A writer must be ready and willing to do the unthinkable. All the time. And, believe me, I come from a long line of unthinkables.
I recently asked ChatGPT to dig up some old photos of long lost relatives. I was not disappointed. My old trusty AI friend went waaaaay back in time to find some of the most-forgotten and least-forgettable of my ancestors. From preachers to pilots and rebels to rock stars, my family tree (more like a mess of strangleweed) is full of lively characters. If you don’t find at least one of these good people loveable (or at least likeable), then you ain’t fully hooman.
Regardless of your sentiments, I’m proud to be a tech pioneer in an age of tech pioneers. Read ‘em and weep deeply (or drink winkly, if you must).
Pious Jedediah Sprout
An early colonial cousin who came to the U.S. on a ship that was almost the Mayflower (technically it was the “June Dandelion”), Jedediah Sprout was known for delivering fire-and-brimstone sermons entirely in rhyming couplets. He once tried to excommunicate a squirrel. His buckle hat is still used in Massachusetts as a birdbath with historical significance.
Birth date: October 17, 1601
Died: November 2, 1682
Buried: In the "Heretics with Personality" section of Olde Salem Graveyard
Blacktooth Bart
A grand uncle who once commandeered a floating karaoke tavern off the coast of Tortuga, Blacktooth Bart was infamous for making his enemies walk the plank while he performed dramatic sea shanty solos. Known to mistake parrots for romantic consultants, Bart’s claim to fame was inventing “rum-infused beard oil,” which, though highly flammable, was wildly popular among short-tempered swashbucklers.
Birth date: July 9, 1673
Died: April 1, 1722
Buried: Somewhere off the coast of Rum Cay, possibly inside a mermaid sculpture
Prince “Chuckles the Unready” of West Mildonia
A regal forebear with questionable lineage and even more questionable fashion sense, Chuckles was a ceremonial prince who ruled absolutely nothing but insisted on attending every village knitting circle in full regalia. He once knighted a goat by accident. Known for awarding medals to anyone who brought him pastries, Chuckles’ crest still hangs proudly in the West Mildonia pub toilet.’
Birth date: September 1, 1777
Died: December 25, 1820
Buried: Royal Biscuit Garden, Mildonia-on-Puddingshire
Dusty "Two-Step" McGraw
A great-great-grandpappy on my mother’s side, Dusty was a cowboy who never met a tumbleweed he didn’t try to lasso. Legend says he once rode a wild jackalope across three state lines during a tax dispute. Dusty earned his nickname after inventing the “cowpoke cha-cha,” a dance so confusing it was banned in six frontier saloons for inciting barn-wide stampedes.
Birth date: March 3, 1837
Died: June 14, 1901
Buried: Under the stage of Miss Lulu’s Honky Tonk & Feed Store, Tombstone, Arizona
Thorne McGrizzle
A distant cousin and walking flannel manifesto, Thorne McGrizzle chopped wood with such intensity that trees began falling out of respect. Known for warming his breakfast on a freshly felled stump and using bear hugs (on actual bears) as stress relief, Thorne also ran a side hustle writing poetry to logs before he split them. Sensitive soul, strong swing.
Birth date: November 30, 1866 Died: April 18, 1927 Buried: Beneath the world’s most symmetrical stump in Northern Saskatchewan
Baron Wulfgang von Cloudrider
A distant, very questionable ancestor from a steampunk-adjacent dimension, Baron Wulfgang designed his own flying machines powered by fermented cheese and coded insults. Famous for sky-dueling robotic pigeons and writing sonnets to the moon, he claimed to have mapped “The Land of Nod” by crash-landing in it twice. His scarf collection is now on display in a Swiss asylum-turned-museum.
