25 Times People Realized Previous Generations Were Way Cooler Than Us

I grew up in the 90s, where everyone seemed to just be trying to shake off the 80s. A lot of the style in both of those decades was pretty rough. Yet, every era has old school cool people. This is because being cool isn’t how you dress or what brands you rock, it’s an aura. It’s timeless. Some folks would be cool walking around in a paper sack.

It’s fun going through pics from decades past and seeing these cool people through time. Look at their posture and confidence. The look in their eyes. Man, it seems like a lot of fun to be cool.

1. My mom and dad in DC in the late 80s.


2. My uncle getting caught growing weed in the backyard. Circa 1970s.


3. My deaf father, hugging a speaker to his chest to feel the vibrations of music. Early 1970s.


4. My Uncle Billy just turned 90, so here’s him on his boat during the early 80s.


5. A friend of mine told me to post here. Me in the mid 80s.


6. My Grandmother, a white Jewish woman, looked like Barack Obama in 1962


7. My Mama circa ’83. This explains why I’m the uncoolest person ever, because she took it all! Oh and that bike? She built it.


8. When Albert Einstein met Charlie Chaplin in 1931, Einstein said, “What I admire most about your art is its universality. You do not say a word, and yet the world understands you.” “It’s true.” Replied Chaplin, “But your fame is even greater. The world admires you, when no one understands you.”


9. Me and the homies before going to see Straight Outta Compton. The tour, not the movie. Circa 1989


10. Susan Kare, famous Apple artist who designed many of the fonts, icons, and images for Apple, NeXT, Microsoft, and IBM. (1980s)


11. My dad vs me. 1984 vs 2018. Chichen Itza.


12. My grandfather lighting himself a cigarette in a double-exposure self-portrait (1950s)


13. My grandpa worked as a park ranger in Yellowstone, where he took this photo of The Three Stooges when they visited. 1969.


14. The Undertaker and his grandma – 1990s


15. My Pops finally beating Super Mario Bros. on Christmas night, 1988. The Nintendo was a present for “me and my sister”.


16. My mom and Arnold on a date in the ’70s


17. He’s impersonating his 19 year old self in Vietnam 1966


18. My Grandpa just turned 90 last Friday. Here he is in the 50s looking handsome as hell.


19. Mother helping her son through a tough level in Super Mario Land on Gameboy from 1989.


20. My mom would always talk about how she was an editor for Tiger Beat magazine when she was a teenager in the 1960’s. She would brag about spending time with the Stones and the Beatles. We always thought she was telling tall tales. Uncovered this pic cleaning out her house last week.


21. Snagged my granddad’s (86’) ski wear for my trip to slopes.


22. My dad, 1972, he didn’t know that this photo existed for almost 50 years, until someone showed him this today. Romania, Bucharest, communist era.


23.  Just how tall my Mom was. 6’2….1971.


24. Dr. Martin Luther King Jr. in Jamaica, 1967.


25. “Manhattan was a river of men flowing past my door and when I was thirsty, I drank”. Model and writer Alice Denham in a picture taken in 1962.