My movie star looking grandparents sitting for a portrait in the early 1940s. (i.imgur.com)

1332 37 comments its_not_appropriate r/OldSchoolCool

A then-unknown 18y.o. Mariah Carey meeting Will Smith at a radio concert in 1988 (i.imgur.com)

12437 549 comments kevinlim512 r/OldSchoolCool

U.S. Marines driving through burning oil fields in Kuwait, 1991. (i.imgur.com)

27564 1234 comments deathakissaway r/OldSchoolCool

My grandma chilling with Muhammad Ali in Puerto Rico in the early 1970s (i.redd.it)

7143 56 comments Maddiekathleen r/OldSchoolCool

Early 1990's, Russia (i.redd.it)

6454 202 comments DCCXXVIII r/OldSchoolCool

My grandmother at 18 in Michoacan, Mexico-1945 (i.redd.it)

3689 72 comments chlorentine r/OldSchoolCool

My grandpa in front of the largest display of Clorox. 1965. (i.redd.it)

91 17 comments Blackout5154 r/OldSchoolCool

Elon Musk when attending Queen's University, 1990-1992 (i.redd.it)

4711 168 comments PoliQU r/OldSchoolCool

Jenna Fischer while working in fast food restaraunt in the 80s (shared.com)

10654 254 comments Riccardo91 r/OldSchoolCool

A young Bob Ross during his career in the Air Force circa 1960 (i.redd.it)

79 4 comments oakwimble r/OldSchoolCool

Benny Hill, Make a wish, 1960s. (i.imgur.com)

59 1 comments deathakissaway r/OldSchoolCool

Two of my great-uncles in the 40’s (i.redd.it)

34 6 comments nietsllah r/OldSchoolCool

My dad on the left wearing the trend of his time.. early 1980s (i.redd.it)

60 8 comments Mantequilla_Stotch r/OldSchoolCool

Child goes to say bye to his dad before his dad goes war. (1940’s WWII) (i.redd.it)

324 28 comments AriesPassionXX r/OldSchoolCool

My dad, sister, and mother on student residences at Karazin University, Kharkiv, USSR (1978) (i.redd.it)

21319 738 comments blaqrushin r/OldSchoolCool

A Korean-American civilian engaged in a shootout with drive-by shooters or snipers as he defended his grocery market during the 1992 Los Angeles riots, April 30, 1992 (i.redd.it)

25 7 comments TrendWarrior101 r/OldSchoolCool

Last photo of The Beatles together, August 22, 1969 (i.redd.it)

32 11 comments Churly10 r/OldSchoolCool

Two waiters serve two steel workers lunch while building the Waldorf-Astoria Hotel on Park Avenue in NYC, 1930 (i.redd.it)

7823 160 comments batmanbutawesome r/OldSchoolCool

My uncle chillin' with his pals in San Quentin, 1970 (i.imgur.com)

43 13 comments le_Francis r/OldSchoolCool

Frank Zappa and his cat Marshmoff, 1987 (i.redd.it)

32 1 comments dittidot r/OldSchoolCool

My grandmother in German occupied Paris during the 1940s. Note the soldiers in the background. (imgur.com)

25 2 comments Czarvana r/OldSchoolCool

Iron Mike Tyson 1975 (age 9) (imgur.com)

24 6 comments Sh1fty3yedD0g r/OldSchoolCool

Mom holding dad and my older sister, 1987. (i.redd.it)

3335 69 comments AstrologicalSin r/OldSchoolCool

My dad (age 4) and his father in 1970 (i.redd.it)

29 1 comments cloudpulp r/OldSchoolCool

Gothenburg, Sweden. 1966. (i.redd.it)

55 7 comments mjomark r/OldSchoolCool

My parents on their honeymoon, 1987. (imgur.com)

42 12 comments kittykween611 r/OldSchoolCool

Vivien Leigh during production of Victor Fleming’s “Gone with the Wind” (1939) (i.redd.it)

19 1 comments RainbowCloud5 r/OldSchoolCool

My grandmother modeling a necklace and earrings - 1976 (i.redd.it)

90 5 comments ianccoco r/OldSchoolCool

Marilyn Monroe with mandolin, Los Angeles, 1953 (i.imgur.com)

27 2 comments notbob1959 r/OldSchoolCool

Kurt Cobain and Dave Grohl - New York 1993 (i.redd.it)

30 2 comments RipplingShore r/OldSchoolCool

Legendary Ford Bronco 1994 (i.redd.it)

13 2 comments bilbodoyle96 r/OldSchoolCool

The cast of Reservoir Dogs, 1992 (i.redd.it)

21 0 comments nedelbach r/OldSchoolCool

Well, cool off pilgrim. John Wayne, 1959 (i.redd.it)

39 12 comments 305FUN r/OldSchoolCool

Sgt. Leslie Caraway from Nixon, Texas, stops along a trail for a rest and a cigarette, North of Pracchia, Italy. 7 December 1944. (Colorized) (i.redd.it)

9 1 comments rwwhite20 r/OldSchoolCool

My Grandpa drinking a beer and petting his dog, circa 1945 (i.redd.it)

