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Being Cool Doesn’t Have An Expiration Date (30 Old School Pics)

Back in my day, if you wanted to be cool you had to own the most Teenage Mutant Ninja Turtles action figures. Apparently, while I was measuring coolness by that standard, adults were out in the world being cool in different ways.

Consequently, the photos of people from the past are often much cooler than anything I personally have to offer. Honestly, all my photos from the 80s and 90s are of me watching The Fresh Prince in a bathrobe.

Now, I spend my day in a bathrobe watching The Fresh Prince while also writing up these articles! So, a lot has changed.

Thankfully, I can escape and see how cool and interesting people once lived. The Reddit forum r/OldSchoolCool brought us some legendary pictures.

Here are the best Old School Cool photos from the past month:


1. Kids playing in the 1930s.

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2. 19 year old Lucille Ball in 1930. Today would have been her 110th birthday.

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3. My parents on their wedding day. Dad is 5’ 3”, mom is 5’ 10”.

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4. My mom in 1980 – she was 24 years old here.

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5. My parents in the late 1980’s They loved floral!

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6. Jimi Hendrix in Ringo Star’s flat. 1966.

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7. Bearded Mark Hamill in 1989.

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8. My grandma and her good friend Willie Nelson around 1980.

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9. Me 30 years ago (1991). I took 2 years of my life to travel the United States from Alaska to Texas in my old 1950 chevy truck pictured there. Some of my most fond memories were being on the road during that time in my life.

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10. Fresh Prince at the Playboy Mansion — 1992

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11. A boxing match of American sailors. 1899.

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12. Me at age 20 in 1988 with a VW Bug I bought for $50. I made a BEACH PATROL stencil out of several taped together newspapers, then painted it with a can of spray paint in my driveway.

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13. My grandma’s pink hair in the 50s.

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14. Little did I know that 38 years and a thousand projects later I would retire from the same firm. 1981.

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15. My Dad as a high school senior in the 60’s posing next to his stingray. He loves this picture and still talks lovingly about this car.

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16. RuPaul, Muggsy Bogues, Charles Barkley and Kurt Cobain at Saturday Night Live, 1993.

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17. My dad pictured in 1948 wearing the specially tailor-made coat which cost him 3 months wages. I still have the coat.

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18. Today’s the 40th birthday of the IBM PC, so here’s me in ~1994 showing my 1st-place science fair project. I matched an original IBM PC 5150 against a Macintosh Plus in a series of chess matches. The Mac won every game.

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19. Motorola engineer John Mitchell with his phone on the streets of New York. Mitchell helped develop the design for the first mobile phone. 1973.

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20. My father, a U.S. Marine, circa 1958, probably in Lebanon. Cigarette and machine gun.

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21. Senior Year Computer Class 1983 (I am the female in the pic).

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22. Young Scarlett Johansson with Destiny’s Child (1990s).

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23. My dad’s late 80s bowling team. 9 perfect games between these ragtag fellas.

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24. KISS band with their parents, 1976.

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25. My Mom Deep Underground Caving Somewhere in Missouri in 1977.

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26. My Grandma in the 60s.

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27. Just retired after 42 years as an obstetrical nurse, at the same hospital. Here I am at the start (1979) and end of my career!

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28. This is me in 1976. Getting ready for a night of partying! Corpus Christi, Tx.

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29. My wife, 1976. She still paints.

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30. Behold, my father-in-law’s senior prom photo, mid 1980s.

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h/t Reddit: r/OldSchoolCool