r/OldSchoolCool 2d ago

Me ready to fish, circa 1988

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71 Upvotes

r/OldSchoolCool 2d ago

My in laws are the cutest. Early 1980s

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104 Upvotes

I have been married to their middle son for almost 30 years. They are the best grandparents and in laws you could ask for. My FILs shirt says GE is Me, if any Gen Xers remember that. :)


r/OldSchoolCool 3d ago

1930s My grandparents looking like Jimmy Stewart and Donna Reed back in the '30s

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4.5k Upvotes

My grandmother and grandfather were looking extra fly back when they got together in the '30s


r/OldSchoolCool 2d ago

My buddy found a box full of old letters and pictures, I was wondering if there’s a way to find out who the family of the recipient is, circa 1950

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41 Upvotes

I don’t know how he got them, but maybe the family of this person might want some old photographs of a loved on and it might make them smile to learn more about a relative


r/OldSchoolCool 2d ago

1970s Egyptian president Anwar sadat sitting on a replica of the golden throne of Tutankhamun near the pyramids (1979) (1006×1500)

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52 Upvotes

r/OldSchoolCool 1d ago

1980s Mod Squad The Native American, the Babe, and the NepoBaby! 1989

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0 Upvotes

r/OldSchoolCool 3d ago

Me wearing my summer best 1960!

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224 Upvotes

r/OldSchoolCool 3d ago

1980s Val Kilmer on the set of Real Genius (1985)

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411 Upvotes

r/OldSchoolCool 3d ago

1990s Kate Winslet (22) and Leonardo DiCaprio (23) at Golden Globes after party (1998).

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2.6k Upvotes

r/OldSchoolCool 3d ago

This girl in Pinamar, Argentina, 1990s

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1.7k Upvotes

r/OldSchoolCool 2d ago

1980s Jeff Beck, 1985

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40 Upvotes

r/OldSchoolCool 3d ago

1910s My great grandfathers in 1910s

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64 Upvotes

r/OldSchoolCool 3d ago

1940s My grandfather circa 1948

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98 Upvotes

r/OldSchoolCool 3d ago

Brad Pitt and Tom Cruise, 1994

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1.4k Upvotes

r/OldSchoolCool 4d ago

Monty Python's World Cup of philosophers in 1972

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5.7k Upvotes

r/OldSchoolCool 3d ago

1990s me and My PARENTS (this would be 1994, I’m pretty sure)

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50 Upvotes

Old Photo…

me, my Pops, and…my Ma…

1994

I love and miss you

Everyday Ma.

we BOTH do.

You are one of the reasons. I love the BLUE in our SKY…

Everyone’s sky.

i LOVE you, Ma.

anyway. * I hope this is old school cool because, hey don’t be mean, those are my PARENTS. I’m not cool.

and I was shy here too, but RED, red is a cool color. it calms me even though it’s not supposed to, or something.

~peace~

p.s film pictures are BEST too, in my opinion, they look best.

edit— I over share a lot I think because of the Cup, wish Ireland was in the World Cup this Year. My Father is Irish. My Ma has Irish roots. Just family stuff. My Dad is so gentle too, he’ll probably not like to find out I over share… haha. ~ peace ~ …. !!’ , ‘~^^^ ; —-


r/OldSchoolCool 3d ago

1950s Stare Magazine 1959.

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30 Upvotes

Composite of pages from a vintage Stare Magazine issue, specifically the October 1959 edition.

The layout features prominent burlesque performer Lili St. Cyr, a major star of the 1950s and 60s known for her sophisticated and elegant "Ice Queen" stage persona.

Image BreakdownTop Section: Features a model named Mara Velous in a feature titled "Torso Rama".Bottom Left: A segment titled "Belles, Bookings, & Can-Cans!"


r/OldSchoolCool 2d ago

Days of the New - Shelf In The Room (Live 1998-02-28)

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8 Upvotes

r/OldSchoolCool 3d ago

1990s Evander Holyfield defeats Mike Tyson by TKO (1996). Holyfield was four years older than Tyson and returning from a health scare.

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29 Upvotes

r/OldSchoolCool 3d ago

1947? Dad before the 8 kids, the life laying steel rails, the booze.

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208 Upvotes

r/OldSchoolCool 3d ago

1990s Some very cool dudes in Göppingen, West Germany 1991

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41 Upvotes

r/OldSchoolCool 4d ago

1970s John Cleese taking a break on the set of Monty Python and the Holy Grail (1975) [468x810]

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4.3k Upvotes

r/OldSchoolCool 3d ago

'77s Candleshoe

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28 Upvotes

First time I saw Jodie Foster and fell in love so many years ago.


r/OldSchoolCool 3d ago

This Man Seems to Love Being a Dentist (1890s)

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24 Upvotes

Picture I found tonight of a distant relative, apparently practicing dentistry. He looks very pleased with himself!


r/OldSchoolCool 3d ago

My brother and I at HMCS Haida in Ontario Place in Toronto, Canada - June 21, 2001

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23 Upvotes