Leonardo DiCaprio and Shalom Harlow at a dinner party thrown by Gianni Versace, 19952wk ⋅ haloarh ⋅ r/OldSchoolCool
My father (forth from the left in green tee and white suspenders) and his band mates posing for a photo shoot in Denver, Colorado. I’m pretty sure this was 1977. The band’s name was “Orphan Annie” and they played the bar/club scene in the mid to late 70’s.2yr ⋅ Negrodamus1991 ⋅ r/OldSchoolCool
My grandma (front) and my great aunt looking cool in 1965, colorized by me.4yr ⋅ ayanoyamada ⋅ r/OldSchoolCool
My grandmother in 1935 when she was 14 years old. She was a working woman and mother her entire adult life. She was once the fastest typist (on a typewriter) in the state of Utah. When she was 90, I recorded a video of her dancing to Part Rock Anthem, which went viral in 2012. What a life.3yr ⋅ SoggyOil ⋅ r/OldSchoolCool
In 2012 I came home one day with a new motorcycle, nobody in my family was happy about it except for my Nonna which was suprising. Not long after she dug up this picture of her in Italy shortly after ww2.4yr ⋅ puggernault ⋅ r/OldSchoolCool
My grandmother was a code girl during WWII. It was her best kept secret until 2017.4yr ⋅ Aek2332 ⋅ r/OldSchoolCool
My son and I in the early 90s. We couldn‘t afford a camera, so we periodically went into a photobooth.5yr ⋅ askalottle ⋅ r/OldSchoolCool
My father-in-law drove a big rig with his face painted on the side -- 1970s3yr ⋅ wondrouswalnut ⋅ r/OldSchoolCool
Astronaut Bruce McCandless II spacewalk without a safety tether linked to a spacecraft. 19846mo ⋅ quegrawks ⋅ r/OldSchoolCool
A member of the 369th Infantry Regiment (aka Harlem Hellfighters) holds a puppy that he saved during World War I (1918)4yr ⋅ WhileFalseRepeat ⋅ r/OldSchoolCool
Ben Affleck and Matt Damon wearing matching puka necklaces, aged 16 and 15. (1980s)8mo ⋅ mikeyypeng ⋅ r/OldSchoolCool
Lenny Bruce being arrested for obscenity and George Carlin being arrested for refusing to show his ID to the police at the same show, 5 December 19622yr ⋅ Tbot6000 ⋅ r/OldSchoolCool
My great grandmother and her friends Roman and Sharon in late 1960s9mo ⋅ SkinnyJoshPeck ⋅ r/OldSchoolCool
John Madden yelling at referee (1970). RIP to the great John Madden.2yr ⋅ YoureASkyscraper ⋅ r/OldSchoolCool
French woman pouring tea for a British soldier fighting in Normandy 19444yr ⋅ onepersononeidea ⋅ r/OldSchoolCool
The slide at recess just hit different back in the 70's and 80's.1yr ⋅ Cemeterywind666 ⋅ r/OldSchoolCool
On this day 79 years ago my great uncle Captain Joseph T Dawson led the first wave of soldiers onto Omaha Beach during D-Day. This is him being awarded the Distinguished Service Cross by General Eisenhower afterwards.11mo ⋅ Okaynowwatt ⋅ r/OldSchoolCool
Stealing a drink of wine at a wedding while my mom (behind me) isn’t looking. (1987)4yr ⋅ lanko69 ⋅ r/OldSchoolCool
Christina Applegate and Brad Pitt, Pitt was her date to the 1989 MTV Movie Awards... until she ditched him for another guy.9mo ⋅ DaddiesLittleBottom ⋅ r/OldSchoolCool
Jackie & Kelso from “That 70’s Show” remind me of my parents. Here they are on their honeymoon. (1972)4yr ⋅ bdarps ⋅ r/OldSchoolCool
In 1965 Dervla Murphy journeyed alone from her native Ireland to India on a bicycle, armed with little more than a pistol, a notebook and a compass. Dervla died last month, aged 902yr ⋅ YtjmU ⋅ r/OldSchoolCool
Christmas morning 30 years ago, when my brother and I received a NES (1990)3yr ⋅ tiretpointunderscore ⋅ r/OldSchoolCool
Suffragette showing off her pants in 1916 (considered immoral at the time)1yr ⋅ moviebuffman ⋅ r/OldSchoolCool
Anti-fascist folk singer Woodie Guthrie, writer of This Land Is Your Land, circa 19431yr ⋅ frustrating2020 ⋅ r/OldSchoolCool
Me and the homies before going to see Straight Outta Compton. The tour, not the movie. Circa 19895yr ⋅ iaintsaidshit ⋅ r/OldSchoolCool
