Old School Cool

Credit to the original poster Kev45ert who posted this on r/OldSchoolCool on December 8th, 2025 at 12:50 AM UTC.

Groucho and Marylin mid-1950's

Credit to the original poster Imdevilone who posted this on r/OldSchoolCool on December 8th, 2025 at 12:31 AM UTC.

Me with Chuck E. Cheese for my 6th birthday in 1988.

Credit to the original poster Ok-Story-3532 who posted this on r/OldSchoolCool on December 8th, 2025 at 12:26 AM UTC.

1983 (i think): My Newfie Grandfather smoking a cigarette, pulling a fish out of the water with both hands, in a canoe.

Credit to the original poster Eaglemaxie who posted this on r/OldSchoolCool on December 8th, 2025 at 12:22 AM UTC.

Credit to the original poster Eaglemaxie who posted this on r/OldSchoolCool on December 8th, 2025 at 12:22 AM UTC.

Writer, director, producer, and star of 'The Great Dictator' Charlie Chaplin’s masterful anti-fascist satire began filming in 1939, right at the start of World War II

She gave a very brave performance in the movie "lifeforce". Credit to the original poster Greggers1980 who posted this on r/OldSchoolCool on December 8th, 2025 at 12:07 AM UTC.

Mathilda may. Lifeforce 1985

Credit to the original poster Wild_Panda873 who posted this on r/OldSchoolCool on December 8th, 2025 at 12:03 AM UTC.

My family in the 70's

Credit to the original poster Rockstoned4 who posted this on r/OldSchoolCool on December 7th, 2025 at 11:48 PM UTC.

Tiffani Amber Thiessen in the early 90s.

Credit to the original poster Vsully360 who posted this on r/OldSchoolCool on December 7th, 2025 at 11:42 PM UTC.

First grade in spring of 1983. That’s me in the upper right with a striped shirt.

Credit to the original poster Alone_Confidence_158 who posted this on r/OldSchoolCool on December 7th, 2025 at 11:25 PM UTC.

Just another day in the 80's. Hanging out at the mall.

Posing with his first car Credit to the original poster Iloafyoualot who posted this on r/OldSchoolCool on December 7th, 2025 at 11:21 PM UTC.

Dad in the 40s

Credit to the original poster Majestic_Relief_9431 who posted this on r/OldSchoolCool on December 7th, 2025 at 11:04 PM UTC.

Bruce Lee (1973)

Credit to the original poster Mad_Season_1994 who posted this on r/OldSchoolCool on December 7th, 2025 at 10:54 PM UTC.

In 1997, Daft Punk would release a song where three words are repeated over and over...and it would go on to become one of their biggest hits

Me and my cousin on our first bikes! Credit to the original poster Present_Most1479 who posted this on r/OldSchoolCool on December 7th, 2025 at 10:17 PM UTC.

Me and my cousin on our first bikes! Credit to the original poster Present_Most1479 who posted this on r/OldSchoolCool on December 7th, 2025 at 10:17 PM UTC.

My dad and uncle on their first bikes!!! #Badass circa 1987

yeah, i did a double-take too when i saw it in the box of old photos 😂 Credit to the original poster Okay-flight who posted this on r/OldSchoolCool on December 7th, 2025 at 9:33 PM UTC.

yeah, i did a double-take too when i saw it in the box of old photos 😂 Credit to the original poster Okay-flight who posted this on r/OldSchoolCool on December 7th, 2025 at 9:33 PM UTC.

My absolute destruction of a Ninja Turtles squeeze treat, summer 1994

Credit to the original poster PourSomeSugar69_420 who posted this on r/OldSchoolCool on December 7th, 2025 at 9:04 PM UTC.

Cher (1966)

Photo by Daily Mirror photographer Hy Peskin. Fascinating view into the news release of the attack on Pearl Harbor 84 years ago as of today. Not a repost, this is an original scan. Credit to the original poster PortraitsofWar who posted this on r/OldSchoolCool on December 7th, 2025 at 8:59 PM UTC.

Photo by Daily Mirror photographer Hy Peskin. Fascinating view into the news release of the attack on Pearl Harbor 84 years ago as of today. Not a repost, this is an original scan. Credit to the original poster PortraitsofWar who posted this on r/OldSchoolCool on December 7th, 2025 at 8:59 PM UTC.