19 1 comments jozimmer r/OldSchoolCool

An ad for aftermarket seatbelt installation from Chevron (Life Magazine, May 1963) (i.imgur.com)

26 1 comments Recursi r/OldSchoolCool

Justine Bateman (Mallory from Family Ties), 1982. (i.pinimg.com)

129 16 comments WorkTomorrow r/OldSchoolCool

Olivia Hussey late 60’s (i.redd.it)

15 1 comments sresendes73 r/OldSchoolCool

The Wilson sisters (Ann and Nancy) of Heart. [1970's] (i.redd.it)

9 1 comments justatheery r/OldSchoolCool

My dad David Brenner boxing a kangaroo on The Mike Douglas Show, 1978 (i.redd.it)

12 4 comments umiland r/OldSchoolCool

My grandfather testing out his new pistol 1947 (i.redd.it)

12 0 comments Fine_bobby r/OldSchoolCool

Two Polish Boys Reading Mickey Mouse, Warsaw, 1939 (commons.wikimedia.org)

8 0 comments ringoandgibby r/OldSchoolCool

The Jordache Look, 1984. Yikes. (youtu.be)

11 8 comments ConsumerTimeCapsule r/OldSchoolCool

My grandmother (left) and her best friend ca. 1955-always thought they evoked “coolness” in this photo (i.redd.it)

7 2 comments FatsyCline12 r/OldSchoolCool

Kate Hudson posing with her mother Goldie Hawn and their dog in 1996 for InStyle. I really love those "famous child with famous parent"-photos. (i.imgur.com)

12 1 comments I-ate-your-pony r/OldSchoolCool

My paternal grandfather at a high school dance (late 60s or early 70s) (i.imgur.com)

8 3 comments AvuncularPederast r/OldSchoolCool

I see your early 90’s Russia, and raise you early 90’s Canada (i.imgur.com)

108 11 comments Michellehas2ls r/OldSchoolCool

This is the original 1920's control panel at the power station that generated all the electricity for the London underground tube (subway) system. (i.redd.it)

6 1 comments Hidethegoodbiscuits r/OldSchoolCool

Jupiter, FL Lighthouse - 1891 (i.imgur.com)

14 0 comments JupiterUnleashed r/OldSchoolCool

My great grandparents and kin to The Bell Witch of Tennessee. Nannie and Pap Bell. (April 1970) (i.redd.it)

6 0 comments SilentWalrus92 r/OldSchoolCool

French Nun, circa 1900. (i.redd.it)

16 2 comments thebeanpole16 r/OldSchoolCool

My grandpa, then boxing commissioner of Minnesota (back right in blue), w Muhammad Ali and company. 1970s (i.redd.it)

11 2 comments lil_doopy_doop r/OldSchoolCool

My grandmother at 2 in 1922 (i.redd.it)

6 0 comments mangosplumsgrapes r/OldSchoolCool

Kate Chase Sprague, best known as a society hostess during the Civil War, 1860 (i.imgur.com)

9 2 comments RyanSmith r/OldSchoolCool

Captain Bruce Ballantyne, Patrol commander of T Patrol, the Long Range Desert Group (LRDG), probably taken in the Western Desert, Libya, 1940-43 (i.redd.it)

24 0 comments therunawaychain r/OldSchoolCool

Virginia Bell, 1950s (ist3-1.filesor.com)

154 30 comments joeclark5 r/OldSchoolCool

This is my Grandpops teaching students in Andrew Jackson High School Queens NY in 1959. (i.redd.it)

4 2 comments thisboyhasverizon r/OldSchoolCool

Me and my Ironhead Sportster circa 1990. (i.redd.it)

17 3 comments DJThruxton r/OldSchoolCool

Burlesque Performer, Barbara Yung, 1940's. (i.redd.it)

41 0 comments bbambzi r/OldSchoolCool

Churchill and Eisenhower overseeing a drill in my grandad's farmland-1943 (i.redd.it)

22 2 comments king12435 r/OldSchoolCool

My photographer dad and my mum testing the lighting for a shoot mid 80s (i.redd.it)

818 30 comments ArtturPonde r/OldSchoolCool

East German soldier helping a boy cross the new Berlin Wall, to reunite with his family. 1961. (i.redd.it)

31946 775 comments codywinters327 r/OldSchoolCool

Verne Troyer's Prom Photo, 1980's (imgur.com)

178 6 comments a_bitch_on_a_mission r/OldSchoolCool

My grandmother in New York circa 1945 (i.redd.it)

57 2 comments mangosplumsgrapes r/OldSchoolCool

my mother, me and my grandmother around 1994. (i.redd.it)

10 0 comments WaterMelonE0001 r/OldSchoolCool

1951 - Vampire the cat, one of five similarly named cats my Grandfather had in his lifetime. He thought fierce names made animals brave and proud. Photo taken on the bank of the Ottawa River. (imgur.com)

39 2 comments sailwithgrace r/OldSchoolCool

(1930) My great grandfather at Highcliffe beach UK (i.imgur.com)

