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95 Times People Captured Some Of The Coolest Moments In History That Now Transcend Generations

95 Times People Captured Some Of The Coolest Moments In History That Now Transcend Generations

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Scrolling online these days often feels predictable. Social media is filled with either vitriolic, divisive content or the same manufactured images from creators who strive for perfection. 
But sometimes we come across awesome content that compels us to share it or stop what we’re doing and dig deeper. You may find that kind of content in this subreddit, with a name that perfectly captures what it is all about. 
Here are some posts from the group that may spark your curiosity today. Enjoy scrolling, and upvote the ones that hook you and make you want to know more.

#1

Bessie Stringfield posing on her motorcycle, representing one of the coolest moments in history.
Meet Bessie Stringfield, the Black woman who rode a Harley solo across Jim Crow America eight times in the 1930s and 40s. She slept on her bike when hotels turned her away, won a flat track race disguised as a man, carried Army dispatches in WWII and became the Motorcycle Queen of Miami.
35points

#2

Black and white vintage photo capture of Bette Davis conversing with a female military officer, one of coolest moments in history.
Bette Davis was the only white performer who agreed to be part of Hattie McDaniel’s performing troupe to entertain Black servicemen during WWII.
34points

#3

Historical photo of a one-eyed kitten named One Eye Pete, capturing cool moments in history.
Tough One-Eye Pete circa 1890.

Sending love to Pete, psps psps from 2026.
33points

Most of us use the word “cool” to describe something we deem amazing, yet many may not know where it came from. For the uninformed, the word’s modern usage traces back to the Second World War, thanks to African American Jazz musicians in the 1940s. 

As author and educator Joel Dinerstein explains: “An icon of cool is a person who has created or inspired social change through art, protest, or popular culture.”

#4

Vintage photo strip of a man posing affectionately with his dog, one of the coolest moments in history.
In 1943 a man and his German Shepherd took some time out to pop into a photobooth in Grand Central, NYC. I'm glad they did.
32points

#5

A man wearing a hat drives an ornate metal mesh custom car outdoors, capturing cool moments in history.
The Volkswagen “Wedding Beetle,” a fully functional car with a floral wrought iron bodycreated by mexican blacksmith rafael esparza-prieto in 1968, it was originally built to attract customers to an auto parts business.
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32points

#6

Historic photo of pioneer aviator Bessie Coleman posing next to her biplane in one of the coolest moments in history.
Meet Aviator Bessie Coleman, the first African-American woman and first Native-American woman hold a pilot's licence. Also the earliest known black person to obtain an international pilot's license from the Fédération Aéronautique Internationale in 1921.
31points

According to Dinerstein, the word itself first came from Lester Young, a star saxophonist from the Count Basie Orchestra. At the time, he used it to describe feeling safe, relaxed, and laid-back. 

It also had a political context, as it was used as a protest for the racial segregation during the Jim Crow Era.

#7

Young boy standing behind a detailed cardboard stadium model, capturing one of the coolest moments in history.
Jorkiam Samba Mampuya, a young boy from Kinshasa, Democratic Republic Congo, built a football stadium model entirely from old cardboard. He would someday like to become an architect.
Artistic expression has no boundaries.
29points

#8

Sigourney Weaver testing a flamethrower prop on set, representing iconic film moments in history.
Sigourney Weaver trying out a flamethrower for Alien on the lawns at Shepperton Studios in 1978.
27points

#9

Historical Wooden sculpture of Mephistopheles reflecting as Margarethe in a mirror, a cool moment in history.
This is popularly known as the “Double Statue of Mephistopheles & Margaretta”, the sculpture is carved out of a single log of sycamore wood and has two distinct images on either side. It was acquired by Mir Turab Ali Khan (Salar Jung I), in 1876 during his travels in France.
27points

“‘I’m cool’ meant 'I’m keeping it together—in mind and spirit—against oppressive social forces,’” Dinerstein wrote, explaining how people used the word in this context. 

Dinerstein further noted that the word cool had been around a little while longer in the 1930s. At the time, people used it to calm someone down from emotional stress.

#10

Aerial view of the Dalhalla amphitheater in a quarry, one of the coolest moments in history.
Carved from an abandoned limestone quarry in central Sweden, Dalhalla is a breathtaking open-air theatre. Located just north of Lake Siljan and the municipality of Rättvik in Dalarna,.
27points

#11

Ella Fitzgerald singing passionately on stage, representing one of the coolest moments in history.
Ella Fitzgerald at Mister Kelly’s nightclub, Chicago, 1958.
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25points

#12

Vintage black and white photo of a child backstage watching a dancer perform, capturing coolest moments in history.
On this day in 1957, Carrie Fisher was born in Burbank, California, USA. She was best known for playing Princess Leia in the Star Wars film series. Here she is watching her mother Debbie Reynolds perform on stage. (1963).
25points

Everyone wants to be branded as “cool” in their own right. So much so that academics have their own “Theory of coolness” and the four traits that may define a person as such. 

According to behavioral scientist and marketing professor Dr. Lalin Anik, these four As are Autonomy, Authenticity, Attitude, and Association.

#13

Detailed view of an ornate vintage shell-shaped vanity kit, capturing historic craftsmanship.
This is a very gorgeous carved shell and engraved gilt sewing kit lined with blue silk, Made in Paris, c. 1815-1820.
23points

#14

Natural stones shaped like the alphabet from A to Z, one of the coolest moments in history.
Clotilde Olyff, a Belgian Type Designer, has collected several alphabets of rocks found on the beach.
23points

#15

Reenactors dressed as Vikings gathered by a longship on a fjord, showing cool historic reenactment moments.
Norway's World Cup team photo is pretty much cool.
23points

According to Dr. Anik, autonomy is the “number-one dimension” of coolness. It refers to people who do their own thing and go against conventional expectations. 

Authenticity needs no further explanation. But as Dr. Anik clarifies, it is also about carrying yourself in a way that is true to your own personality and character.

#16

Vintage photo of a man sitting inside a hollow tree dwelling, one of the coolest moments in history.
A swagman using a hollowed gum tree as a campsite, 1880. A swagman was a transient labourer who travelled by foot from farm to farm carrying his belongings in a swag (bedroll).
The term originated in Australia in the 19th-century and was later used in New Zealand.
22points

#17

Vintage black and white portrait of Miles Davis wearing sunglasses, representing cool moments in history.
Miles Davis looking super cool!
22points

#18

Woman posing on a staircase in vintage trousers showcasing one of the coolest moments in history.
This is Helen Hulick, a burglary witness, who caused a stir in a downtown LA courtroom by wearing slacks in 1938.⁣...
⁣
Hulick was quoted in the LA Times saying, “You tell the judge I will stand on my rights. If he orders me to change into a dress I won’t do it. I like slacks. They’re comfortable.”⁣.
21points

In this context, attitude is about confidence. While it is the “rebellion against the mundane,” Dr. Anik says it should also capture “casual effortlessness.” 

Finally, association is more about attaching to someone or something that has already attained “cool” status. Dr. Anik says it is “helpful but not essential.”

#19

Elvis Presley adjusting Muhammad Ali's robe, marking one of the coolest moments in history.
Elvis adjusting the robe he gave to Muhammad Ali before Ali's fight against Joe Bugner that night., February 14, 1973. Photo by Neil Leifer. "I was the Elvis of boxing!" - Muhammad Ali.
21points

#20

Black and white photo of Roy Orbison riding a go-kart, recorded as one of the coolest moments in history.
Roy Orbison, mid-1960s, riding a home-built go-kart.
21points
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