Grandparents who were cooler than we ever could be
Sometimes, it’s easy to forget that our grandparents used to be young, hip people with dreams and aspirations of their own.
These people posted photos online of their grandparents back in the day. Apparently, people in the ’40s and ’50s were way cooler than we are.
Is That A Tiger In Your Bag?
A Reddit user posted this image online with the caption, “If I could only be half as badass as my grandfather this Memorial Day, c. 1960.”
We’d settle for being a quarter as cool.
Effortlessly Cool
A Redditor posted this image of their grandmother, showing her as she was on a vacation in 1976 at the age of 23.
The post also included earlier and later photos, summarizing them by saying that she’s aging like a fine wine.
Putting On A Show
The man in this photo died recently, but his granddaughter posted this photo online to show everyone how cool he was back in the day.
Are you a waterskiing champ? Didn’t think so.
This Is Sweet To See No Matter What Era You’re In
Although it’s unclear what year this taken in, we do know that Reddit user ghostinghumanity’s grandmother was born in 1930, so this was likely some time in the late ’40s or early ’50s. In either case, her endearing smile while having a wholesome bike ride with her little dog is still heartwarming decades later.
Unfortunately, the reason that the uploader happened to come across this picture was that she had passed away recently and they needed photos for her visitation. This would be a lovely one to include.
The Coolest Way To Tell Fascism Its Days Are Numbered
Although he happened to be riding his bike in front of it that day, Reddit user fightography’s great uncle would soon be flying a combat mission in an appropriately named plane during World War II.
While it’s hard to think of a combat role that wasn’t risky at the time, those in the Air Force had some grim odds for making it back alive after an attack run. The fact that the plane has either “Mk. II” or “Mk. III” next to its name (the image quality makes it hard to tell), is enough of an example of that.
This Bar Didn’t Take Long To Stop Existing
This dapper couple were spending their honeymoon in Havana, Cuba, where they stopped for a drink in a bar called Sloppy Joe’s. Since their honeymoon was in 1939, it would be about 20 years before the nation became a very unfriendly place for Americans.
Although Sloppy Joe’s was able to hang in there for a few years after the Cuban Revolution, it closed its doors in 1965. However, it managed to reopen in 2013.
Meeting A Literary Genius
Reddit user mattmanatee posted this photo online with the caption, “Ernest Hemingway and my grandma having a chat in Havana, Cuba 1952.”
Yup, his grandma was friends with Ernest Hemmingway.
Turning Heads
This photo shows quintessential 1940s fashions, from the stylish dress worn by the woman in the foreground to the dapper hats on the men in the background.
It was posted by the woman’s great granddaughter. One commenter pointed out that she’d clearly caught the attention of a man on the right side of the photo, just over her left shoulder.
Up, Up And Away
Reddit user di11deux posted this photo online with the caption, “My grandmother with then-Mercury 7 astronauts John Glenn, Gus Grissom, and Alan Shepherd (September 14th, 1959).”
What an out-of-this-world encounter!
Don’t Smoke, Kids
With the caveat that smoking is not an advisable habit, this photo — showing a Redditor’s Austrian grandmother in the early 1970s — is downright gorgeous.
From the lush colors of the grass to the various textures — hair, shirt, grass — the composition in this photo is incredible.
This Man And His Car Saw Some Real Adventures Together
As Reddit user maricopa65 explained, this photo was taken in 1964 and depicted their grandfather posing with his prized Chevrolet Corvair. Although its retro style speaks for itself, the car also proved reliable to him.
That’s because he took it across the whole country from Washington state to New York twice in both his lifetime.
They Remained Friends For Life
Reddit user kriegzter identified the man on the right as their grandfather, Bennie. He was serving in the Air Force during the ’60s alongside his friend Jim, whom he’d drink with at the VFW long after both of their retirements.
Unfortunately, kriegzter was devastated to learn that after some promising updates at the hospital that included an imminent discharge date, Bennie suddenly passed away.
It Didn’t Get Cooler Than This In The ’30s
Although the 1930s couldn’t be described as a particularly good time for practically anyone in the world, people throughout the globe found their ways to make the most of it.
For instance, while it’s unclear where Reddit user itsBigSmokeBruh’s grandfather was going on this motorcycle while living in the Netherlands, it was clear he was riding in style.
A Face Like A Movie Star
This photo of Reddit user FinneganWelles’ grandmother was taken in the 1940s. She looks like a movie star in this picture.
She wasn’t actually an actress, but this photo could have fooled us.
