1966 - Dolly Parton in a photo booth at 20 years old3d ⋅ LoudRevolution9163 ⋅ r/OldSchoolCool ⋅ #1966 #20
She was the first Chinese American woman to earn a pilot's license in 1932 at the age of 20 🛩️May 22 ⋅ Sno0pyBo0 ⋅ r/OldSchoolCool ⋅ #WASP #1932 #20
Billy Idol (27) and Demi Moore (20) in the backstage 1982.Jul 2025 ⋅ EmmyEchos ⋅ r/OldSchoolCool ⋅ #20 #27
20 year old Dolly Parton in a recording studio, 1966Nov 2024 ⋅ Alternative_Act_1578 ⋅ r/OldSchoolCool ⋅ #1966 #20
Before becoming a Brigadier general, Stewart flew 20 official combat missions in B-24 Liberator bombersAug 2 ⋅ eaglemaxie ⋅ r/OldSchoolCool ⋅ #20 #24
My great uncle who was posthumously awarded for killing 20 Nazis and destroying a tank, as well as twoSep 2024 ⋅ Wheresmywilltoliveat ⋅ r/OldSchoolCool ⋅ #20
My grandmother was too short to model, so she wound up modeling hats and jewelry when she was in her 20s.Aug 2021 ⋅ DizzyUpThaGirl ⋅ r/OldSchoolCool ⋅ #20
My grandma (20) and grandpa (22), sometime in the 50sDec 2023 ⋅ cynical_Rad359 ⋅ r/OldSchoolCool ⋅ #20 #22
My 80 year old great-grandmother and her 20 children. Taken circa 1965.May 28 ⋅ SuperEarth_Helldiver ⋅ r/OldSchoolCool ⋅ #1965 #20 #80
A US Navy Petty Officer 3rd Class at Andrews AFB during the inauguration of Ronald Reagan, 20 JanuaryNov 2025 ⋅ CelebManips ⋅ r/OldSchoolCool ⋅ #1981 #20
New York, 1965: Timer selfie of my mother, age 20, first night in her new apartmentNov 2020 ⋅ wishingwellington ⋅ r/OldSchoolCool ⋅ #1965 #20
My husband's great-great grandfather Big Medicine (1889 and 1910's-20's)Oct 2024 ⋅ jaded-limit ⋅ r/OldSchoolCool
60 year old photo, from 1960, of my Grandpa in his early 20's.Aug 2020 ⋅ Smellie305 ⋅ r/OldSchoolCool ⋅ #m #20 #60
My grandmother’s pilot’s license at age 20 in 1942.Mar 2020 ⋅ wilting-rose ⋅ r/OldSchoolCool ⋅ #1942 #20
Eminem and his daughter Hailie-20 years apart (Finding out he’s becoming a grandfather)Oct 2024 ⋅ Whole-Shoulder8355 ⋅ r/OldSchoolCool
My Mom (20) first time in Germany during her military years.Nov 2020 ⋅ IntrusiveThots17 ⋅ r/OldSchoolCool ⋅ #20
My grandma and her twin sister in their 20s: they were both stage artists in Poland during WWIINov 2018 ⋅ Bluewalkie ⋅ r/OldSchoolCool ⋅ #20
My Grandfather at 20 years old somewhere over the Pacific Ocean.Apr 2019 ⋅ alohamistrhand ⋅ r/OldSchoolCool ⋅ #20
20-year-old Helen Mirren dressed for her role as Cleopatra in a theatrical production, 1965May 2020 ⋅ eternalrefuge86 ⋅ r/OldSchoolCool ⋅ #1965 #20
In the photo she is about 20 years old. Photo taken around 1963-1965.Jul 2021 ⋅ DozenFrozen ⋅ r/OldSchoolCool ⋅ #1963 #1965 #20
Never had seen a picture of the Queen in her 20’s before todayJun 2020 ⋅ cwtheredsoxfan ⋅ r/OldSchoolCool ⋅ #20
In the 50s, a newspaper columnist chastised Marilyn Monroe for wearing a low-cut dress, saying she was cheap and vulgar and that she would look better in a potato sack. 20th Century Fox then shot stills of Marilyn in a form fitting burlap potato sack: the result is marvelousSep 2018 ⋅ DraftDraw ⋅ r/OldSchoolCool ⋅ #50 #20