My great grandfather holding my great uncle a hundred years ago in 1919.5yr ⋅ Chopperguy ⋅ r/OldSchoolCool
These students were suspended for protesting the Vietnam War. They brought it all the way to the supreme court and won. (1968)2yr ⋅ M_Faisal ⋅ r/OldSchoolCool
1976. It was a very good year for a pink polyester tuxedo with my larger than life Afro.4yr ⋅ 19266042 ⋅ r/OldSchoolCool
My wife and I at the start of our first summer trip out to the West Coast together in 1985 from Minneapolis. Camped in a tent. Currently, living in a van 8 months a year. Still having the time of our lives...3yr ⋅ HighlanderTCBO1 ⋅ r/OldSchoolCool
1985 & 2019. It's all I wanted for my 60th birthday (x-post /R/PastAndPresentPics)5yr ⋅ madbear ⋅ r/OldSchoolCool
[1996] A random man picked me up on a street in Arkansas and put me on his pet bear. It attacked a lady moments later.1yr ⋅ WeHaveAllBeenThere ⋅ r/OldSchoolCool
Windows on the World, restaurant on top of the former World Trade Center, 1980s4yr ⋅ earthmoonsun ⋅ r/OldSchoolCool
It’s my birthday today; here I am at the peak of my coolness, in 1984, hosting my first party in my first apartment.4yr ⋅ twodaisies ⋅ r/OldSchoolCool
Slash in 1982 before Guns N’ Roses was started, and he was known as Saul!4yr ⋅ Walusqueegee ⋅ r/OldSchoolCool
My mom getting ready for prom. Grandma didn’t like my dad, can you tell? 1970s2yr ⋅ jesscubby ⋅ r/OldSchoolCool
Anthony Hopkins and Jodie Foster holding their Oscars for Best Actor and Best Actress, 1992. They both won for their performances in the movie The Silence of the Lambs.2yr ⋅ pegasustoonkingdom ⋅ r/OldSchoolCool
My mother in 4th grade in the 70s. Her mother wouldn't let her bring the outfit for picture day so she brought it with her and changed at school. A patchwork cowboy shirt, a bandana and a velvet Pakistani vest.3yr ⋅ remember_8 ⋅ r/OldSchoolCool
Yul Brynner in 1956 arriving to the premiere of The Ten Commandments in his Mercedes-Benz 300SL Roadster1yr ⋅ Mad_Season_1994 ⋅ r/OldSchoolCool
Civil Air Patrol student pilot, Silver Lake airfield near Baker, California, 19443yr ⋅ notbob1959 ⋅ r/OldSchoolCool
Prince or Michael Jackson: Which one was your favorite? (1980s)9mo ⋅ Precocious_Pussycat ⋅ r/OldSchoolCool
1969, Chris Noel with American Troops in Vietnam. She went 8 times, was so popular the enemy placed $10k bounty on her and twice her helicopter was shot down by enemy fire.1yr ⋅ Luckygecko1 ⋅ r/OldSchoolCool
My grandma, Mary Jane, during WWII while working at the Department of Agriculture.1yr ⋅ ktazhsv ⋅ r/OldSchoolCool
Kurt Cobain drinking strawberry nesquik in the flat of then girlfriend Tracy Marander, 1989. He believed it helped his stomach pains2mo ⋅ puntelbalkings85 ⋅ r/OldSchoolCool
She will be missed greatly. Betty White on her sixth birthday, 1928.2yr ⋅ Paul-Belgium ⋅ r/OldSchoolCool
Stephen King opens the gates to his new Victorian-style house, guarded by bats. November 198211mo ⋅ DinhaMidzy ⋅ r/OldSchoolCool
Pamela Anderson, photographed on the set of sitcom Home Improvement, 19912yr ⋅ Turd_Burglerson ⋅ r/OldSchoolCool
My weight lifter great grandpa holding my grandpa over his head - 19475yr ⋅ brentgolding ⋅ r/OldSchoolCool
1977 - Mark Hamill and Carrie Fisher - Now that's some old school cool right there...3yr ⋅ Karness_Muur ⋅ r/OldSchoolCool
My grandma and grandpa shortly after getting married and moving to LA in 19653yr ⋅ jurkid ⋅ r/OldSchoolCool
Mr. and Mrs. Emory Harrison of Jonesboro, Tenn., had 13 children, all boys, making the largest all-male American family in 19551yr ⋅ newleafkratom ⋅ r/OldSchoolCool
Farmers “arrest” the sheriff for trying to evict a woman from her farm on behalf of the insurance company. Michigan, 1952.3yr ⋅ CSA1935 ⋅ r/OldSchoolCool
