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50 Times People Realized Their Grandparents Were Cooler Than Them

We don’t necessarily think of our grandparents as “cool”. Loving, generous, kind, and so many other things – but “cool”? Depends on how you define it, but they certainly aren’t on track with the latest trends, that’s for sure. We often forget, however, that our grandparents were young and dare I say “hip” once, too. In many cases, they may have even been cooler than us.

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50 Times People Realized Their Grandparents Were Way Cooler Than They Are

That’s right: When your grandparents were younger, they had really interesting lives. They went on adventures and did interesting things. In fact, they did things we can only imagine – and all without the help of the internet and technology. That in itself is pretty cool if you ask me.

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1. Muscle Man

Grandma Sent Me A Picture Of My Grandpa At My Age To Make Me Feel Like Shit
Image Credit: Reddit

As we age, our bodies change and get weaker. By the time we know our grandparents, they aren’t exactly the strong young bucks that they once were. This person’s grandmother decided to send them a photo of their grandpa at the same age. The grandson was quite surprised and also wondered if this was his grandmother’s subtle hint that he should hit the gym a little more often.

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2. Einstein’s Violin Teacher

My Great Grandfather Gave Einstein Violin Lessons
Image Credit: Reddit

You may think you’re cool, but are you “I gave one of history’s greatest minds violin lessons” cool? This person’s great grandfather is cooler than all of us. There is no doubt.

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3. Always Down For A Fun Joke

My Grandparents Wearing Each Other's Clothes, 1943
Image Credit: Reddit

This person’s grandparents clearly knew how to have fun. This photo is of their grandparents after swapping each other’s outfits. The headscarf looks good on grandpa, I think!

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4. The Beauty Queen

My Grandmother, 1940s
Image Credit: Reddit

Miss America? A famous actress? A musical star? Nope – just this person’s grandmother in the 1940s.

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5. The Dare Devil

Granny On The Wing Of My Dad's Cropduster Plane. She Did This A Few Times That I Know Of
Image Credit: Imgur

First off, this person’s grandfather had and regularly flew a plane. Second off, and the most impressive part, was how his grandmother liked to ride in – or rather, on – it. We hope some of her adventurous spirits rubbed off on her grandkids.

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6. Living By Her Own Rules

My Grandmother. This Picture Was Next To Her Coffin At Her Funeral (Late 60s Or Early 70s)
Image Credit: Reddit

This was the photo placed beside this person’s grandmother’s coffin at her funeral. Not only did this woman clearly have a sense of humour, but she also had a rebellious streak in her, too.

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7. Teaching The Men

My Granny (Nicknamed Kidd) Wasn't Allowed To Join The Air Force Because She Was A Woman. So She Taught Young Men To Fly In Stephenville, Texas During WW2 - 1940s
Image Credit: Reddit

Back in the 1940s, this person’s grandma wasn’t allowed to join the airforce because she was a woman. Nicknamed Kidd, instead, she turned to teaching… the men how to fly their planes. She taught fighter pilots how to fly throughout WWII and the 1940s.

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8. Timeless Good Looks

My Grandfather The Day Before He Shipped Out With The Marines, 1941
Image Credit: Reddit

People from every generation can agree that this man is rather good-looking. You could put him in any era and he would be a heartthrob. There’s one thing for sure: This person’s grandma was a lucky woman!

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9. The Runaway

My Grandmother Right After She Ran Away From Communistic Bulgaria To Germany (1978)
Image Credit: Reddit

This photo was taken right after this person’s grandmother fled communist Bulgaria for Germany. I don’t know about you, but I don’t think I’d be looking quite so good after that journey.

10. The Definition Bravery

Photo Of My Grandfather Exiting His Plane After Getting Shot Down
Image Credit: Reddit

Is it just me, or were people back in the day just tougher? This is a photo of this person’s grandfather exiting his plane after it was shot down in WWII.

11. The Image Of Strength

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 3 Am - 5 Pm. I Would Stay Every Weekend With Her And Sleep On The Floor Of The Gas Station Back Then. She's Amazing
Image Credit: Reddit

When our grandmothers were our age, there weren’t very many options for women. This picture of this person’s grandmother is from 1942. It was taken while she was in the midst of single-handedly raising six children after leaving an alcoholic husband. She worked every single day from 3 am to 5 pm as a cook in a gas station to support her family.