Photo by Daily Mirror photographer Hy Peskin. Fascinating view into the news release of the attack on Pearl Harbor 84 years ago as of today. Not a repost, this is an original scan. Credit to the original poster PortraitsofWar who posted this on r/OldSchoolCool on December 7th, 2025 at 8:59 PM UTC.

Photo by Daily Mirror photographer Hy Peskin. Fascinating view into the news release of the attack on Pearl Harbor 84 years ago as of today. Not a repost, this is an original scan. Credit to the original poster PortraitsofWar who posted this on r/OldSchoolCool on December 7th, 2025 at 8:59 PM UTC.

The Morning of December 7th, 1941, News Reporters Learn of the attack on Pearl Harbor

Credit to the original poster USRoute23 who posted this on r/OldSchoolCool on December 7th, 2025 at 8:48 PM UTC.

Kristy McNichol 1984

Credit to the original poster Mightywellfan who posted this on r/OldSchoolCool on December 7th, 2025 at 8:16 PM UTC.

Bay City Rollers fans outside Apollo theatre Glasgow April 1975

Credit to the original poster Sprinkill who posted this on r/OldSchoolCool on December 7th, 2025 at 8:02 PM UTC.

Bon Scott, lead singer of AC/DC, 1977

Credit to the original poster Mohtarefnadafa who posted this on r/OldSchoolCool on December 7th, 2025 at 7:58 PM UTC.

Marilyn Monroe Performing for the Thousands of American Troops in Korea, 1954

Credit to the original poster Harleybug88 who posted this on r/OldSchoolCool on December 7th, 2025 at 7:48 PM UTC.

Old school football, 1960's

Credit to the original poster Maximum_Expert92 who posted this on r/OldSchoolCool on December 7th, 2025 at 7:43 PM UTC.

Jennifer Jason Leigh before Broadway debut in Cabaret (1998)

Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on December 7th, 2025 at 7:17 PM UTC.

Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on December 7th, 2025 at 7:17 PM UTC.

Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on December 7th, 2025 at 7:17 PM UTC.

Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on December 7th, 2025 at 7:17 PM UTC.

Michael J. Fox in 1985

Credit to the original poster Agfacid1 who posted this on r/OldSchoolCool on December 7th, 2025 at 7:08 PM UTC.

Mythical burglar from the 60s

Credit to the original poster BabyPrincesssxo who posted this on r/OldSchoolCool on December 7th, 2025 at 6:35 PM UTC.

I was in march 1998 issue #177 of EasyRiders magazine. Picture taken by the Mad Doctor in February 1987. I was 20 yes old

Alain Delon at Cannes Film Festival 1957 before he became a star - where he was discovered by Henry Willson, David O. Selznick's talent scout - but in 1957, he was a nobody, just the boyfriend of actress Brigitte Auber, living in her house in Saint-Paul-de-Vence, and thanks to her, being to able to watch some of the movies at the Festival... Credit to the original poster Major_MKusanagi who posted this on r/OldSchoolCool on December 7th, 2025 at 6:01 PM UTC.

Alain Delon in Cannes 1957

Credit to the original poster L0st_in_the_Stars who posted this on r/OldSchoolCool on December 7th, 2025 at 5:41 PM UTC.

Charles Schulz with the beagle who was the model for Snoopy, 1950s.

Credit to the original poster Jeetchat who posted this on r/OldSchoolCool on December 7th, 2025 at 4:58 PM UTC.

The British Army in Burma 1945 - An infantryman shaving in his slit trench, April 12 1945.

Credit to the original poster Substantial-Pipe4400 who posted this on r/OldSchoolCool on December 7th, 2025 at 4:39 PM UTC.

1985 trailer park family

Text: A photo of my Great Great Grandparents in the mid-1870s. He lived until 1880. She passed on 1903. They had 11 children. Photo probably taken in Pickens or Lamar County, Alabama. Credit to the original poster CarrierCaveman who posted this on r/OldSchoolCool on December 7th, 2025 at 4:14 PM UTC.

Great Great Grandparents (1875)