20 year old Kane Tanaka in 1923 ..she's now the world's oldest living 'supercentenarian' and the tenthMay 2020 ⋅ eaglemaxie ⋅ r/OldSchoolCool ⋅ #f #1923 #20
My Nan and Pop, before they were married. She told me that kissing in public like this was “shocking” for the time, and she always smiles when we look at the photo. If I ever have to live in a world without her, this is how I will remember her: lively, in her early 20s, on a date with her boyfriendApr 2020 ⋅ kerplookie ⋅ r/OldSchoolCool ⋅ #20
My grandma with 20 (turned 93 yesterday)Mar 2024 ⋅ Pudelnudel ⋅ r/OldSchoolCool ⋅ #turned-93-yesterday
1957 - My Nana’s headshot, she was signed to 20th Century Fox and played a girl Zorro was rescuing on the b&w episodes for DisneyApr 2018 ⋅ TheMnemosyne ⋅ r/OldSchoolCool ⋅ #1957 #20
They lived together for over 20 years, Polly taking care of Norma when she was dying of cancer.Jul 2019 ⋅ MissMaryEli ⋅ r/OldSchoolCool ⋅ #20
, civil right activist and dentist from Japan during the Meiji Era, photo taken in 1880 when he was 20Feb 2019 ⋅ mac974 ⋅ r/OldSchoolCool ⋅ #1880 #20
We’re doing a party tomorrow with her 5 kids, 11 grandkids, and 20+ great grandkids.Jun 2018 ⋅ hellothisisJAYD ⋅ r/OldSchoolCool ⋅ #100 #20 #11 #5
My 92 year old Grandmother back in her early 20s, who always claimed she was plainJul 2019 ⋅ emsud ⋅ r/OldSchoolCool ⋅ #20 #92
Bruce Springsteen in 1970 at 20 years old, unaware that one day he'd sell 164 million records and winMay 2025 ⋅ TylerBrah99 ⋅ r/OldSchoolCool
My great-grandmother in her 20s, she turns 102 next week :-)Aug 2018 ⋅ TheLittleNome ⋅ r/OldSchoolCool ⋅ #102 #20
Then and now 1999 -2019 20 year difference, I am on the right or stage left? Jurassic park shirt!Dec 2019 ⋅ konaloop ⋅ r/OldSchoolCool ⋅ #2019 #1999 #20
Today 41 years ago, Pennie Smith photographed The Clash at the New York Palladium September 20, 1979.Sep 2020 ⋅ InsomniacNimrod ⋅ r/OldSchoolCool ⋅ #1979 #20 #41
Scarlett Johansson (13), Danielle Harris (20), and Jessica Biel (16) together at a photo shoot, 1998.Jul 2025 ⋅ TerynWhimsy ⋅ r/OldSchoolCool ⋅ #13 #16 #20
He was a fierce warrior and ultimately engaged in 20 battles, including the Custer fight in 1876.Nov 2019 ⋅ WhileFalseRepeat ⋅ r/OldSchoolCool ⋅ #1876 #1854 #1905 #1865 #20
20 years before Cobain wore clout goggles, there was Arthur Kane of the Dolls.Apr 2023 ⋅ camkai82 ⋅ r/OldSchoolCool ⋅ #20
Soviet world champion swimmer Shavarsh Karapetyan, who saved the lives of 20 people in 1976 when he sawAug 2025 ⋅ TemptedFangs ⋅ r/OldSchoolCool
My great grandmother was a burlesque dancer in New York in the 20s. She is center/bottom. I have so many pictures of her - more than any other parent or grandparent.Aug 2020 ⋅ marcyred ⋅ r/OldSchoolCool ⋅ #r/bottom. #20
Maggie Smith (Professor McGonagall) in her 20s; c. 1950s.Mar 2019 ⋅ georgiainmymind ⋅ r/OldSchoolCool ⋅ #1950 #20
Billy Idol(age 27) & Demi Moore(age 20) backstage in 1982Jan 7 ⋅ HoneyFlirts ⋅ r/OldSchoolCool ⋅ #age-20 #age-27