12. Stay A Little Crazy

My Crazy Grandfather
Image Credit: Imgur

This person’s grandfather worked for the LA Times as a photographer for over 50 years. He took many famous photos, including the first photo of the atomic bomb. He was funny, a tad crazy, and always making others smile. He lost his wife and two sons and battled prostate cancer for over 20 years. Despite the struggles, he never lost his sense of humor.

13. Cosplay Or Just A Jokester

My Grandfather Was Into Cosplay Before It Was "The Thing To Do"
Image Credit: Imgur

We’re not sure why this guy’s grandpa is dressed up like a chicken, but one thing is for sure – he doesn’t care what we think. I think the definition of cool is being 100% authentically yourself and not worrying about other’s opinions. That makes this man the coolest around.

14. Old School Cool

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
Image Credit: Reddit

Okay, I don’t condone smoking but just look at this guy! Holding the fish he just caught, cigarette in his mouth, book tucked into his pants, and cigarette pack in his sleeve. Clearly, a catch like that wasn’t very tough for this man. Effortless and casual.

15. Rebel Woman

My Grandma Smoking Her Cigarette On The Farm. Wearing Pants And Doing Whatever The Hell She Wanted, 1938
Image Credit: Reddit

This is a photo of this person’s grandma from 1938. It may look casual, but it’s far from it. It’s the 1930s, and yet she is wearing pants and smoking a cigarette with a look that just says “Don’t tell me how a woman should act or dress”. Talking about taking a stance against gender stereotypes.

16. Guts And Glory

WW2 - My Badass Grandpa With A Car He Stole From Nazis
Image Credit: Reddit

This is a photo of this person’s grandfather posing with the car he stole from the Nazis during WWII. I don’t think very many of us have the guts that this guy did.

17. Old Hollywood Glam

I Recently Lost My Grandmother To Cancer. This Will Always Be One Of My Favorite Photo Of Her
Image Credit: Imgur

It’s hard to picture our grandparents as once young, dare I say, sexy people. This photo of this person’s grandmother reminds us that not only were they gorgeous, but they were also classic.

18. Who’s The Star-Struck Ones?

My Grandmother With Then-Mercury 7 Astronauts John Glenn, Gus Grissom, And Alan Shepherd (September 14th, 1959)
Image Credit: Reddit

This is a photo of this person’s grandma with the Mercury 7 astronauts John Glenn, Gus Grissom, and Alan Shepherd. I’m not sure who’s happier to be taking the picture with who, however.

19. The Great Rider

My Great Grandfather Showing Off One Of The Horses He Trained For WW1 - Petawawa, ~1922
Image Credit: Reddit

You might be cool, but are you riding-a-horse-through-an-obstacle-course-that’s-on-fire cool? Likely not. This photo is of this person’s grandfather showing off one of the horses he trained for WWI.

20. The Samurai

My Great-Great Grandfather, The Samurai Of A Small Coal Mining Town In Kyushu, Posing With My Grandmother And One Of Her Sisters ~1900
Image Credit: Reddit

This person’s great-great-grandfather was an actual Samurai. His job was to protect the small mining town in Kyushu, Japan. What’s cooler than that?

21. A Woman In A Man’s World

My Great Grandmother, Working As A Welder During WW2
Image Credit: Reddit

The men may have been the ones on the front lines of the great wars, but it was the women at home who stepped up and kept the country going. This is a photo of one person’s grandmother who worked as a welder during WWII.

22. Water Skiing Champion

My Grandfather Died Today. I Want To Tell You What A Fucking Badass He Was
Image Credit: Imgur

Do you consider yourself a good water skier? How about good enough to do so while carrying someone on your shoulders? This guy’s grandfather is that cool. He’s looking at the camera so casually, too.

23. True Love

My Grandma Recently Passed. My Grandpa Sent Me This Picture So I Could Know What Man Looks Like When He Is In Love. They Were Married 60+ Years
Image Credit: Imgur

After their grandmother died, this person’s grandfather sent them this photo of the couple. He wanted them to know what it looks like when a man is truly in love.

