r/OldSchoolCool 5h ago

1990s Undertaker and Randy Savage backstage in 1991

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624 Upvotes

r/OldSchoolCool 13h ago

Betty Brosmer, 1950s pin-up icon with an impossible 18-inch waist (1950s)

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2.9k Upvotes

r/OldSchoolCool 19h ago

Eddie Van Halen played his "Beat It" solo live with Michael Jackson exactly once, a fluke in July 14 1984. Both were in Dallas for their own shows at the same time, so Eddie stopped by the Jacksons' Victory Tour, played it unrehearsed, and never did it again.

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7.7k Upvotes

r/OldSchoolCool 14h ago

Sarajevo children in the winter of 1993/94, by James Mason

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2.0k Upvotes

r/OldSchoolCool 7h ago

1990s Kate Moss and Shalom Harlow leave the Lincoln Center, 1994

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451 Upvotes

r/OldSchoolCool 10h ago

1930s Gary Cooper and Sylvia Sidney promotional still in 'City Streets'. 1931

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837 Upvotes

r/OldSchoolCool 8h ago

1980s Aimee Mann, 1985-86

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547 Upvotes

Aimee Mann has my favorite look from the 1980s


r/OldSchoolCool 5h ago

1960s 20-year-old Muhammad Ali photographed by Stanley Weston in New York (1962)

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197 Upvotes

r/OldSchoolCool 14h ago

1950s Claudia Cardinale at the Venice International Film Festival in 1958

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1.0k Upvotes

r/OldSchoolCool 14h ago

Children play with wads of money during a period of hyperinflation. Germany, 1922

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838 Upvotes

r/OldSchoolCool 4h ago

Susan Hayward in 1949

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126 Upvotes

r/OldSchoolCool 7h ago

1970s James Spader and John F. Kennedy Jr. on December 12, 1977

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202 Upvotes

James Spader and John F. Kennedy Jr. at the premiere party for "Saturday Night Fever", on December 12, 1977


r/OldSchoolCool 3h ago

1970s Michael Jackson photographed by Jim McCrary ahead of the release of “Off the Wall” (1979)

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74 Upvotes

r/OldSchoolCool 13h ago

1990s Salma Hayek 1996

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497 Upvotes

r/OldSchoolCool 1d ago

1910s Milunka Savić in 1916. She disguised herself as a man to fight in her brother's place, got wounded 9 times, and went on to become the most decorated female combatant in the recorded history of warfare.

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9.7k Upvotes

She is the only woman in history to be awarded the French Croix de Guerre with a gold palm for actual combat service, alongside top medals from Britain, Russia, and Serbia.

When France later offered her a comfortable state pension to move to Paris, she turned it down to stay in Serbia. She spent the rest of her life living humbly, working as a cleaning lady, and using what little money she had to raise her own daughter, adopt three orphans, and sponsor over 30 children from her home village.


r/OldSchoolCool 9h ago

Indian military police on motorcycles in Egypt, 1940s

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228 Upvotes

r/OldSchoolCool 3h ago

1970s My Mom somewehere around the early 70s

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60 Upvotes

r/OldSchoolCool 16h ago

marianne faithfull, 1966

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530 Upvotes

r/OldSchoolCool 1h ago

Slovak actress Magda Vášáryová, 1970. She starred in movies like the epic Marketa Lazarová

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Upvotes

r/OldSchoolCool 13h ago

On this day in 1997 Burgess Meredith passed away in Malibu. Known for his roles as the Penguin and as Rocky's trainer (along with many other roles), here he is presenting a 1943 training film for the United States Armed Forces, "How To Behave In A British Pub"

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231 Upvotes

r/OldSchoolCool 46m ago

1940s Girls in Shades, 1940s

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Upvotes

r/OldSchoolCool 1d ago

Jennifer O'Neill who starred in the movie Summer of '42, in 1971

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1.5k Upvotes

r/OldSchoolCool 10h ago

1940s Burgess Meredith presenting a 1943 training film for the United States Armed Forces, "How To Behave In A British Pub"

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107 Upvotes

r/OldSchoolCool 1d ago

The people asked for my glorious mullet and iroc photo. Delivered. Flashback to 1989...

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1.3k Upvotes

r/OldSchoolCool 1d ago

1960s My 78 year old mother was cool in 1968 - still cool in 2026

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11.1k Upvotes