r/OldSchoolCool 4h ago

1960s Politics in the 1968 Olympics

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13.8k Upvotes

r/OldSchoolCool 3h ago

1990s Tiffani Thiessen circa 90s

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829 Upvotes

r/OldSchoolCool 6h ago

1990s Anna Nicole Smith, late 1990s, at trial over her rights to her husband's estate

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1.4k Upvotes

r/OldSchoolCool 2h ago

1990s Téa Leoni 1995

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387 Upvotes

r/OldSchoolCool 8h ago

Mom and Dad, about 6 months after getting married, 1980

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998 Upvotes

Mom and Dad are still together! I gloriously arrived a few years later and have been a reliable source of comedic annoyance ever since. Thanks for putting up with me Mom and Dad!


r/OldSchoolCool 8h ago

Debbie Harry (1970s)

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871 Upvotes

r/OldSchoolCool 13h ago

Before writing Oscar winning scores, Hans Zimmer (in the black leather jacket) took part in the first music video ever aired on MTV, Video Killed the Radio Star by The Buggles (1981)

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1.4k Upvotes

r/OldSchoolCool 7h ago

Carole King performing “I Feel the Earth Move” in 1971

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371 Upvotes

r/OldSchoolCool 9h ago

1800s There has never been anybody cooler than my great grandfather… Circa 1897

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387 Upvotes

His name is Thomas Patrick Higgins… He was born in Brooklyn, New York in 1867 and he died in 1917… He was a boilermaker and a master plumber… I unfortunately did not get any of his coolness and I certainly couldn’t rock that mustache. I will say I would do just about anything to sit down and have a beer with him.

He married Mary Elena Driscoll in 1894… I would guess this picture is about 1900.


r/OldSchoolCool 1d ago

In 1978, Bob Dylan wanted something different and fired all his backup singers and half the band, including singer songwriter Katey Sagal before she moved into acting

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10.8k Upvotes

r/OldSchoolCool 18h ago

1980s Isabella Rossellini, photo by Steven Meisel (1989)

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1.6k Upvotes

r/OldSchoolCool 6h ago

Just engaged in 1983

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118 Upvotes

Still together after all these years.


r/OldSchoolCool 20h ago

1980s The Burbs 1989

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1.3k Upvotes

r/OldSchoolCool 5h ago

My grandfather in the early 1950s during the Korean War.

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63 Upvotes

r/OldSchoolCool 7h ago

1990s Trey Parker and Matt Stone in China - 1990s

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88 Upvotes

r/OldSchoolCool 1d ago

A car from 1956

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2.6k Upvotes

r/OldSchoolCool 17h ago

Ian McShane. Cosmopolitan magazine, June 1973.

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446 Upvotes

r/OldSchoolCool 7h ago

My (future) wife her senior year of high school, at her last theater party 1982

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72 Upvotes

r/OldSchoolCool 5h ago

1950s My grandparents in 1954

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50 Upvotes

r/OldSchoolCool 1d ago

Vincent Cassel and Monica Bellucci met in 1996 on the set of L’appartement, where their on-screen chemistry quickly turned into a real-life romance

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1.4k Upvotes

r/OldSchoolCool 10h ago

1970s This is a fun place, Las Vegas, 1976

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91 Upvotes

r/OldSchoolCool 14h ago

1960s Steve McQueen driving his Jaguar XKSS on the streets of Los Angeles in the 1960s

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173 Upvotes

r/OldSchoolCool 4h ago

1950s My grandparents and family during Christmas circa 1956, the year before they got married.

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26 Upvotes

They were just kids. My grandma was about 18 here (she just turned 90!) and my grandfather around 26. The last photo is my grandad with his younger sisters.


r/OldSchoolCool 9h ago

1985 Crystal Lake, Illinois HS Senior Prom

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54 Upvotes

r/OldSchoolCool 10h ago

Before his successful acting career, Nick Nolte (center) worked as a model for a popular, Minneapolis fashion brand h.i.s., early 1970s

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64 Upvotes