8 1 comments HeWhoCannotBeArsed r/OldSchoolCool

My Parents Shortly After Getting Married - 1960s (imgur.com)

3 0 comments PrettyPandaPrincess r/OldSchoolCool

R. Lee Ermey (aka Gunnery Sergeant Hartman) shining his boots while serving in the U.S. Marine Corp - 1961 (i.redd.it)

379 48 comments Dont_Jersey_Vermont r/OldSchoolCool

A musician carries his bass, 1961 [photo by Yomislav Peternek] (i.redd.it)

26 0 comments highcontrastgrey r/OldSchoolCool

Just watched Daisies(1966) Czech arthouse film, and fell in love with Jitka Cerhova. Anyone know any information about her? (i.redd.it)

4 0 comments barbarossa1973 r/OldSchoolCool

Uncle Larry, the ladies man. 1964 (i.redd.it)

2 0 comments derpywaffle24 r/OldSchoolCool

My dad hanging with his classic beauty in the 70's. (i.redd.it)

195 21 comments waroftyr r/OldSchoolCool

My grandparents young and in love in 1950's (i.redd.it)

2 0 comments Celetron r/OldSchoolCool

My uncles Johnny, Timothy, Maffa and Adam 1960's (i.redd.it)

104 6 comments dragonbornsqrl r/OldSchoolCool

In honor of my little sisters 32nd birthday today, here’s a pic of us from 1988. (i.redd.it)

2 0 comments LydierBear r/OldSchoolCool

I posted them on here a few weeks ago, but this one warms my heart more. My Gramma, Grandpa, Dad (the smartass), and Uncle in ~late 1970s. The horrible matching outfits and my grandfather's hair situation just push me over the edge. (i.redd.it)

34 9 comments andthenioverthought r/OldSchoolCool

Johnny Cash mugshot 1966 (i.redd.it)

50 4 comments K1nsey6 r/OldSchoolCool

It's a Major Award! Grandfather, a traveling salesman in the early 50s, receiving a watch for top sales. (Zippo Lighter sales we believe.) (i.redd.it)

32 7 comments mightydeez r/OldSchoolCool

James Brown teaching dance moves in the 1970s (youtube.com)

2 2 comments jcepiano r/OldSchoolCool

Quadricycle c.1894 (vergue.com)

32 1 comments highcontrastgrey r/OldSchoolCool

My great-great grandfather smoking a pipe while driving a convertible c.1930 (imgur.com)

2 0 comments dexterpine r/OldSchoolCool

My grandma when she was 16, 1976 (i.redd.it)

49 16 comments kaylacactus r/OldSchoolCool

My grandparents (January 1968) (i.redd.it)

51 5 comments SilentWalrus92 r/OldSchoolCool

Brigitte Bardot (1950s) (i.redd.it)

238 9 comments Bolinas99 r/OldSchoolCool

My grandparents; late 40s / early 50s. (i.redd.it)

17 1 comments god-of_tits-and_wine r/OldSchoolCool

Young George RR Martin circa 1972 (pbs.twimg.com)

3 6 comments iaxeuanswer r/OldSchoolCool

My grandfather’s family of illegal bookmakers in 1930s Coventry. My granddad at the front in the shorts, with my great granddad holding his hand. (i.redd.it)

12 9 comments IrvingWashington2322 r/OldSchoolCool

Helen Mirren - 1960's (i.redd.it)

191 23 comments Anton_Tobias r/OldSchoolCool

My grandfather (left) sparring in the early 60's (i.redd.it)

20 8 comments LetsGetBlaziken r/OldSchoolCool

William Hartnell (as Will Buckley) and Peter Sellers (as Tully Bascombe) in the movie "The Mouse That Roared" (1959) (i.redd.it)

18 0 comments SF_Dweller r/OldSchoolCool

My aunt with her cat, Brawny, in her pocket. Circa 1975 (i.redd.it)

19 2 comments dirtmop28 r/OldSchoolCool

One of the few pics I have of my grandpa. Approx. 1950 I believe. He was a Korean war vet, a farmer, and a house builder. (i.redd.it)

15 0 comments Deppfan16 r/OldSchoolCool

Another picture of my mother, on the left, as a nurse, Mexico July 25, 1970 (i.redd.it)

4099 65 comments princessfafa r/OldSchoolCool

The grandparents - RAF in Aden (1960's) (i.imgur.com)

6 0 comments Dannyguard r/OldSchoolCool

Vintage Harley 1904 (i.redd.it)

35 2 comments K1nsey6 r/OldSchoolCool

Grandmother in Cuba around the 1940s/50s (imgur.com)

20 2 comments birdieflo r/OldSchoolCool

My father on the USS Orion, mid 1950's (i.redd.it)

14 2 comments badtux99 r/OldSchoolCool

Dad Jumping His Boat, 1971 (i.imgur.com)

197 5 comments no_problemo r/OldSchoolCool

Betty White (1957) (i.redd.it)

1274 23 comments KinneyBoi r/OldSchoolCool