r/OldSchoolCool • u/bidge8 • 12h ago

Michael Jordan's iconic 'Free Throw Line' dunk, 1988.

r/OldSchoolCool • u/draconetzah • 8h ago

Robin Williams with daughter Zelda 1989

r/OldSchoolCool • u/Bunnes68 • 20h ago

Monty Python 1976

r/OldSchoolCool • u/fatihisi • 18h ago

Graham Chapman's Eulogy by John Cleese (1989)

r/OldSchoolCool • u/Bunnes68 • 6h ago

Gillian Anderson 90s

r/OldSchoolCool • u/Browndog888 • 10h ago

Danny Trejo at Muscle Beach. 1980s

r/OldSchoolCool • u/Shark-Farts • 54m ago

12-year-old budding actor Christopher Walken making pie crust in his father's bakery

r/OldSchoolCool • u/el_maziello • 16h ago

Mulholland Falls (1996)

r/OldSchoolCool • u/SeasonedTimeTraveler • 9h ago

70s foxy chicks!

r/OldSchoolCool • u/ALoBoi_Music • 3h ago

Movies directed by George Méliès (ca.1902)

r/OldSchoolCool • u/RogerTheAliens • 10h ago

1988 Michael J. Fox and Susanna Hoffs, singer of the Bangles.

r/OldSchoolCool • u/MadMasterMad • 1h ago

Kerri Hoskins as Sonya Blade MK3 1994

r/OldSchoolCool • u/joecooool418 • 23h ago

My wife and I on our third date, 1985

r/OldSchoolCool • u/theironman46 • 2h ago

Robin Williams outside The Comedy Store in Hollywood, 1978

r/OldSchoolCool • u/Chilipepah • 3h ago

Pablo Picasso dressed as Popeye, 1957

r/OldSchoolCool • u/sagar9175 • 2h ago

Jenny Joseph poses for the iconic 'Columbia Pictures' logo,1992

r/OldSchoolCool • u/bhutapati • 19h ago

John Singer Sargent's 'Portrait of Madame X,' which caused scandal and controversy in 1884

r/OldSchoolCool • u/DiosMioMan63 • 1h ago

You know that at some point this guy told someone “ass, gas, or grass” (1970s)

r/OldSchoolCool • u/DiosMioMan63 • 1h ago

Portrait of Ah-Weh-Eyu (Pretty Flower), of the Seneca nation, 1908. Photo by J.L. Blessing.

r/OldSchoolCool • u/I_am_Mr_Knowitall • 14h ago

Punk with AK-47 in Bosnian War, 1992.

r/OldSchoolCool • u/charlyhallak • 5h ago

My parents. 1978 while engaged and 2021 42 years into their marriage

r/OldSchoolCool • u/Ready1377 • 43m ago

Brigitte Bardot at Cannes 1953