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We started The Pickup because we wanted to cover Tulsa from the ground up. This is a polite way of saying that we were sick of hearing about the same “40 under 40” corporate rockstar-type people in local media year after year after year. Tulsa’s much weirder than that!
And so as we started covering Tulsa from a new perspective, new characters began to emerge. We met pranksters, heroes, hucksters, visionaries and innovators. Some are our neighbors, people who live in Tulsa’s modern day. Others are figures of local lore.
So here are our favorite characters we met along our new adventure this year, from the new-to-us to the purely fictitious. We even threw in one or two characters whose very existence seems to blur the line between these two modes of classification, depending, I suppose, on how you think about artificial intelligence. Enjoy, and we'll see you in 2026! —Matt Carney
The star of one of Russ Cobb’s earliest pieces for The Pickup, Sadie James emerged as a gun-toting, shit-talking barwoman who managed Tulsa’s infamous “Bucket of Blood” (which was definitely not a brothel, according to her) in the early 1900s. Russ Cobb went looking for her; you can read that story here. —Z.B. Reeves
We didn’t think it was possible to loathe the Cry Baby Hill sculpture any more than we already did. Then we discovered that its “creator” uses AI not just to “design” his “art” but also to “write” "project" “proposals” like the one he submitted to the City of Tulsa. Tulsa paid a quarter of a million dollars to a dude who lets a LLM do his work for him. I still feel like I’m going insane when I think about this story. —Alicia Chesser
Buried pretty deep within John Paul Brammer’s big story for us about Oklahoma City’s overly ambitious Legends Tower development was a curious bit of AI fakery. The website for the fishy nonprofit Aspiring Anew Generation featured some hands with too many fingers and claimed it was led by Dr. Jessica Stanford, a presumably real person whose about page “read like the kind of literature state media might proliferate on behalf of a despot it didn’t actually know much about.”
We’re still not sure if Dr. Stanford is real or not because the whole thing “stank of ChatGPT,” as Brammer concisely put it. She is gestured toward in a YouTube video of an OKC city council meeting, but doesn’t appear onscreen. In that sense, Dr. Stanford is perhaps, of all these characters, the one most direct stand-in for the feeling of being alive in 2025, as AI slop drives us each slightly insane. —Matt Carney
A true outsider artist, Bill Rabon has fascinated me for a long time, so it was great to see The Lowdown nod to him in the name of its own anti-hero. Revisiting his life and work brought up so much of the Tulsa that This Land documented so well: the “Little Bohemia” that once thrived south of downtown, the unconventional genius of Gaylord Oscar Herron and Dan Mayo, the world that made JJ Cale and Joe Brainard. His smile, in the This Land film we linked in this story, sticks with me. —Alicia Chesser
One of the spookiest, most quietly intimidating characters in Tulsa lore, Condon emerged from Russ Cobb’s Nasty Newspapers story with a maniacal focus that could rival Michael Myers. The managing editor of the Tulsa World saw enemies to the white American way of life everywhere he looked, and is believed to be responsible for one of the paper’s most notorious editorials that presaged the 1921 Race Massacre. Cobb describes him as thus:
Condon was an odd mixture of journalist, prankster, and vigilante. He doxxed people who did not buy Liberty Bonds, published a faux police report about himself, and participated in a torture session of suspected Wobblies.
The spookiest thing about Condon? After his days torturing socialists were done he became a “genial radio host,” known as “Mr. Oklahoma News.” —Matt Carney
I’m sorry, but I just can’t look away from this guy. He’s like a Tim Robinson character: despicable to the point where his presence alone offends normal company. Roll the footage:
My date showed up peacocking, in a silk shirt, with dice-themed rings and necklaces, and a very expensive-looking cowboy hat (odd, since he was from the east coast). He rattled off some obviously rehearsed flirty lines and some frankly odd beliefs about gender roles, then—when I was ready to bolt for the exit—whipped out a pack of gold playing cards.
