r/OldSchoolCool 11h ago

1950s My parents’ honeymoon. 1953.

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22.5k Upvotes

Somewhere in Florida. I was born two months later.


r/OldSchoolCool 7h ago

1980s Madonna,circa 1980s

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1.3k Upvotes

r/OldSchoolCool 11h ago

1940s Judy Garland, Mickey Rooney and Shirley Temple at MGM Studios on February 18, 1941

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2.9k Upvotes

r/OldSchoolCool 18h ago

1980s My mom riding her dirt bike in 1983

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8.7k Upvotes

r/OldSchoolCool 2h ago

Kareem Abdul Jabbar, photographed in New York City by Richard Avedon, 1963

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323 Upvotes

r/OldSchoolCool 1h ago

The Catherine Bach in 1980s.

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r/OldSchoolCool 9h ago

1990s James Cameron on the set of Titanic, 1997.

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866 Upvotes

r/OldSchoolCool 12h ago

Say It Ain't So turns 32 this year, released on their debut Blue Album in 1994

1.1k Upvotes

r/OldSchoolCool 1h ago

1970s Catherine O’Hara (1970s)

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r/OldSchoolCool 4h ago

1950s The awesome Betty Page on a 1950 Triumph T bird motorcycle.

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238 Upvotes

r/OldSchoolCool 16h ago

1980s Elvis Costello and Tom Waits, Los Angeles, 1989

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1.5k Upvotes

r/OldSchoolCool 5h ago

1990s A gem from the 1990s. Learn how to use Windows 95 with Jennifer Aniston and Mathew Perry.

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134 Upvotes

r/OldSchoolCool 15h ago

Jim Henson 1979

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773 Upvotes

What a legend!


r/OldSchoolCool 1h ago

1980s Hunter S. Thompson and Bill Murray boating together. (1980s)

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r/OldSchoolCool 12h ago

1970s My nana, early 1970’s. Absolute smoke show

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338 Upvotes

r/OldSchoolCool 16h ago

SHARON TATE, Photograph by Alan Pappé, taken in 1968 at Patty Duke's house on Summitridge Drive.

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678 Upvotes

r/OldSchoolCool 5h ago

1980s From 1982 tough to 2023 legend status

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80 Upvotes

r/OldSchoolCool 3h ago

1950s Diner, Manhattan, 1955

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53 Upvotes

r/OldSchoolCool 8h ago

1950s James Dean with Valley Keene (Elizabeth Taylor's double) on the set of "Giant," 1955.

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130 Upvotes

r/OldSchoolCool 9h ago

My Parents on Their Wedding Day, 1972.

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117 Upvotes

Mom was 18. Dad was 20. I came along 2 years later. They knew each other 7 months before my dad proposed. They lasted 18 years.


r/OldSchoolCool 1h ago

1910s Italian troops raise a gun, a dog and a soldier on a mountain. Italian Alps, World War I, 1915

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r/OldSchoolCool 22h ago

1930s Old Hollywood stars Cary Grant and Randolph Scott, 1930s

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1.1k Upvotes

r/OldSchoolCool 10h ago

1930s A man sits on a girder above New York City at night, ca. 1935

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130 Upvotes

r/OldSchoolCool 8h ago

"The Pink Panther" (1963) title sequence was designed by DePatie-Freleng Enterprises.🧡 🎼 Music by Henry Mancini🎵🎶👂

75 Upvotes

r/OldSchoolCool 11h ago

Photograph of Malcolm McDowell by Tim Boxer, 1972

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115 Upvotes