As a tribute to 4/20, here is an image of Snoop Dogg in his teenage years!Apr 2018 ⋅ TheMagneticDragon ⋅ r/OldSchoolCool ⋅ #20 #4
My beautiful Greek American mom age 20 1975 driving all the men crazyDec 2020 ⋅ Mosockin ⋅ r/OldSchoolCool ⋅ #1975 #20
Jack Lemmon and Walter Matthau sometime in the 90s. One of the best comedy duos of the the 20th century.Sep 2021 ⋅ TransformerTanooki ⋅ r/OldSchoolCool ⋅ #20 #90
He was murdered 20 years before I was born, but when I look at this, and see my own eyes staring backMay 2018 ⋅ curtmandu ⋅ r/OldSchoolCool ⋅ #20
They only carried 2 individual photos of them in their 20’s & had someone merge them into one inOct 2023 ⋅ Nd911 ⋅ r/OldSchoolCool
In 1985, a hardworking young man left China for the United States with only 20 US dollars, a change ofJan 2020 ⋅ SelectiveFucksGiven ⋅ r/OldSchoolCool ⋅ #1985 #20
We’ve been married for 20 years, with two kiddos and a chonk of a dog.Apr 2020 ⋅ Fluttergirl ⋅ r/OldSchoolCool ⋅ #1999 #20
It was Holocaust Remembrance Day and my mom sent these photos of my ancestors in the 20s living it up. 77 members of that side of the family would dieJan 2021 ⋅ motherofbearcats ⋅ r/OldSchoolCool ⋅ #20 #77
20 years ago I met John C Reilly during my 8th grade field trip to Chicago in the hotel lobbyMay 2021 ⋅ _bunnyholly ⋅ r/OldSchoolCool ⋅ #20 #8
My mom in her early 20s in Mexico. Her family was dirt poor so from a young age they learned how to sew and would make their own dresses.Sep 2017 ⋅ dulcelandia ⋅ r/OldSchoolCool ⋅ #20
Silent film actress Olive Thomas (1917) before being poisoned appeared in more than 20 features overMay 2021 ⋅ eaglemaxie ⋅ r/OldSchoolCool ⋅ #1917 #20
My Papa about age 19 or 20 ( 1950) long hair ,thin tache and the bullet scar on the right upper nippleSep 2020 ⋅ Jingolingo66 ⋅ r/OldSchoolCool ⋅ #1950 #19 #20 #14
Israel Kamakawiwo'ole (May 20, 1959 – June 26, 1997) He once called a recording studio at 3:00am, askedMay 2021 ⋅ jeffmartin48 ⋅ r/OldSchoolCool ⋅ #1959 #1997 #00 #15 #20 #26 #3
My dad ran the city golf course in Detroit for almost 20 years.Feb 2018 ⋅ Nightspade ⋅ r/OldSchoolCool ⋅ #97 #20
This 102 year-old man and the Rolls Royce he’s been driving since he was 20.Jul 2018 ⋅ RideShareTalkShow ⋅ r/OldSchoolCool ⋅ #102 #20
Betty Fox skipping 20 floors up, Chicago 1955Jul 2021 ⋅ GrantRichards75 ⋅ r/OldSchoolCool ⋅ #1955 #20
On September 16th, 1976, Armenian swimming champion Shavarsh Karapetyan rescued 20 people from a busOct 2017 ⋅ [deleted] ⋅ r/OldSchoolCool ⋅ #1976 #30 #20 #16
My mom at 20 years old circa 1987, in Santa Clara, CubaMar 2018 ⋅ exxcesso ⋅ r/OldSchoolCool ⋅ #1987 #20
Mom and Dad (age 20) at a Halloween Party in 1982Apr 2024 ⋅ Bananaenvious ⋅ r/OldSchoolCool ⋅ #age-20
20 YO me as an Official U.S. Army Observer at the last East Berlin May Day Parade 1988.May 2018 ⋅ Last_Century_Otaku ⋅ r/OldSchoolCool ⋅ #1988 #20
My great grandmother in her 20's (Chile, 1934)Nov 2020 ⋅ BorderLove89 ⋅ r/OldSchoolCool ⋅ #Chile #Chile,-1934 #1934 #20
