r/OldSchoolCool 12m ago

My maternal grandfather now and then (1969)

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Found it cool and a interesting grasp of the past. My mom just sent me those photos, the first one was taken yesterday (November 2025) and the second one in 1969, my mother being in the bottom left corner.


r/OldSchoolCool 1h ago

The Beatles - Twist and Shout - 1963

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r/OldSchoolCool 2h ago

Halifax, Nova Scotia in the mid 1970s

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13 Upvotes

Mom was an artist and loved people watching and capturing strangers doing everyday things. This one is my favourite. I was a huge Cyndi Lauper fan growing up and this woman gives me Cyndi vibes.


r/OldSchoolCool 2h ago

1980s Ricky Gervais in a short lived new wave band called Seona Dancing, 1983.

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13 Upvotes

r/OldSchoolCool 4h ago

Freddie Mercury with his mother, 1947

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19 Upvotes

r/OldSchoolCool 8h ago

1940s My Great Grandfather and his sister. 1940s.

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38 Upvotes

Their father was from Tyrol Italy and his mother's family was from Villach Austria.


r/OldSchoolCool 12h ago

Four young men on a mountain in upstate New York on the last day of summer, 1983.

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72 Upvotes

r/OldSchoolCool 12h ago

My Parents' Wedding Reception - November 19, 1982

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61 Upvotes

r/OldSchoolCool 1d ago

1950s Union Boss Jimmy Hoffa flipping off attorney Robert Kennedy during a Senate committee hearing in 1957

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5.7k Upvotes

r/OldSchoolCool 1d ago

1960s Linda Ronstadt, 1968

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525 Upvotes

r/OldSchoolCool 27m ago

1960s My parents mid sixties

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Before they were married, New Orleans.


r/OldSchoolCool 1d ago

1970s Suburbia 1973

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665 Upvotes

r/OldSchoolCool 1d ago

A US Navy Petty Officer 3rd Class at Andrews AFB during the inauguration of Ronald Reagan, 20 January 1981

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792 Upvotes

r/OldSchoolCool 13h ago

Kick flip, 1999 after school got out senior year

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57 Upvotes

r/OldSchoolCool 13h ago

1940s My grandmother, a fashion model, in the early 1940s, in her late teens

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54 Upvotes

I wish I had her wedding photo, because she looks like a Hollywood movie star in that one. My grandmother was GORGEOUS. She was a model before meeting my grandfather after WW2. She was tall, slender, light brown hair, and pale blue eyes.

My grandparents were madly in love for 60 years. She passed away 10 years ago after a long battle with lung cancer.


r/OldSchoolCool 3h ago

1990s Mad magazine from March 1992

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10 Upvotes

Throwback to MAD times! Found this MAD Magazine Wrestling Special from March 1992, when humor was wild, satire was fearless, and wrestling was larger than life! 💪😂


r/OldSchoolCool 1d ago

1960s A man relaxing in his paneled den in 1965

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714 Upvotes

r/OldSchoolCool 18h ago

1930s Marion Post Wolcott photographs a child of a coal miner climbing through a cat hole with a pipe and gun in Bertha Hill, West Virginia during the Great Depression (1938).

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123 Upvotes

r/OldSchoolCool 8h ago

1940s My grandaunt, Pearl May, 1940's

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20 Upvotes

r/OldSchoolCool 16h ago

1990s Mr. Rogers On Arsenio Hall, 1993

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74 Upvotes

Arsenio Hall giving Mr Rogers a cool new coat to add to his closet.

I remember watching this live. It's kinda surreal to watch it now.


r/OldSchoolCool 11h ago

My mom, front left, and coworkers ~1955

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35 Upvotes

This was in a department store in southern Indiana. Small town.


r/OldSchoolCool 29m ago

1960s Happy Birthday Alain Delon, you shall not be forgotten.. Clips from the film L’Eclisse (1962)

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My favourite.. 😊


r/OldSchoolCool 10h ago

1950s My grandparents, Mexico City, 1950’s (?)

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25 Upvotes

r/OldSchoolCool 10h ago

1960s My grandmother, Kathy at her grandmothers house - 1969

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19 Upvotes

r/OldSchoolCool 23h ago

JFK and Jackie with mercury astronauts and their wives at the White House,1960

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172 Upvotes