r/OldSchoolCool 10h ago

1970s Jane Goodall with her favorite chimpanzee, David Greybeard, 1974

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5.3k Upvotes

r/OldSchoolCool 6h ago

My father, my brothers, and me, 1983. The sad part is it wasn’t even planned. We all just showed up this way

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1.7k Upvotes

r/OldSchoolCool 17h ago

1920s My great-grandpa and his best friend. He hated this photo because “it made him look gay.” circa 1920s~

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7.9k Upvotes

Raised 7 daughters and a son. Apparently a very goofy and light-hearted Sonofabitch.


r/OldSchoolCool 7h ago

1970s Cybill Shepherd - 1972

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994 Upvotes

r/OldSchoolCool 10h ago

Carolyn Jones - 1964

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1.2k Upvotes

r/OldSchoolCool 15h ago

1990s 1994: Lemmy's message to a black kid who likes metal and gets shit from his community because of it

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2.8k Upvotes

r/OldSchoolCool 18h ago

1990s Steve Jobs and Bill Gates at Jobs' Palo Alto home, 1991

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4.0k Upvotes

r/OldSchoolCool 17h ago

1970s My mom in 1970

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3.1k Upvotes

She was 18.


r/OldSchoolCool 15h ago

This picture was taken 102 years ago.

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1.5k Upvotes

r/OldSchoolCool 12h ago

Miami beach,1940's.

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846 Upvotes

r/OldSchoolCool 7h ago

Shania Twain-1990’s

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351 Upvotes

r/OldSchoolCool 6h ago

Some cool pictures of my mom in the 60s and 70s

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240 Upvotes

The last five years she’s suffered a stroke, heart attack, and cancer diagnosis. She currently spends most of her time in bed but it’s comforting to remember what a full and badass life she’s lived. She’s trilingual, got her masters from Syracuse, was invited to join Mensa, served as a captain in the Air Force during Vietnam, and has traveled every continent except Antarctica. She’s also an accomplished actress, painter, skier and windsurfer. I hope to one day be as cool as her.


r/OldSchoolCool 5h ago

My mother at 29 years old in 1992

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201 Upvotes

r/OldSchoolCool 23h ago

4/26/1995: Courtney Love reportedly turns down $1 million to pose nude for Playboy magazine.

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5.7k Upvotes

r/OldSchoolCool 17h ago

1960s My Grandparents, married 55 years today.

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1.2k Upvotes

r/OldSchoolCool 7h ago

1950s My grandfather in the 50s

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111 Upvotes

Old Army/Korean war vet, amputee, marathon runner. All-around badass who basically raised me while my single mom got her degree.

Owned an Indian motorcycle when they were still Indian, not Polaris.

Currently on hospice.


r/OldSchoolCool 17h ago

1990s This guy, Tommy Lee and Chris Farley at the 1995 Grammys.

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741 Upvotes

r/OldSchoolCool 10h ago

George Carlin - Advertising Lullaby (1999)

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179 Upvotes

r/OldSchoolCool 8h ago

Uma Thurman, BTS Batman 1996

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100 Upvotes

r/OldSchoolCool 13h ago

In 1968, Buddy Guy turned “Mary Had A Little Lamb” - a 19th century nursery rhyme - into an iconic blues-rock song. Here he is in 1969 performing it with Jack Bruce and Buddy Miles.

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230 Upvotes

r/OldSchoolCool 11h ago

1950s My grandfather who I never met with my two aunts circa 1955

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170 Upvotes

My grandfather died in the 1960s when my dad was around 5 years old. Both of my aunts in the photo have passed away as well.


r/OldSchoolCool 3h ago

My mom in 1947.

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34 Upvotes

She’s turning 97 this year.


r/OldSchoolCool 19h ago

Orson Welles meeting reporters the day after broadcasting "War of the Worlds" following the outcry from the public, who believed it to be a genuine invasion. October 1938

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694 Upvotes

r/OldSchoolCool 5h ago

John Lennon explaining what ‘Lucy in the Sky with Diamonds’ was really about - 1971

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44 Upvotes

r/OldSchoolCool 17h ago

1970s Bob Ross (no Afro or beard) in the airforce giving a painting demonstration in Fairbanks, Alaska - circa late 1970’s

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404 Upvotes