The gold playing cards is the detail that sends this one to the moon for me. Who carries gold playing cards? If you know this guy, please email me at matt@thepickup.com because I want to assign a 9,000-word profile on him. —Matt Carney
In 1941, Salomia Williams (Spunk) and Cleveola Kemp (Punk) opened the Down Beat Ballroom, an undersung jazz club which hosted the likes of Louis Armstrong and Ella Fitzgerald before being destroyed in a fire. Oak Tree Books’ Sean Stanford brought their previously unseen story to us earlier this year; you can read that here. —Z.B. Reeves
Continuing on our theme of characters who may not even exist — we found ourselves in a dilemma this fall when we received a bogus pitch from a suspect writer who we quickly discovered had submitted AI-generated stories to other publications, including The Cut, Architectural Digest and The Guardian. For a peek into our AI hellscape future, you should read her pitch to us about the Tulsa Sound. —Matt Carney
Kathryn Parkman’s terrific story about Tulsa’s warring pinball leagues gave us some memorable quotes from all parties. But Lucas DeWoody and Rita D’LaVane emerged within the story as Tulsa trailblazers, fighting for inclusivity in a space whose gender politics is perhaps more fraught than you would think. —Matt Carney
There were many memorable characters in Becky Carman’s dispatch from the monster truck rally—Bigfoot, Mega Wrex, 5-Alarm, Tiger Shark, Boneshaker, Skelesaurus, Arctigon—but for some reason Gunkster captured our imaginations the most here at The Pickup HQ. Who is “he” and was “he” bullied as a child? What’s with the gunk? What’s the backstory here?
“Would I go see more monster trucks, knowing what I know now?” Becky asked. “Man, probably. Even with all the quibbles, I still found myself invested, earnestly muttering things like, ‘Is Tiger Shark having an off day? He really shit the bed in the Wheelies,’ and, ‘Why does Bigfoot smell worse than a truck named Gunkster?’ —Alicia Chesser
It turns out that Phyllis Van Deusen has a major following. We learned this after publishing Megan Shepherd’s personal essay about going to see the Saplupa iridologist, who’s operated the Rock Creek Herb Shop for decades. The story caught major tread on our Instagram account, where an outpouring of responses sang Phyllis’s praises. —Matt Carney
We adored this interview with one of Tulsa’s funniest working comedians and the photos that were shot on location at Thunderwof’s family ranch in Turley. Come for the extremely wholesome horse photos, stay for the comparisons between being a cowboy and doing stand-up. —Matt Carney
I find myself randomly thinking about this woman now and then, especially when I’m feeling sorry for myself and remember that she’s out there finding people’s lost kids, digging through trash, hunting down catfishers (and worse). ”Krista Pavey has a black eye” was one of the best opening lines of any story we published this year—especially since it turned out to be from botox rather than some dude’s fist in her face. I’m pretty into stories about people who, when they find their thing, just run full force with it. With her Black & Red notebooks and relentless research and noir-vibey office, Tulsa’s premier female private detective is one of those people. —Alicia Chesser
Max Comer was one of my first big assignments here at The Pickup. His rise to fame as a Lord Of The Rings influencer (he says he’s not one; I disagree) on Instagram and TikTok has been a surprise to everyone, including himself. Read my profile of him here. —Z.B. Reeves
Henry Roanhorse Gray took on a major assignment early in the year when he immersed himself within Tulsa’s queer gun culture. There he linked up with the teaching duo of Natalie and Billie, who come from different schools of thought on guns and self-defense only to find agreement when it comes to protecting the trans community. By teaching traditionally marginalized people to defend themselves, they’re flipping the script on Oklahoma’s robust subculture around the second amendment. —Matt Carney
As shocking as it was to see an American made Pope this year, it was even more shocking to learn that Leo XIV had a Tulsa connection. From 1999 to 2001 he was reportedly “down here frequently for meetings” as a member of the Cascia Hall Board of Directors. I still need to know if we get some sort of plenary indulgence from walking around the 21st and Utica area after he did, and also if anyone told him about the psychedelics. —Alicia Chesser
We’re wishing the best for Tulsa’s most famous troubled youth. —Matt Carney
Our eternal Employee of the Month, Lady the Shih-Tzu is a powerhouse of efficiency, productivity, and forward thinking. Specifically, her KPQs (Kibbles Per Quarter) this year were through the roof. Enjoy a sweet little story about Lady here. —Z.B. Reeves
