Asked this question over dinner with @czaroline and others and hey, it got a good response, so I'm trying it here.
  1. Palm reader on New Zealand TV
    This is my great uncle I think, on my Dad's side. There's loads of weird mystical stuff on that branch, but yeah, he got to go on telly and do it.
  2. Organ-grinder with monkey in NYC 🐒
    My great-great uncle when he emigrated to the US from Italy. I'm sure there have been other cool jobs but that's my favorite.
    Suggested by   @jessnobs
  3. My grandfather ran away from his dirt-poor Kentucky tobacco share cropper home at 14, and made his way to super successful entrepreneur, owner of car dealerships and grocery stores in northern Indiana, with no education beyond elementary school.
    I always thought that was cool.
    Suggested by   @gwcoffey
  4. My great-grandfather owned/ran a Dr. Pepper bottling plant in the South.
    Never drank the stuff in my life, so I feel like a disappointment. Though my dad drank like four or five cans a day of Diet Dr. P for twenty years, until he got a throat infection & cut it out, so I feel like he makes up for me.
    Suggested by   @Jazz
  5. Bootlegger!
    My great grandpa pushed alcohol for Al Capone in Chicago. They would make the moonshine in their bathtub. Once the house caught on fire and he let the firefighters fill their hoses with alcohol as a thank you.
    Suggested by   @mackenzieo
  6. Revolutionary War Heroine
    Look up Emily Geiger. She was like my 5th great aunt.
    Suggested by   @classyAF
  7. Paratrooper into Normandy during WWII
    My grandpa was in the army (101st airborne division) and was one of the paratroopers that landed on the beach in Normandy, France!
    Suggested by   @michellejennifer
  8. Slave. I researched my family tree online and came across a guy that was listed as a slave in 1800's Bethnal Green, London.
    Suggested by   @LissyLis