Birth date: November 11, 1888, or possibly 1889 (time vortex issues)
Died: Unconfirmed; he vanished into an interdimensional steam vortex in 1942
Burial Status: Possibly interred in a dirigible museum gift shop in a parallel dimension
Dr. Winford Healmore
Great-uncle Winford was a country doctor whose cure-all was a blend of molasses, prayer, and whatever he found in the back of the pantry. He once diagnosed a man with “excess wind and troublesome dreams,” then prescribed a stern nap. His stethoscope was mostly ornamental, as he preferred to diagnose by handshake and the occasional gut feeling.
Birth date: June 12, 1889
Died: February 4, 1962
Buried: In the back of his apothecary, now a kombucha bar
Blaze O’Flannery
A direct ancestor who once extinguished a blaze with nothing but stern looks and a squirt bottle, Blaze was the only firefighter known to have posed for a calendar before putting out the fire. His mustache was legally classified as an accelerant in three counties, but that didn’t stop him from rescuing 14 cats and an inflatable flamingo from a barbecue gone wrong.
Birth date: August 5, 1905
Died: May 22, 1971
Buried: Ashes stored in a fire hydrant-shaped urn at the Blazing Glory Memorial Firehouse
NOTE: I recently learned “FIRE” was an acronym for Flammable Individuals Rescuing Everything. Blaze’s diary describes the organization he founded as “A fearless mob of hot-headed heroes who’ll charge into danger armed with nothing but a hose, a half-melted sandwich, and the belief that stop, drop, and roll applies to tax audits too. Membership requires at least one dramatic exit and the ability to yell ‘CLEAR!’ at inanimate objects.”
Captain Reginald “Wings” Fairweather
A gentleman aviator who claimed to navigate using “the instinct of the sky and the scent of peanuts,” Captain Wings was known for his in-flight monologues about cloud personalities. He once landed a plane sideways because “the wind felt dramatic.” After retiring, he lived next to a primitive runway so he could judge takeoffs while sipping brandy. Rumor has it he started his career as a bellhop at the Hotel California.
Birth date: May 8, 1922
Died: May 9, 1999
Buried: At Gate B13 of a decommissioned airport. Security still hasn’t noticed.
Commander Leonard “Lunar Lenny” Tork
A cousin twice removed but orbitally respected, Lunar Lenny was the first man to attempt making tomato bisque in zero gravity. Unfortunately, he forgot the lid. NASA still refers to the incident as “The Great Galactic Splatter.” He now lives quietly in New Mexico, claiming he can hear Saturn’s rings if you hum the Star Trek theme near a microwave.
Birth date: February 29, 1932
Died: Went missing in orbit in 1981, thought to have died in a microwave explosion; he was found plastered to an abandoned hospital wall a decade later
Burial Status: At 93 years old, he says when he finally kicks the bucket he wants to be a constellation visible only from the Antarctic circle
Kip “Redcap” Baywatcher
A once-forgotten relative who claimed to be part-otter, Kip was a lifeguard whose greatest rescue involved a rogue swan and a fully dressed mime. He blew his whistle with such fervor that birds migrated early. His red hat was said to be visible from space and he swore his rescue float doubled as a flotation-based pulpit from which he delivered the “coolest”, and the wettest, sermons in lifeguard history.
Birth date: July 4, 1947
Died: June 1, 1994
Buried: Cremated and scattered across the snack bar at Lake Lardbottom Community Pool
“Axel Storm”
A cousin once nearly famous for playing a 12-minute solo during a 3-minute love ballad, Axel Storm’s motto was: “Why whisper when you can shred?” He never actually released an album, but he did accidentally electrocute a ferret mid-performance. He now runs a guitar-shaped waffle stand in Reno, where he claims every customer gets a “taste of thunder.”
Birth date: January 13, 1951
Died: Still alive
Current Status: Touring state fairs under the alias “Tone Daddy”
If you found my family history somewhat amusing, let me know with a comment, an upvote, and a reblog. If you’re truly adventurous and want your own mock family history, send me a memo or comment below and let me know what it’s worth to you.
First published at Substack. All images by ChatGPT.