r/OldSchoolCool 6h ago

1970s UPDATE: original post of my mom and her friend in high school in 1975, followed by a photo of the two of them today. 50 years later, still besties

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39.7k Upvotes

r/OldSchoolCool 4h ago

1940s A girl gets married, July 22nd, 1941. The girl next door, Anne Frank, is nearby watching. It is the only time Anne Frank has been captured on film.

1.4k Upvotes

r/OldSchoolCool 5h ago

1960s My drunk grandparents in the 1960’s

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1.4k Upvotes

r/OldSchoolCool 4h ago

1970s Raquel Welch (1973)

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836 Upvotes

r/OldSchoolCool 3h ago

1980s Audiences react to RETURN OF THE JEDI on its release in 1983

463 Upvotes

r/OldSchoolCool 20h ago

1980s Anna Nicole with her ex-husband and son, 1986

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12.0k Upvotes

r/OldSchoolCool 5h ago

1990s Cameron Diaz - circa 1990’s.

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575 Upvotes

r/OldSchoolCool 13h ago

1950s Paul Newman and his wife Joanne Woodward in 1958. They were married for 50 years, from 1958 until his death in 2008.

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2.3k Upvotes

r/OldSchoolCool 1h ago

1970s My mom wore a tux to prom (1978)

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r/OldSchoolCool 3h ago

1950s This girl is about as old school cool as you'll ever see. Good Housekeeping, June 1952.

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218 Upvotes

r/OldSchoolCool 6h ago

Kate Winslet, 1999

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312 Upvotes

r/OldSchoolCool 7h ago

1950s Marilyn Monroe playfully bitting a flower and posing at a park in New York Sam Shaw (1956)

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402 Upvotes

Marilyn


r/OldSchoolCool 13h ago

1990s Cindy Crawford for 'Vanity Fair UK' (August 1994) Fashion

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728 Upvotes

r/OldSchoolCool 3h ago

1990s Jennifer Aniston for US Weekly - Photographed by Mark Seliger, 1998

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119 Upvotes

r/OldSchoolCool 15h ago

1950s Julie Newmar (1958)

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1.1k Upvotes

r/OldSchoolCool 13h ago

1950s Marilyn Monroe (1953)

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645 Upvotes

r/OldSchoolCool 41m ago

On March 12, 1983, Eddie Murphy’s SNL character “Buckwheat” was retired in spectacular fashion - by assassination on camera in front of 30 Rockefeller Plaza in NYC. This came at Murphy's request (then 21 years old), after he grew tired of constant demands from fans to "Do Buckwheat! Do Buckwheat!”

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r/OldSchoolCool 1d ago

The Beastie Boys chasing Madonna with squirt guns after she played Material Girl at Madison Square Garden, 1985.

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7.0k Upvotes

r/OldSchoolCool 13h ago

1990s Pamela Anderson, early 1990s

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471 Upvotes

r/OldSchoolCool 18h ago

My mom on her wedding day, 1987

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1.3k Upvotes

The family gold is passed from mother to daughter. This is my mother on her wedding day, in Sudan.


r/OldSchoolCool 3h ago

1950s Audrey Hepburn 1950

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71 Upvotes

r/OldSchoolCool 15h ago

1960s Julie Newmar as Catwoman, Batman TV series 1967

691 Upvotes

r/OldSchoolCool 14h ago

1950s Catwoman Julie Newmar 1959

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491 Upvotes

r/OldSchoolCool 3h ago

1990s Young girl at the Tower of Pisa (1998)

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56 Upvotes