eBaumsWorld: Funny Videos, Pictures, Soundboards and Jokes
Spicy Funny Galleries Funny Videos Games Time Wasters Internet Classics
eBaumsWorld: Funny Videos, Pictures, Soundboards and Jokes
  • Spicy
  • Funny Galleries
  • Funny Videos
  • Games
  • Time Wasters
  • Internet Classics
SpicyFunny GalleriesFunny VideosGamesTime WastersInternet Classics
  • 1 - 10
  • 11 - 20
  • 21 - 23

23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

No matter how cool you are, your grandpa was probably cooler.

By Carly Tennes

Published 7 months ago in Wow

Long before they earned the ever-coveted titles of "dad" and "grandpa," our paternal figures were way cooler than any of us realize, sporting three-piece suits, kicking their loafers on the hood of old-timey vehicles, and even piloting airplanes. Don't believe it? Just take a look back at some of the most iconic photos that have passed down from generation to generation. 


From a tough-as-nails biker to the sharpest-dressed man on Michigan Avenue, here are 23 sepia-faded snaps of our dads and grandpas from the '20s and '30s that prove they were always the coolest guys around. 

  • 1

    “My great grandpa in the 1920’s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 2

    “My Great Grandpa looking fly in the 20s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 3

    “My grandpa played at speakeasies in the 20s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 4

    “My Great-Grandpa 1920s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 5

    “Grandpa was ripped - 1920’s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 6

    “Great grandpa, going for a bike ride in a three piece suit (1920s).”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 7

    "My Dad's late 1920-30's."

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 8

    “My Grandpa in the 30s looking cooler than I could ever hope to be.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 9

    “My grandfather in the 1930s. An Italian immigrant and worked in the coal mines of western Pennsylvania.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 10

    “My grandfather circa 1930s beginning a line of three generations of career aviators. I'm continuing the tradition as a UH60M pilot.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 11

    “My Grandpa 1930’s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 12

    “My grandad in 1930 with his motorcycle, which still survives in my garage.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 13

    “My grandpa circa 1930s in the US Navy.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 14

    “My grandpa. Guessing late 30s-early 40s. Dude looked like he enjoyed a good time.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 15

    “My Grandpa, 1930s Chicago.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 16

    "My grandpa in his early 20s, mid 40s or early 50s."

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 17

    “My grandpa’s got game, c. late 1940’s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 18

    “My Grandpa on his motorcycle. 1940s.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 19

    “My Dad 1940s (Lower Right with the Helmet On).”


    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 20

    “T-6 Trainer my father flew in WW2 as part of his pilot training.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 21

    “Today is my dad's 97th birthday. This was always my favorite picture of him. (Late 40s).”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 22

    “My Dad. I’m guessing taken in the late 40s. He would have been 90 today.”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

  • 23

    “My grandpa at age 16 next to his uncle’s car [Late 1940s].”

    23 Vintage Photos That Show Dads and Grandpas Who Were Much Cooler Than Us

Categories:

Wow History Trending

Tags:

1920s 1930s dad grandpa throwback father's day
Scroll Down For More


Most Popular

The 21 Funniest Tweets of the Week

The 21 Funniest Tweets of the Week

Saturday Morning Randomness: 39 Fun Photos to Fuel Your Morning

Saturday Morning Randomness: 39 Fun Photos to Fuel Your Morning

31 Cursed Pics to Get a Little Weird With It

31 Cursed Pics to Get a Little Weird With It


  • About Us
  • Privacy
  • Terms
  • DMCA
  • Contact

If you are the original creator of material featured on this website and want it removed, please contact the webmaster

Copyright© 1998-2025 Literally Media