Grandma and Grandpa at their wedding, January 20th, 1973. Maybe people will like this, maybe not. I think its coolMar 2019 ⋅ aleexxxisss ⋅ r/OldSchoolCool ⋅ #1973 #20
Elizabeth Taylor at 20, colorized photo (1952)Jul 2018 ⋅ ILoveRegenHealth ⋅ r/OldSchoolCool ⋅ #1952 #20
Uncle Willie during WWI, part of the 20th Engineers. Born in 1897. He died in 1928 from malaria.Sep 2021 ⋅ dessalines1804 ⋅ r/OldSchoolCool ⋅ #1897 #1928 #20
Kiefer Sutherland, 20 yrs old in 1987 while filming The Lost Boys.Jun 2025 ⋅ Ok_Dare6400 ⋅ r/OldSchoolCool
20 years old Penn Jillette working at a renaissance festival In 1975.Aug 2024 ⋅ jimlahey2100 ⋅ r/OldSchoolCool
Here's a picture of my grandfather's pilot licence, he graduated on July 20th 1918. He was the 15th person to get a pilot's licence in Mexico. Hope you enjoy it.Feb 2017 ⋅ ckarim ⋅ r/OldSchoolCool ⋅ #1918 #15 #20
My grandmother turned 100 today and is still kicking! Here is a picture of her when she was in her 20sMay 2020 ⋅ thepriceisright24 ⋅ r/OldSchoolCool ⋅ #100 #20
My grandparents on their wedding day in 1955 (ages 20 & 18).Apr 2024 ⋅ UncleBaseball88 ⋅ r/OldSchoolCool
My father after being thrown in the showers on his 20th birthday, a West Point tradition at the time. 1984Jun 2018 ⋅ YutBrosim ⋅ r/OldSchoolCool ⋅ #1984 #20
My Mom(20) and my Dad(27) in 1973 at their very first Christmas. They didn’t have much money so my dad chopped the tree down and called it their “Charlie Brown” tree. They’ve been married and been through almost 40 Christmases together.May 2018 ⋅ Whitlow14 ⋅ r/OldSchoolCool ⋅ #1973 #40 #20 #27
My Best Friend (Right side) and I meeting for the first time over 20 years ago.Mar 2024 ⋅ hallen1324 ⋅ r/OldSchoolCool ⋅ #Right-side
My parents on their wedding day on this day 20 years ago compared to todaySep 2020 ⋅ -hegel_bagel- ⋅ r/OldSchoolCool ⋅ #20
1989 Oscars: Winona Ryder(age 18) & Christian Slater(age 20)Dec 2023 ⋅ StrawberryShortcakeL ⋅ r/OldSchoolCool ⋅ #age-18 #age-20
My parents, met and married in 1987, made it through several deployments, 20 moves, two kids, and promotionsAug 2018 ⋅ Potatoviking_94 ⋅ r/OldSchoolCool ⋅ #1987 #20
My great grandfather talking a mirror self portrait. I don’t know the year, he was born in 1890 so maybe the early 20sJun 2018 ⋅ katiedee86 ⋅ r/OldSchoolCool ⋅ #1890 #20
Found this photo of my great-grandmother in her 20s as part of the Kuomintang (Chinese Nationalist Party) that fought against the Japanese invasion in China. She turned 103 this year.Jan 2018 ⋅ gummypepsi ⋅ r/OldSchoolCool ⋅ #Chinese-Nationalist-Party #103 #20
My mom one year before she became pregnant with me. At age 14. She dropped out of school in the 8th grade to take care of her siblings. She raised 4 children and went on to work for the U.S. postal service for nearly 20yrs before succumbing to cancer.Jun 2021 ⋅ mitch_8383 ⋅ r/OldSchoolCool ⋅ #20 #14 #4 #8
My parents at their wedding in 1976, they were 20/21 years oldJul 2021 ⋅ david-bowies-buldge ⋅ r/OldSchoolCool ⋅ #1976 #21 #20
