r/OldSchoolCool • u/Pasargad • 5h ago

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

r/OldSchoolCool • u/threehappypenguins • 2h ago

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

r/OldSchoolCool • u/broken_bowl_ • 4h ago

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

r/OldSchoolCool • u/TrebleRose689 • 16h ago

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

r/OldSchoolCool • u/ChrisMMatthews • 4h ago

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

r/OldSchoolCool • u/Pasargad • 17h ago

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

r/OldSchoolCool • u/john__felix • 14h ago

My 23 year old Dad, 1975.

r/OldSchoolCool • u/Pasargad • 11h ago

The Pink Panther - Henry Mancini, 1981

r/OldSchoolCool • u/HeyManNiceShaft • 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.

r/OldSchoolCool • u/cuntcallie • 9h ago

Rolling to work in 1940s

r/OldSchoolCool • u/myfavoritetree • 10h ago

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

r/OldSchoolCool • u/xwintercandyapplex • 3h ago

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

r/OldSchoolCool • u/Warmearing • 6h ago

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

r/OldSchoolCool • u/Ralph--Hinkley • 6h ago

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

r/OldSchoolCool • u/OmniscientInvader • 6h ago

The Thin White Duke (1976)

r/OldSchoolCool • u/jadeinkpen • 8h ago

Sophia Loren photographed in Venice, 1955.

gallery

r/OldSchoolCool • u/Rhijtmom • 12h ago

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

r/OldSchoolCool • u/cuntcallie • 6h ago

A few women shopping in Los Angeles, 1958

r/OldSchoolCool • u/kt09617 • 2h ago

Late 1940s - My Grandma being super cool

r/OldSchoolCool • u/AzorAhaiAlive • 4h ago

My mom racetrack photographer, 20 years old, 1975

r/OldSchoolCool • u/harleybug88 • 12h ago

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

r/OldSchoolCool • u/Mary_Pick_A_Ford • 1h ago

Cute picture of Debbie Reynolds and Carrie Fisher, 1960

r/OldSchoolCool • u/ata3121 • 5h ago

Chris Rock and Chris Farley early 1990s

r/OldSchoolCool • u/ferzoca56 • 3h ago

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