An Early Bikini
By the 1950s, when this photo was taken, bikinis weren’t quite a brand-new invention — but that said, they hadn’t been around for long, either.
Named for Bikini Atoll during World War II, this style of swimwear was considered risqué at best and downright scandalous at worst by many.
A WWII Hero
Reddit user alexanderbatman posted this photo online with the caption, “My grandma (top) was a badass in WW2 (1940s).”
This shot looks like something out of a Charlie Chaplin movie.
Deadliest Catch
This photo almost looks like it could have been taken yesterday, but it’s actually more than 70 years old. The poster explained that it shows their grandma at the age of 19 in 1950 or so, jokingly clarifying, “my grandma is the one on the right.”
While she’s dressed down in casual workwear, one commenter noted her facial resemblance to the model Kate Moss.
A Prize-Winning Beard
Reddit user jobernaut posted this picture online with the caption, “My grandfather after winning 1st place in the county beard contest.
The hat was his prize. Circa 1954.” That is a stellar beard. He definitely deserved the hat.
Is That A Young Susan Sarandon?
This isn’t a picture of Susan Sarandon from the past. It’s just her doppelganger standing between a plane and a lion.
Reddit user Rizodominus posted this photo with the caption, “My grandmother (again) with Sultan, her favorite lion from her troop, in front of her plane she flew just after WW2. 1947.”
Ready to Impress
Long before the age of modern bodybuilders, this Redditor’s grandpa is displaying an impressive physique while posing by a swimming hole.
The photo was taken in 1947, and the rich colors, sunshine, and friendly smile all point to a spirit of post-war optimism.
A Girl Has No Name
Reddit user Gamble_MK9 posted this picture online because he felt like his grandmother bore a striking resemblance to Arya Stark when she was younger.
This photo was taken in 1936.
It Means A Lot To See What Your Grandparents Believed In
According to Reddit user tossedtides, this is a picture of their grandfather during the early ’70s. As the poster behind his friendly face makes clear, he was an ardent supporter of the Chicano Movement, which was inspired in many ways by the activism of Cesar Chavez.
But while his movement was more specific to farm labor, the movement had more high-level goals of fighting against structural discrimination and placing enough value in one’s culture to resist assimilation.
They Weren’t Fighting But They Were Still At Risk
As Reddit user Mommyof2Muggles explained, the man at top center in this photo is her great uncle Leslie, who was a merchant marine during World War II along with his crew.
This meant that they were engaged in wartime shipping rather than naval battles, but that didn’t mean they were any safer than a Navy vessel. German U-boats didn’t like seeing their enemies supplied, after all.
This Would Be A Rare Opportunity
According to Reddit user xabi, this picture depicts both their father (at left) and his friend while on the set of the 1960 film Spartacus. While not many people can say that, it’s easy to forget how many people besides the stars acted in that movie.
When you’re depicting epic battles against Roman legions, for instance, you’re certainly going to need a lot of extras. Naturally, those extras will start families just like anybody else.
So Many People Would Want That Cat Purse Now
Although most people upload images of their parents or grandparents while looking back to the past, Reddit user dittidot is apparently old enough to have been a little girl in 1957.
At the time, she was visiting her grandma’s house with her adorable dog in tow and clutching this stylish cat purse. Everything about this picture is so cute.
Dressing Casually
Older photos often show people who are dressed to the nines, so it’s somewhat refreshing to see a vintage photo that shows someone in comfortable, casual wear.
This 1961 photo shows a young man who’s 20 years old and would go on to have a family — including a grandchild who would one day post this photo
A Real Stud
Reddit user i_hate_pennies posted this photo online with the caption, “My stud grandfather circa WWII. He watched Pearl Harbor happen in Hawaii, joined up, and fought on a gunboat at Iwo Jima that was hit by enemy fire.
He surfed with legends in Honolulu. He was a barber for 60 years.”
A Rockin’ Wedding Night
This is the last photo in Reddit user bluestofwaffles’ grandparents’ wedding album. They seem like they have a good sense of humor.
Hopefully, their wedding night was full of laughs and lots of love. This photo was taken in 1954.
Navy Days
In an era before tattoos were ubiquitous, seeing a man with tats like this meant that he had likely served in the armed services, specifically the Navy.
Indeed, that’s exactly the case here, as this 1955 photo shows a fresh-faced 18-year-old shortly after enlisting in the Navy.
A Real Seat Belt Model
Reddit user Mashedbymachines posted this photo of his grandmother online with the caption, “My grandmother demonstrating the three-point belt as a model for Volvo in 1959.”