24. The Original Tiger King?

If I Could Only Be Half As Badass As My Grandfather This Memorial Day, Circa 1960
Image Credit: Reddit

Okay all jokes aside, I’m not sure where he got the tiger cub or why he has it but it’s still pretty cool. We have to keep in mind here that we don’t know the context of this photo before we jump to conclusions about cruelty.

25. Style Icon

My Great Grandpa Eddie. Omaha 1939
Image Credit: Reddit

It can’t be argued that this man’s got swagger. No doubt he tipped his hat and leant a dashing grin to everyone he met. Whatever he’s selling, we will buy it all.

26. The Aviator

My Grandma As An Air Traffic Controller. She Would Have Been 97 On 3/11
Image Credit: Reddit

Well, sort of! Being an air traffic controller is a high-stress job. This woman’s grandmother, however, is too cool to be stressed. She’s looking rather laid back in this photo.

27. Easy Summer Living

My Grandfather's Badass Swandive, 1930
Image Credit: Reddit

This person’s grandfather had the swan dive down to an art. Just look at this picture – absolute perfection.

28. The Fox And The Man

My Finnish Grandfather Smoking A Cigarette And Holding A Wild Fox That He Befriended (Circa 1975)
Image Credit: Reddit

Someone tell Pixar about this photo. This person’s grandfather befriended a wild fox in the 70s. This is the photo evidence.

29. Pure Happiness

This Photo Always Puts A Smile On My Face. Our 86-Year-Old Grandmother Back In The Day
Image Credit: Imgur

We’re not sure if she was a flight attendant or was simply travelling, but wow does she look like she enjoys life. No wonder it’s this person’s favourite photo of their grandmother.

30. The Filght Attendant

My Grandma Modeling In Her Flight Attendant Uniform - 1972
Image Credit: Reddit

This person’s grandmother was a flight attendant in the 70s. This is a photo of her modelling the uniform.

31. The Trailblazer

My Great-Grandmother In Her New Car. She Was Most Likely The First Indian Woman In The Western US To Own A Car (April 7, 1916)
Image Credit: Reddit

This person’s grandmother was one of the first Indian women in the western United States to own a car. She likely had to fight against a lot of prejudice because of this. After all, it was only 1916.

32. The War Hero

Grandmother Died Last Week, She Was A Naval Nurse
Image Credit: Reddit

When we talk about war heroes, we often talk about the people who fought in the war. What about, however, the brave women who worked as nurses, doing their best to save the lives of the injured men in their care? This grandmother was a navel nurse and no doubt saved many people’s lives.

33. The Date

My Grandparents In 1960, On A Date. My Favorite Picture
Image Credit: Reddit

This is a photo of this person’s grandfather on a date in 1960. We don’t know what the outcome of this date was but it certainly looks like they were having a good time.

34. Man And Bear

So Apparently My Grandpa Was A Badass
Image Credit: Reddit

This person’s grandfather clearly fears nothing. Here he is, looking like he’s having casual cooler talk with a black bear.

35. Biker Chick

My Grandmother On Her Harley In 1926
Image Credit: Pinterest

Are you bad*ss enough to ride a Harley in a dress? This person’s grandmother was. This picture is of her and her very own Harley Davidson motorbike in 1926.

36. The Spy Recruiter

My Grandpa's FBI Academy Photo. He Worked As A Spy Recruiter During The Cold War
Image Credit: Reddit

I mean, he even looks the part! This grandfather worked as a spy recruiter during the Cold War. This is his spy academy photo. Again, this feels like a movie waiting to happen.

37. The Volvo Model

My Grandmother Demonstrating The Three-Point Belt As A Model For Volvo In 1959
Image Credit: Reddit

The year is 1959. Volvo just came out with its three-point seatbelt. This person’s grandmother was chosen to model this new safety feature for the car company.

38. Do Not Disturb

The Last Photo In My Grandparents Wedding Album (1954)
Image Credit: Reddit

This is the final photo in this person’s grandparents’ wedding photo album. After all, it’s their special night – and they don’t care who knows what!

