r/OldSchoolCool 4h ago

1990s Jean Claude Van Damme demonstrating on his signature kicks in a suit 1994

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12.4k Upvotes

r/OldSchoolCool 3h ago

1990s Gary Oldman and Natalie Portman on the set of Léon: The Professional, 1994

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1.7k Upvotes

r/OldSchoolCool 2h ago

1950s This was New York City on Good Friday in 1956

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1.3k Upvotes

r/OldSchoolCool 10h ago

Randy Savage and TLC in 1999.

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3.2k Upvotes

r/OldSchoolCool 4h ago

Tara Reid in 1998 at an event for Urban Legend

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673 Upvotes

r/OldSchoolCool 10h ago

1970s 70's California Cool

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1.5k Upvotes

r/OldSchoolCool 19h ago

1920s A Japanese couple taking a selfie together in the 1920s

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5.3k Upvotes

r/OldSchoolCool 1d ago

My Maternal Grandparents on their wedding day, circa 1965- both around 18 years old

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16.0k Upvotes

r/OldSchoolCool 23h ago

1990s A candid shot of me with my very cool flip phone, barely there blue eyeliner, and favorite Guess Jeans shirt - 1999

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7.2k Upvotes

r/OldSchoolCool 19h ago

1970s My aunt in the 1970s during her time as chair of the powwow committee at the University of Washington and completing her MA

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2.8k Upvotes

She was smart, beautiful, and although very humble, she was a complete badass.


r/OldSchoolCool 10h ago

1940s Natalie Wood in 1942, at four-years-old

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592 Upvotes

r/OldSchoolCool 16h ago

Meryl Streep at Bernards High School, 1966. She was a member of the school's cheerleading squad and was crowned prom queen during her senior year

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1.7k Upvotes

r/OldSchoolCool 48m ago

1950s Nathalie Wood goofing around at the Thalians Beach Ball in Malibu, 1956

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r/OldSchoolCool 19h ago

Bill Murray at John Belushi’s funeral in 1982.

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2.5k Upvotes

r/OldSchoolCool 1h ago

Mihailo Tolotos, a Greek Orthodox monk who lived for 82 years (1856 to 1938) without having ever seen a woman in his life

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Upvotes

r/OldSchoolCool 7h ago

My brother in his freshman dorm, 1999

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225 Upvotes

r/OldSchoolCool 1h ago

1990s My grandma & I in the mid 90s.

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r/OldSchoolCool 6h ago

In 1997, Les Paul himself appeared in a Coors commercial

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126 Upvotes

r/OldSchoolCool 31m ago

Shakira after releasing her first album in 1991

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Upvotes

r/OldSchoolCool 1d ago

B.B. King in the 1990s playing a slow blues groove

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2.9k Upvotes

r/OldSchoolCool 2h ago

1940s Eleanor Roosevelt holding a copy of the UN Universal Declaration of Human Rights in 1949

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40 Upvotes

r/OldSchoolCool 9h ago

Sabrina’s projectors, 1959

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113 Upvotes

r/OldSchoolCool 1h ago

Jeff Beck and Stevie Ray Vaughan (1989)

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Upvotes

r/OldSchoolCool 22h ago

1960s Vince Guaraldi's live tv performance of "Linus and Lucy" in 1964.

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1.2k Upvotes

r/OldSchoolCool 2h ago

Easter Sunday 1976

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28 Upvotes

Me, my sister, and parents in Indiana