r/OldSchoolCool • • 8h ago

1950s Paula Chandoha photographed by her father Walter in 1955 at their Long Island home.

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1.5k Upvotes

r/OldSchoolCool • • 3h ago

1990s My friend holding a “Homo” sign he kept around his neck at Los Angeles Pride, 1995

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3.7k Upvotes

r/OldSchoolCool • • 2h ago

1990s My high school graduation photo, 1997

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262 Upvotes

I spent the night before trying (and for the most part, failing) to sleep with big velcro rollers in my hair. I don't recommend it.


r/OldSchoolCool • • 10h ago

1980s Andre the Giant and Fred Savage during the making of ‘The Princess Bride’, in 1986.

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405 Upvotes

r/OldSchoolCool • • 8h ago

Actress and inventor Hedy Lamarr posing beside a silver-grey granite bust of herself, sculpted by artist Nina Saemundsson, 1939

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859 Upvotes

r/OldSchoolCool • • 6h ago

Sandra Bullock @ the 1994 MTV VMAs

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408 Upvotes

r/OldSchoolCool • • 9h ago

Back in the 1980's...

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416 Upvotes

We were cool back in the 80's.. Almost 40 yrs later, we're still kinda cool.!!


r/OldSchoolCool • • 21h ago

1990s My wife and I back when we were dating in 1995

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7.6k Upvotes

r/OldSchoolCool • • 12h ago

1990s Danny Trejo and Antonio Banderas on the set of Desperado (1995)

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1.1k Upvotes

r/OldSchoolCool • • 23m ago

1990s Myself and wife around a year after we met 1992

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• Upvotes

r/OldSchoolCool • • 3h ago

My wife with our first child Maggie - 1995

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165 Upvotes

Maggie, AKA the Magpie, Magger Daggers, the Mags. Pound rescue and the smartest dog I've ever seen.


r/OldSchoolCool • • 20h ago

1990s Cameron Diaz ('90) and Snoop Dogg ('89) went to the same high school, Long Beach Polytechnic.

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2.8k Upvotes

She’s claimed that Snoop used to sell her weed


r/OldSchoolCool • • 3h ago

1980s Over 1000 demonstrators organized by Act-Up and Gay and Lesbian Alliance Against Defamation protest the attack of 2 gay men by a group of teens on Broadway which led to numberous arrests of protestors on August 30, 1988

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113 Upvotes

r/OldSchoolCool • • 1h ago

1990s Third Grade 1998-First year w/ glasses

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• Upvotes

r/OldSchoolCool • • 5h ago

1990s Anonymous woman playing Playboy flipper in Paris, early 1990’s

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107 Upvotes

r/OldSchoolCool • • 13h ago

1940s British factory workers on a Cornish beach, Sept 6th, 1943

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501 Upvotes

r/OldSchoolCool • • 20h ago

1982 - my great grandma playing Astrosmash on the Intellivision

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1.4k Upvotes

r/OldSchoolCool • • 1d ago

1980s My Mom & Dad around 1987

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4.4k Upvotes

Mom & dad out on the boat about a year before I joined the party.

Obligatory PSA: drunk boat driving is NOT cool, even though my dad made it look very cool.


r/OldSchoolCool • • 3h ago

A teen girl's style in the 1990s

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64 Upvotes

r/OldSchoolCool • • 22h ago

1980s Kids trading candy after a long night of trick of treating. 1980s

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1.4k Upvotes

r/OldSchoolCool • • 4h ago

1980s My Halloween costumes 1979 to 1988

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54 Upvotes

r/OldSchoolCool • • 6h ago

1960s Back in 1961: My sweet young mom and her first secret love, long before she met and married my dad.

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69 Upvotes

r/OldSchoolCool • • 1d ago

Ryan Gosling, Justin Timberlake, Britney Spears, and Christina Aguilera (The Mickey Mouse Club, 1993)⁠

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5.2k Upvotes

r/OldSchoolCool • • 2h ago

1980s Another candy-sorting photo, Halloween 1982

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31 Upvotes

r/OldSchoolCool • • 59m ago

1980s Dad in the early 80s

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• Upvotes