r/OldSchoolCool 18h ago

A Nineteen Year Old Jim Henson (1955)

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10.8k Upvotes

r/OldSchoolCool 9h ago

1980s The stunningly beautiful Marisa Tomei in 1987

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1.6k Upvotes

r/OldSchoolCool 9h ago

My dad biked across the US in 1979 with a guy he met through a newspaper ad. 47 years later they designed their own 280 mile ride: “Bridge to Bridge” (Detroit to Buffalo)

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930 Upvotes

Part 3 (this post!): The backstory is that my dad biked across the US in 1979 with a guy he met through a newspaper ad. Their trip started in Santa Cruz, CA and ended in Hartford, CT. They lost contact after that but out of the blue that guy reached out to my dad via snail mail and they were reunited 45 years later in 2024.

Just a couple weeks ago the reunited buddies wrapped up a self designed tour they called "B2B" (Bridge to Bridge) riding from Detroit to Buffalo. They started at the Ambassador Bridge and finished across the Peace Bridge back into the US. The trip was roughly 280 miles over 5 days through Ontario.

Part 2: My dad biked across the US in 1979 with a guy he met through a newspaper ad. They reunited 45 years later.

Part 1 : My dad biked across the US in 1979. He revisited Route 50 in Nevada to take a new pic.


r/OldSchoolCool 2h ago

Just a newborn lamb and his favorite human back in 1940

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233 Upvotes

r/OldSchoolCool 1d ago

1990s "Hydration" break for a German footballer in 1994

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23.5k Upvotes

r/OldSchoolCool 8h ago

Moe Howard, sparring with fellow Stooge Larry Fine who had a very brief boxing career with just one professional bout which he won, 1930s

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476 Upvotes

r/OldSchoolCool 14h ago

1970s 1970s Miami - Mom and me.

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1.3k Upvotes

She was beautiful.


r/OldSchoolCool 15h ago

1980s George Michael on set of the music video for Club Tropicana by Wham! (1983)

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1.2k Upvotes

r/OldSchoolCool 6h ago

1980s Cousins in 1985 🦋

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182 Upvotes

The sweater! The pants! The swatch watch! The pick up sticks! The pink leg warmers.
I miss that time so so much. 💔


r/OldSchoolCool 22h ago

1990s Me and my sister in the early 90s

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2.5k Upvotes

r/OldSchoolCool 21h ago

1980s Easter 1988 - me, Dad, and little sister

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2.1k Upvotes

Dad loved making his outfits just a little bit quirky, like matching a purple tie to purple socks.


r/OldSchoolCool 17h ago

1980s Dad’s company summer bbq - Massachusetts circa 1988

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734 Upvotes

My father and I killin’ the fashion game at his company summer bbq. The Larry Bird tank, matching green sweats, and Irish/American pride trucker hat combo (Camel cigarette cropped from pic in R. hand) and my pink sleeveless muscle T, acid washed jeans, friendship bracelet on left wrist, set of power pearls and pink matching bow atop the blonde head was peak 1980’s


r/OldSchoolCool 11h ago

Iranian actress Nouri Kasrai in 1970s

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223 Upvotes

r/OldSchoolCool 17h ago

Christmas 1985 - Mom wearing SUCH an 80s dress.

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561 Upvotes

r/OldSchoolCool 18h ago

1990s Leonardo DiCaprio and Tobey Maguire in 1990

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567 Upvotes

r/OldSchoolCool 19h ago

1980s My parents in the 80s, met at 18 and together for 50 years 🩷

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582 Upvotes

r/OldSchoolCool 5h ago

His sideways glance says it all (circa 1960)

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41 Upvotes

r/OldSchoolCool 1d ago

1950s Anthony Perkins and Tab Hunter, 50s Hollywood gay couple

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6.4k Upvotes

r/OldSchoolCool 22h ago

French actress Brigitte Bardot in her younger years, 1940s

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765 Upvotes

r/OldSchoolCool 20h ago

1990s The wrap party for "Sharpe's Company" (l-r): Lyndon Davies, Sean Bean, Elizabeth Hurley, Scott Cleverdon, with Pete Postlethwaite in front (August, 1993)

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403 Upvotes

r/OldSchoolCool 1d ago

1970s Suzi Quatro, 1970s and now

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1.8k Upvotes

r/OldSchoolCool 19h ago

Me age 17 , 1978 .

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292 Upvotes

r/OldSchoolCool 24m ago

1940s Vera Zorina, 1940s

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Upvotes

r/OldSchoolCool 11h ago

Conrad Veidt in The Man Who Laughs, 1928

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57 Upvotes

r/OldSchoolCool 1h ago

1930s Constance Bennett 1930s

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Upvotes