His grandmother was a literal model.
Surveying His Domain
This 1967 photo should feel familiar to anyone who grew up during the decade, as the shirtsleeves, pipe, and hairstyle are all emblematic of 1960s dads.
At the time the photo was taken, the subject was 33 years old, prompting many Redditors to note that “33 just hit different back in the day.”
Looking Like A Film Noir Detective
Reddit user sw00n might just have the coolest grandpa on this list.
He posted this photo online with the caption, “My grandpa’s FBI Academy photo. He worked as a spy recruiter during the Cold War.”
Ahead of His Time
The late ’50s were a buttoned-down time, an era in which most men wore suits, fedoras, and kept their hair neat and trimmed.
The man in this photo is hardly a beatnik, and the hippie years are still in the future, but there’s something about his casual style, sideburns, and hairstyle that carries a hint of countercultural rebellion.
Yes, That’s A Bear
Reddit user AdventurousHuman’s grandfather ran into a bear while he was out riding his motorcycle back in the day.
He doesn’t seem too phased about the fact that there’s a large, dangerous animal behind him.
The Look Of Love
Reddit user atothego posted this adorable photo.
They captured it: “My grandma recently passed. My Grandpa sent me this picture so I could know what a man looks like when he is in love. They were married 60+ yrs.”
A Welder Chick
This is a photo of Reddit user anonymous-horror’s stunning great-grandmother.
This woman worked as a welder during the Second World War. She looks like she’s way too cool for school.
A Fancy Dress
Reddit user jewelsinme posted this photo of her grandmother online with the caption, “My favorite picture of my grandmother. 1942. She’s strong, raised six children on her own after leaving an alcoholic husband.
Worked 7 days a week as a cook in a gas station from 3am-5pm. I would stay every weekend with her and sleep on the floor of the gas station back then. She’s amazing.”
An Actual Pin-Up Model
Reddit user wefoundeachotherinthedark posted this photo of her grandmother online.
She added the caption, “I recently lost my grandmother to cancer. This will always be one of my favorite photos of her.”
A Stolen Car
It doesn’t get much cooler than Reddit user ksm2721’s grandfather.
The grandfather in question is pictured above, along with a car that he stole from the Nazis during World War II.
A True Hero
Reddit user gettingthere52 posted this absolutely epic photo of his grandfather online.
He added the caption, “Photo of my grandfather exiting his plane after getting shot down.” His plane is in the ocean, people!
Lounging Around
Reddit user bringdoughnuts posted this photo online along with the caption, “My grandma smoking her cigarette on the farm. Wearing pants and doing whatever the hell she wanted. 1938.”
What a smoke show!
The Original Chicken Man
This guy was the original cosplayer. Apparently, people dressed up as chickens back in the 1930s.
All you hipsters probably wouldn’t be caught dead in a true vintage outfit like this one.
Yes, That Is Albert Einstein
Reddit user TheTimeIsChow posted this photo of his grandfather standing next to Albert Einstein on the internet for our viewing pleasure.
It looks like Einstein had just finished playing the violin.
Absolutely Stunning
Reddit user wlyff posted this photo of his grandmother online with the caption, “My grandmother right after she ran away from communistic Bulgaria to Germany (1978).”
Germany gained an absolutely stunning citizen that day.
The Old Switcheroo
Reddit user howdidyougetin posted this photo of his grandparents wearing each other’s clothes back in the day.
This photo was taken in 1943. His grandfather looks stunning in that dress.
Granny On A Cropduster
Imgur user silvervendetta shared this incredible photo and had this to say about it.
“Granny on the wing of my Dad’s cropduster plane. She did this a few times that I know of.” Wow, that’s a daredevil grandmother!
The Day Before Shipping Out
Wow, what a hunky grandpa! Redditor aking25 posted this pic of their model-esque grandfather.
They wrote that this was the day before he shipped out with the Marines in 1941.
Loving Nurse
Redditor orion12 sure loved their grandma and were kind enough to share this stunning picture of her in her days as a Naval nurse! What a stunner.
They wrote, “Grandmother died last week, she was a naval nurse.” The photo is from WWII.
So Your Grandparents Had Horses Too?
Did they look anything like this? We doubted it. Redditor FutureMillionaire_ says this photo is of their grandfather, who is “showing off one of the horses he trained for World War 1.”
The picture was taken in 1921. That’s incredible.
Epic Swandive
Posted by Reddit user not_blinking, this photo shows a now-grandfather taking an epic swan-dive off a building and into a lake, circa 1930.
What is he, part merman or something?
