r/OldSchoolCool 12h ago Silver Wholesome

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

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28.3k Upvotes

r/OldSchoolCool 8h ago

Robin Williams with daughter Zelda 1989

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2.1k Upvotes

r/OldSchoolCool 20h ago Helpful

Monty Python 1976

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15.8k Upvotes

r/OldSchoolCool 18h ago Silver Wholesome

Graham Chapman's Eulogy by John Cleese (1989)

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8.1k Upvotes

r/OldSchoolCool 6h ago

Gillian Anderson 90s

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486 Upvotes

r/OldSchoolCool 10h ago

Danny Trejo at Muscle Beach. 1980s

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654 Upvotes

r/OldSchoolCool 54m ago

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

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Upvotes

r/OldSchoolCool 16h ago

Mulholland Falls (1996)

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1.7k Upvotes

r/OldSchoolCool 9h ago

70s foxy chicks!

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462 Upvotes

r/OldSchoolCool 3h ago

Movies directed by George Méliès (ca.1902)

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116 Upvotes

r/OldSchoolCool 10h ago

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

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425 Upvotes

r/OldSchoolCool 1h ago

Kerri Hoskins as Sonya Blade MK3 1994

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Upvotes

r/OldSchoolCool 23h ago Silver Got the W

My wife and I on our third date, 1985

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4.5k Upvotes

r/OldSchoolCool 2h ago

Robin Williams outside The Comedy Store in Hollywood, 1978

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74 Upvotes

r/OldSchoolCool 3h ago

Pablo Picasso dressed as Popeye, 1957

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96 Upvotes

r/OldSchoolCool 2h ago

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

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70 Upvotes

r/OldSchoolCool 19h ago Wholesome Masterpiece

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

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1.5k Upvotes

r/OldSchoolCool 1h ago

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

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Upvotes

r/OldSchoolCool 1h ago

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

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Upvotes

r/OldSchoolCool 14h ago

Punk with AK-47 in Bosnian War, 1992.

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428 Upvotes

r/OldSchoolCool 5h ago Wholesome (Pro)

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

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91 Upvotes

r/OldSchoolCool 43m ago I'll Drink to That

Brigitte Bardot at Cannes 1953

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Upvotes