EXCLUSIVE: ‘Toga kid at center of 10-year HBO rabbit hole
Meet Hatsational’s legendary 🎩 'overly stylish boy' from 2017 — who didn’t know he was becoming famous until Friday, when his 'tweenage' pic landed on HBO.
“You need to watch this.”
A hot tip with a wild-looking link?
Nothing makes me happier.
I lied.
It makes me happiest when the hot tip leads me not only to a juicy Saratoga-in-the-news story but then — the “little Art Deco bastard” at the center of it all takes my phone call.
If you haven’t yet heard about Hatsational’s now-legendary “evil hat boy” making audiences laugh across the country (although, he himself just found out) buckle up.
And then watch it all go down — tonight; you’re snowed-in, right? — on HBO.
— Abby
EXCLUSIVE REVEAL:
The kid from Saratoga who inspired this comedian for 10 years but never knew it.
Until his ‘tweenage’ pic landed on HBO.
What if you woke up to discover that in some circles, you’re famous.
And you never knew.
Born-and-raised Saratogian Rande Jackson woke up Saturday to exactly that scenario — and to make it even potentially-cringier, it all stemmed from an incident that happened when he was just a teenager.
A fabulous teenager, that is, dressed to the nines for his job at Hatsational during pre-pandemic track season in Saratoga Springs.
Validation? Never heard of her. He oozed confidence so memorably that when a Skidmore grad/stand-up comedian named Chris Fleming came in and met the old soul rocking a derby, he would never forget it. His shtick about the “little Art Deco bastard” in the hat grew and grew and then — almost 10 years later — streamed on HBO.

“It is me,” said Jackson, now 25 and living in Indianapolis, when he answered the phone earlier today. I had just watched him get positively roasted — mouthful-of-braces pic and all — on HBO’s newest hot stand-up comedy special, Chris Fleming: Live at the Palace, which dropped Friday.
“Girl, this is like the craziest thing that’s ever happened to me in my life,” he says. “And I keep telling everybody that I know that I swear this would only happen to me.”
The fact that this story could happen at all in a post-social media world is pretty wild, especially since the purple jumpsuit-wearing cheddar enthusiast with the mic even puts an old Instagram post up on the screen in front of his wildly-cheering audience.
To give you a feel for Fleming’s comedy, here’s a taste:
“Something you’ve got to know about Hatsational: Time doesn’t flow there the way you and I are used to time flowing,” Fleming tells a roaring Chicago audience. “It’s ruled over by a 14-year-old boy. And he claims status. He’s decked out in formal wear, and I’m not talking black tie, no. I’m talking Jazz Age tycoon formal. And he’s very quiet, but not because he’s shy — because he doesn’t respect you enough to raise the volume of his voice.”

Just reading it doesn’t do it justice. Which is perhaps why, when Jackson first heard of it, he was left hanging until he could get home and watch for himself.
“I got a DM from somebody I went to high school with, but I went to work and was busy,” Jackson says. “They didn’t give me any details, so I was sort of anxious all day. I’m like, ‘oh my God, what could this possibly be about?’ But then I watched it and I died. It was so funny.”
Jackson, who worked at Hatsational from 2015 to 2020, then called up his old boss, owner Joyce Locks.
“She’s the true icon of Saratoga, by the way,” he says. “I told her about it, and when she called me back they [Joyce and her husband, Roger] were just on the floor; they were in tears. They thought it was the funniest thing ever. She was like, ‘He really got your mannerisms down.’”
So Fleming was accurate?
“I must say he was very accurate,” Jackson says, laughing.
And has Jackson connected with the man who made him famous? You betcha. He DMed him next and said, “I’m the evil hat boy.”
“He was like, ‘oh my God, you’re the star of the show,’” Jackson says. “You’ve become such a character over the last couple years.’ Super funny. I mean, luckily for him I’ve been such a good sport!”
Watch it all go down now on HBO max.
📌 ICYMI…
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2 hot openings, 1 winter-specific MO
IN BRIEF
Also at the mic
Saratoga’s own Noel McLaren and Zac Denham’s new podcast — Off Track Talk — dropped its first episode today, with a small business deep dive with Saratoga Broadway’s Deli owner Daniel Chessare. (New here? Catch up on some recent Facebook messiness here.) Coming up in future eps: Trinity Mouzon Wofford will pull on your heartstrings re: her memories of the Mouzon House (currently up for sale), and Jenna Rochelle Hote will bring the glam. The Saratoga mom was a contestant on Season 20 of America’s Next Model. The reality show is enjoying a major moment thanks to the new Netflix docu-series Reality Check.
Stamina time
“Sammy can’t drive 55 – and he lives life to the max, too!” This Threads post by an old friend of mine from the west coast piqued my interest — Sammy Hagar, of course, famously wrote his “I Can’t Drive 55” mega-hit after an incident right here on our little slice of the Northway, so I perked up at the reference. Turns out, Hagar, now 78 if you can believe it, has a new line of supplements. (What is happening right now??) “As I got older, I wasn’t interested in slowing down or masking fatigue,” Hagar said in a release about his longevity vitamins. Hey, the man’s almost 80 and has a sell-out residency in Las Vegas. I know, now your interest is piqued, too. Sold locally at Walmart and on Amazon.
SPRING THINGS
Women’s Expo alert
If Ashley Salvadore calls it her “FAVORITE event of the YEAR” it must be good! Tickets to this weekend’s event at the Albany Marriott run only $10 bucks, and the buzz is buzzing. “Grab your girls,” Salvadore continues in her viral post. “Call your mom. Text the group chat! This is THE thing to do in March!” She touts the shopping, free samples, networking, glam and giveaways.
It’s Indian Ladder time
The “sweetest sign of spring”? Maple, and Indian Ladder’s got it. The activity-packed farm reopens for the season on Thursday — and they’ve got some fancy renovations to show off. They’ve also got Maple Fest March 14 and 15, the first Vinyl Brunch March 22, and the first Baby Animal Day April 3.
PSA
Your vote counts!
Tomorrow’s the last day final voting day for the Capital Region’s biggest “Best of” contest, put on by the Times Union. Make it count for Saratoga’s local businesses!!



