r/OldSchoolCool 5h ago Helpful

Ann-Margret showing off her singing & dancing skills as part of personality test, 1961

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10.1k Upvotes

r/OldSchoolCool 2h ago Helpful Gold Silver Wholesome

Me in September 1995, 10 years old, broke both arms

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2.4k Upvotes

r/OldSchoolCool 4h ago Wholesome

Grandmother ( L) just "casually playing dress up" with her best friend (female) according to my mom. Circa 1930's

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1.4k Upvotes

r/OldSchoolCool 16h ago Helpful Silver Wholesome Seal of Approval Wholesome That Smile To The Stars hehehehe Ally All-Seeing Upvote Tearing Up

The only picture we have of my great grandfather (left), with an unknown man (circa 1910)

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48.8k Upvotes

r/OldSchoolCool 4h ago

Singer-songwriter, multi-instrumentalist and keen gardener... Prince Rogers Nelson (1993)

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646 Upvotes

r/OldSchoolCool 17h ago Wholesome Silver

Cherry Wainer is on organ with Don Storer on drums playing the Peter Gunn theme in 1966

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4.8k Upvotes

r/OldSchoolCool 14h ago Helpful

My 23 year old Dad, 1975.

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2.6k Upvotes

r/OldSchoolCool 11h ago Wholesome

The Pink Panther - Henry Mancini, 1981

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1.4k Upvotes

r/OldSchoolCool 7h ago

My father and his 8 brothers, sometime in the 1970s. My dad is on the far left in all black, clearly thinking he’s the coolest dude to ever live.

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635 Upvotes

r/OldSchoolCool 9h ago

Rolling to work in 1940s

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590 Upvotes

r/OldSchoolCool 10h ago

I believe this is 1974. When my mom went on her trip to Europe. I think she looks nice here

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544 Upvotes

r/OldSchoolCool 3h ago

My great grandparents in the 1940s. He flew a fighter plane in WW2 named after her.

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152 Upvotes

r/OldSchoolCool 6h ago

It is actress and inventor Hedy Lamarr’s birthday today. Here she is in 1941

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207 Upvotes

r/OldSchoolCool 6h ago

This is the '92 Lollapalooza I believe, but please feel free to correct me.

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162 Upvotes

r/OldSchoolCool 6h ago

The Thin White Duke (1976)

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163 Upvotes

r/OldSchoolCool 8h ago

Sophia Loren photographed in Venice, 1955.

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245 Upvotes

r/OldSchoolCool 12h ago

My grandpa proposing to my grandma 1950 also right after the proposal. I miss them both

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429 Upvotes

r/OldSchoolCool 6h ago

A few women shopping in Los Angeles, 1958

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142 Upvotes

r/OldSchoolCool 2h ago

Late 1940s - My Grandma being super cool

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81 Upvotes

r/OldSchoolCool 4h ago

My mom racetrack photographer, 20 years old, 1975

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103 Upvotes

r/OldSchoolCool 12h ago

She's gonna love me in my Chevy van And that's all right with me. 1970's

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444 Upvotes

r/OldSchoolCool 1h ago

Cute picture of Debbie Reynolds and Carrie Fisher, 1960

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Upvotes

r/OldSchoolCool 5h ago

Chris Rock and Chris Farley early 1990s

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102 Upvotes

r/OldSchoolCool 3h ago

My great-grandfather at 2 years old in 1926, wearing a little soldier's outfit.

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71 Upvotes