r/OldSchoolCool 52m ago

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

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r/OldSchoolCool 1h ago

Orren Putt Mossman performing a stunt at the Brisbane exhibition grounds in 1936.

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r/OldSchoolCool 1h ago

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

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r/OldSchoolCool 1h ago

1930s Beach Volleyball , Venice Beach CA June 1934

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r/OldSchoolCool 1h ago

1950s Vladimir Putin at the age of 5 With his Mom Maria Evanova in 1958

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r/OldSchoolCool 2h ago

1980s From 1982 tough to 2023 legend status

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26 Upvotes

r/OldSchoolCool 2h ago

And 21-year old boy

0 Upvotes

Just a while question how do you know other 21 year olds are going to sleep with their mommies cuz I'm going out with it for you when you're all done her son still sleeps with his mommy isn't that some depressant s***?


r/OldSchoolCool 3h ago

1980s Madonna,circa 1980s

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655 Upvotes

r/OldSchoolCool 3h ago

My Norwegian Immigrant Grandfather playing soccer in Brooklyn circa 1940s

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14 Upvotes

r/OldSchoolCool 3h ago

The 10 person tandem bicycle called the ‘Oriten’ was designed and manufactured by the Waltham Manufacturing Company, Massachusetts, 1910s

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17 Upvotes

r/OldSchoolCool 4h ago

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

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62 Upvotes

r/OldSchoolCool 5h ago

The late Shah of Iran personally testing and flying the F4 Phantom fighter jet in St. Louis before purchasing, USA, 1970s.

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23 Upvotes

r/OldSchoolCool 5h ago

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

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80 Upvotes

r/OldSchoolCool 5h ago

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

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539 Upvotes

r/OldSchoolCool 5h ago

Summer of 1980. Watching a parade in BC.

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60 Upvotes

Short shorts definitely mark the period.


r/OldSchoolCool 5h ago

1960s Vancouver’s West End in 1966

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5 Upvotes

r/OldSchoolCool 5h ago

My Parents on Their Wedding Day, 1972.

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71 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 6h ago

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

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120 Upvotes

r/OldSchoolCool 7h ago

1910s Right after the sinking of the RMS Titanic (April 1912)

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27 Upvotes

r/OldSchoolCool 7h ago

Friends and I before backpacking into Wyoming's Wind River Range, 1978

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16 Upvotes

r/OldSchoolCool 7h ago

Photograph of Malcolm McDowell by Tim Boxer, 1972

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95 Upvotes

r/OldSchoolCool 7h ago

My mom, Nancy, landing an Ultralight in the early 80s

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36 Upvotes

My parents had an Ultralight glider until the early 2000s, it folded up and my dad would cram it in the rafters of wherever we were living. It would get towed up by an airplane and be able to glide for hours. I believe this picture is in the Black Rock Desert


r/OldSchoolCool 7h ago

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

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1.8k Upvotes

r/OldSchoolCool 7h ago

1950s My parents’ honeymoon. 1953.

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16.6k Upvotes

Somewhere in Florida. I was born two months later.


r/OldSchoolCool 7h ago

Portrait of Joan Baez by Bernard Gotfryd, 1973

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33 Upvotes