OldSchoolCool • u/InsomuchIdle • 17h ago
The night they ended Prohibition, December 5th 1933.
r/OldSchoolCool • u/AtlasShrunked • 21h ago
Me & my girlfriend in the 1980s, she was like a famous supermodel or something but was always traveling for photo shoots, that's why it didn't work out
r/OldSchoolCool • u/ShallWeRiot • 1d ago
My parents wedding photos  a slightly different take, but my dad's biggest rebellion was bringing home and marrying a white woman. His expression says it all.
Kinda happy, but also resolute, and ready to throw a fit if they started dissing my mum in Cantonese. And his glasses oh my gosh hahaha. And that headress in the second pic
r/OldSchoolCool • u/Phallus_Maximus69E • 8h ago
Greek model Aliki Diplarakou, who previously won the title of Miss Hellas and Miss Europe 1930, as Athena Promachos at the Second Delphic Festival in Delphi, 1930.🦉
r/OldSchoolCool • u/LetPsychological2683 • 13h ago
My Mongolian dad in Germany 1987
r/OldSchoolCool • u/Iranianveranda500 • 3h ago
Sigourney Weaver, 1983. NSFW
r/OldSchoolCool • u/dittidot • 20h ago
My family before an early start to our vacation, 1963
r/OldSchoolCool • u/singleguy79 • 11h ago
Dolly Parton in the 1960s
r/OldSchoolCool • u/klippo55 • 2h ago
vin diesel at school 1985
r/OldSchoolCool • u/ninacristalxxx • 48m ago
Bill Withers and his band, super cool old school! Use Me, 1972
r/OldSchoolCool • u/dogbytes • 7h ago
My wife and I back in 1968, back when I was in the US Army, still together.
r/OldSchoolCool • u/Droc20 • 14h ago
Me and my Dad at my b-day bout 1985. I know yall see the abs
r/OldSchoolCool • u/Mad_Season_1994 • 11h ago
Led Zeppelin at Madison Square Garden in 1973 (song is Over the Hills and Far Away)
r/OldSchoolCool • u/Soopreme_Being • 14h ago
My grandfather during WW1
r/OldSchoolCool • u/NutmegOnEverything • 14h ago
My grandfather, late 70s, today would have been his 100th birthday
r/OldSchoolCool • u/waitingforthesun92 • 15h ago
Stevie Ray Vaughan: the only man that could transform “Mary Had A Little Lamb” into an epic blues-rock song. (1983)
r/OldSchoolCool • u/tenaciousdeev • 23h ago
Rare photo of Robin Williams and George Carlin together in the mid 90's
r/OldSchoolCool • u/eaglemaxie • 8h ago
Pantheon museum visitors inside the only ancient Roman building that has remained intact for over 2,000 years, photo by Thomas Struth, 1990
r/OldSchoolCool • u/Reddit_Survivor9 • 1d ago
Pierce Brosnan interview June 1985
r/OldSchoolCool • u/violableGranule20 • 17h ago