notbob1959 on October 30, 2025 4:06 am OP is a bot. [Original post.](/r/OldSchoolCool/comments/1kg0gan/i_never_met_my_grandpa_but_he_looked_cool_as_hell/)
punkassjim on October 30, 2025 4:24 am Maybe I’m just old, but I no longer automatically think “That guy must be super cool!” when I see a smiling dude in a trilby holding a rifle. ¯\_(ツ)_/¯
CaptainBathrobe on October 30, 2025 4:38 am Man knew how to wear a hat. I keep trying to wear mine on my ass, and it never works.
11 Comments
With the BB King on deck too! 😎
that man looked great in hats!
Okay I approved! 🤠
OP is a bot. [Original post.](/r/OldSchoolCool/comments/1kg0gan/i_never_met_my_grandpa_but_he_looked_cool_as_hell/)
The ladies think he’s cool too!
Pimpin ain’t easy.
Looks like Marcus Garvey wow
Maybe I’m just old, but I no longer automatically think “That guy must be super cool!” when I see a smiling dude in a trilby holding a rifle.
¯\_(ツ)_/¯
Man knew how to wear a hat.
I keep trying to wear mine on my ass, and it never works.
Papa was a rollingstone
Wow