39. The Bomb Difuser

My Grandfather Defusing A Bomb On Martin Luther King's Porch. He Was Buried Three Years Ago On MLK Day
Image Credit: Imgur

This photo is of this person’s grandfather defusing a bomb on Martin Luther King’s front porch. Not very many people can say they were responsible for the security of one of the nation’s most prominent figures. That is pretty cool.

40. The War Nurse

My Grandmother Turned 98 This Week. This Is Her In Her Full Nursing Uniform During WW2
Image Credit: Reddit

Likely this person has memories of their grandmother nursing their scrapes when they fell down or taking care of them when they were sick. Well, turns out, their childhood challenges were a cakewalk in comparison to her former job. She was a nurse during WWII.

41. A Many Of Many Lives

My Stud Grandfather Circa WW2. 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
Image Credit: Reddit

“My Stud Grandfather Circa WW2. 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

42. Casual Conversation

Ernest Hemingway And My Grandma Having A Chat In Havana, Cuba 1952
Image Credit: Reddit

This is a photo of this person’s grandmother having a casual chat with Ernest Hemmingway in Havana in 1952. While opinions on the man may be mixed, it’s still pretty cool to see her chatting with such a well-known person.

43. Summer Lovin’

My Friend's Grandparents, California, 1940s
Image Credit: Reddit

Cool car, beautiful couple, and the California sunshine. This person’s grandparents knew how to roll back in the 1940s.

44. Arya Stark, Is That You?

My Grandmother Looked Like Arya Stark In 1936
Image Credit: Reddit

Okay, no, this isn’t Arya Stark from Dr. Who. It’s this person’s grandmother in 1936. The resemblance is uncanny, however.

45. Ride To Freedom

My Grandfather On A Motorcycle He Stole From A Nazi, Weeks After American Troops Liberated Him From A Concentration Camp In Landsberg, Germany (May 1945). He Had Spent 4 Years In Concentration Camps Around Poland And Germany
Image Credit: Reddit

“My Grandfather On A Motorcycle He Stole From A Nazi, Weeks After American Troops Liberated Him From A Concentration Camp In Landsberg, Germany (May 1945). He Had Spent 4 Years In Concentration Camps Around Poland And Germany

46. Her Favourite Lion

My Grandmother With Sultan, Her Favorite Lion From Her Troop, In Front Of Her Plane She Flew Just After WW2 (1947)
Image Credit: Reddit

Do you have a favourite lion? This person’s grandmother did, and his name was Sultan. This is the two of them together in front of the plane she flew in 1947.

47. The Best Beard In Town

My Grandfather After Winning 1st Place In The County Beard Contest. The Hat Was His Prize. Circa 1954
Image Credit: Reddit

Plenty of people can grow a beard, but can you grow the best beard? This person’s grandfather is pictured here after winning first place in the county beard contest. The prize? Why, the grand old hat on his head.

48. The Dancer

I Would Always Call My Grandmother On Mother's Day, And Have Missed That Call For A Few Years Now. Thought I Would Share This In Her Honor
Image Credit: Reddit

Our grandparents lived entire lives before we were even born. This person’s grandmother was a ballet dancer.

49. World War Two Worker

My Grandma (Top) Was A Badass In Ww2 (1940s)
Image Credit: Reddit

This person’s grandmother (the top woman in this photo) did important work during WWII. Women truly go underappreciated when talking about the war.

50. The Protector

Don't Mess With My Great Grandmother Emma Hagen, Woman Homesteader In North Dakota, 1910s
Image Credit: Reddit

The world was a different place in 1910. This is a photo of this person’s great-grandmother protecting her home in North Dakota. This woman clearly had no fear, or at least refused to show it.

We often forget about the incredible lives our grandparents lived before we were born. If you are lucky enough to still have yours, go ask them about it. At the very least, see if you can get your hands on some old photo albums and learn a little bit more about their lives – and your family history.

Keep Reading: Why a Maternal Grandmother Is So Important for a Child

Julie Hambleton
Freelance Writer
Julie Hambleton has a BSc in Food and Nutrition from the Western University, Canada, is a former certified personal trainer and a competitive runner. Julie loves food, culture, and health, and enjoys sharing her knowledge to help others make positive changes and live healthier lives.
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