A 20 year old Nancy Pelosi taking a picture with John F. Kennedy in 1961Jan 2021 ⋅ kalebsantos ⋅ r/OldSchoolCool ⋅ #1961 #20
Workers in cigar factories in the late 19th and early 20th centuries would hire lectors to read aloud newspapers, poetry and even novels to help alleviate boredom. The workers each give 25 to 50 cents of their weekly salary to elect a fellow workman to act as “the reader”.Sep 2018 ⋅ Kunalvats0 ⋅ r/OldSchoolCool ⋅ #19 #20 #25 #50
My Grandma when she was 20, 1959. She tailored all her outfits herself!Jul 2022 ⋅ ImpreciseChaos ⋅ r/OldSchoolCool
Celebrating 20 years together, and 12 years of marrige.Aug 2020 ⋅ SweetJ138 ⋅ r/OldSchoolCool ⋅ #2000 #12 #20 #8
The Twin Towers. 20 Years Later, and The World is Still Healing. Please Be Kind To A Stranger Today.Sep 2021 ⋅ Eyesalwaysopened ⋅ r/OldSchoolCool ⋅ #20
by going to Hong Kong dangerously via boat and eventually ending up staying in the UK for the past 20Dec 2017 ⋅ Lvmr ⋅ r/OldSchoolCool ⋅ #1980 #20
My gran in her late teens/early 20s. We guesstimate between 1960 - 1963. She's a natural redhead!Feb 2020 ⋅ foxlashes ⋅ r/OldSchoolCool ⋅ #1960 #1963 #20
Coast Guard for 20 years. Eventually lifting his family out of povertyDec 2016 ⋅ gogoramon ⋅ r/OldSchoolCool ⋅ #20
Brigitte Nielsen and her then husband Sylvester Stallone at the premiere of Beverly Hills cop II, 20Jan 2025 ⋅ Electrical-Aspect-13 ⋅ r/OldSchoolCool
A 20 year old Nancy Pelosi with JFK at an event in 1960Oct 2019 ⋅ benderlicious54 ⋅ r/OldSchoolCool ⋅ #1960 #20
A daredevil balances on the back legs of a chair atop other furniture, 20 stories up in New York, circaSep 2017 ⋅ Elite_lucifer ⋅ r/OldSchoolCool ⋅ #1920 #20
My mom when she was 20 years old somewhere in the countryside of Lebanon, 1987Nov 2019 ⋅ whydoilookasian ⋅ r/OldSchoolCool ⋅ #1987 #20
He would have been 59 years old today (born February 20, 1967).Feb 20 ⋅ LoudRevolution9163 ⋅ r/OldSchoolCool ⋅ #born-February-20 #born-February-20-1967 #1988 #1967 #59
She’s still just as lovely as she was in her 20’s.Jan 2018 ⋅ mellybelly92 ⋅ r/OldSchoolCool ⋅ #100 #20
February 20, 1998. 15-year-old Tara Lipinski wins the gold medal in women's figure skating at the OlympicFeb 2022 ⋅ jeffmartin48 ⋅ r/OldSchoolCool ⋅ #1998 #15 #20
Me around 1986, with my first computer, a Commodore VIC20Sep 2021 ⋅ Blend42 ⋅ r/OldSchoolCool ⋅ #1986 #20
My 20-something grandmother posing with her bedroom telephone, 1950s in Des Moines, Iowa.May 2024 ⋅ Strawb3rry_Slay3r666 ⋅ r/OldSchoolCool
My Vietnamese mother in her early 20's enjoying Cali weather, 1980s.Dec 2018 ⋅ Florence_Chloe ⋅ r/OldSchoolCool ⋅ #1980 #20
‘Cause people seem to only post the 20-something Audrey HepburnAug 2018 ⋅ [deleted] ⋅ r/OldSchoolCool ⋅ #20
Jamie Lee Curtis flew over water for 20 minutes performing the helicopter rescue scene for the film TrueFeb 2025 ⋅ eaglemaxie ⋅ r/OldSchoolCool
On August 20, 1944, young French patriots, including those in the Resistance, came out to welcome BritishMar 2025 ⋅ eaglemaxie ⋅ r/OldSchoolCool