Motorcycle For Sale
Well, this photo certainly tells a whole story. It seems like that motorcycle might be the reason why this guy has a broken leg.
This photo was taken back in 1976.
Meeting The One And Only B.I.G.
Reddit user sloanmar posted this iconic photo online.
He captioned it: “My dad and the Notorious B.I.G. circa 1996 when he visited my dad’s clothing store in Detroit, Michigan.”
Just A Group Of Friends Having Fun In The ’80s
Could this picture be any more ’80s? Reddit user tomjulio posted this photo of his parents and their group of friends online.
The short shorts were really, well, short in the ’80s.
She Jumped On Stage
Reddit user se7en30 posted this photo online.
They captioned it: “My aunt with Angus Young in the early ’80s. This was taken after she went out on stage with AC/DC and just kind of jumped around wearing the iconic schoolboy outfit.”
A Wedding To Remember
This Reddit user spent some time restoring her parents’ wedding photo. Now it looks as good as new.
This photo was taken in 1957, which was a heck of a long time ago.
Sneaking A Drink
This photo was taken in 1987. This kid (who is now a parent himself) was sneaking a drink of wine at a wedding when his mom wasn’t looking.
Kudos to the photographer for capturing this shot.
Mom In The Early ’70s
Reddit user puggernault shared this picture of his mom from the early ’70s.
We’re not sure how she managed to ride that motorbike in a long skirt, but hey, she looks great standing next to it.
Just A Couple Of Kids
Reddit user jensinec posted this photo of her parents online along with the caption, “My parents in the early ’80s during their honeymoon with matching sneakers.”
Well, aren’t these two the very definition of “cool.”
The Coolest Man Who Ever Lived
Everything about this photo reeks of coolness. The gray streak in this guy’s hair, the way he’s sitting on the grass, his Johnny Depp swagger. I love this.
Apparently, this guy was always self-conscious about his hair because he was teased about it as a kid.
What A Hairdo
Reddit user Maire13 posted this photo online. This is a picture of her mom that was taken by her dad in 1966 in Japan.
We love the big hair and the winged eyeliner.
Dangerous Curves
Well, it looks like somebody’s grandmother had a sense of humor.
Reddit user YiddishThunder posted this photo online along with the caption, “My Grandmother Nancy on her honeymoon near Capitan, NM. Taken by my grandfather on a Kodak Kodachrome, 1949.”
Hanging Out In A Van
Reddit user kwgnuemu posted this photo online stating that this picture of his parents was taken in 1974.
They’re standing in front of the van that was most likely the site of his conception.
A Popeye Impersonator
Reddit user Idkm8thisishard posted this photo of his great grandfather on the internet. Yes, his great grandfather was a Popeye impersonator.
This photo was taken in the 1930s. He looks like quite a character.
At The Helm Of The Ship
Reddit user jeffpeepgrass posted this photo online along with the caption, “My Uncle Billy just turned 90, so here’s him on his boat during the early ’80s.”
He’s the captain now.
On The Set Of A Movie
Reddit user GoodSquirrelGoneBad shared this photo of his dad working on the set of the movie Critters in the 1980s.
It looks like some of the critters in that film were rather terrifying.
Mom And Dad
This photo was taken in 1987 when Reddit user hlg97’s parents were 16 and 17 years old. These two are still together to this day.
They look so punk rock in this photo.
His Mom Dated Jason Bateman
Reddit user bhuge33 posted this photo online.
They captioned it: “Talking with my mom about Ozark and she told me she went skiing with Marty Byrde (Jason Bateman) back on New Year’s Day 1987.”
Hitting The Pavement
Reddit user fulltimeanalyst posted this photo online.
It features his father carving up some pavement on his skateboard back in the 1980s. He looks like a pretty cool dude to me.
Is That Chris Pratt?
Reddit user deeznuts3295 posted this photo of his father online. Is it just me, or does his dad look an awful lot like Chris Pratt?
Does this mean that Chris Pratt is a time traveler?
Every Guy’s Tinder Pic
Reddit user schants posted this photo online with the caption, “My very cool grandpa in the 1950s holding a fish, smoking a cigarette, with a book tucked into his pants and cigarette pack in his sleeve.”
You know how every guy seems to have a picture of himself with a fish on his Tinder profile? This is what they’re all trying to achieve.
A Fox For A Friend
Reddit user TheKingStacker posted this photo of his very cool grandfather online.
He captioned it, “My Finnish grandfather smoking a cigarette and holding a wild fox that he befriended. (Circa 1975).”
