David Downing has the kind of face you recognize even if you can’t quite place where you’ve seen it before. Maybe it was onstage introducing a panel of city leaders, maybe in a gallery crowd at a St. Pete art opening, maybe tucked away in a corner booth of a bar where he was holding court with a group of locals. Downing has spent years shaping and selling the story of St. Petersburg—first as head of Visit St. Pete/Clearwater, later as a cultural connector and civic agitator of sorts. Now, he’s putting himself in the story in the most unexpected way: as the eccentric host of Oh Yeah?!, a scrappy, regionally flavored late-night talk show taping at the Palladium Theatre’s Side Door Cabaret.
This project is a combination of energies of two of his other passions: performing with his jazz trio and hosting his syndicated travel show, Undiscovered America TV (going into their third season).
Oh Yeah?! is being billed, with a wink, as “America’s only regional late-night talk show.” And that tagline says it all: Oh Yeah?! is absurd, playful, and deeply rooted in St. Pete’s offbeat sense of self. Picture Fallon meets public access weirdness, with a house band blasting full-throttle funk and a revolving door of local characters stepping into the spotlight.
The house band isn’t just any band either—it’s The Oh Yeah-Yeahs, better known around Tampa Bay as The Black Honkeys, a nine-piece funk machine with enough brass and swagger to blow the roof off the Palladium. When they kick in, the room doesn’t feel like a cabaret anymore. It feels like the epicenter of something that could only happen in a Gulf Coast city that’s equal parts retirement haven, art colony, and party town.
Downing himself has leaned into the role of eccentric ringleader. He’s sharp, quick with a line, and unafraid to look ridiculous if the bit demands it. This isn’t the buttoned-up tourism exec version of David Downing. This is the version that’s been waiting in the wings—part emcee, part comedian, part wide-eyed kid who can’t believe people actually showed up. His goal isn’t to chase national headlines or drag the culture wars onto stage. Instead, Oh Yeah?! keeps it light, funny, and proudly local. The only politics here are whether you say St. Pete or St. Petersburg.
The show’s cast of oddballs drives that point home. There’s Trevor Pettiford, dubbed the “Chief WTF Reporter,” and Mickey, a straight-faced “Chief of Oh Yeah Security,” along with an audience coordinator who doubles as comic relief. Together, they give the show a late-night sketch energy, equal parts chaos and chemistry.
The first tapings are rolling out this fall, and they’re free if you RSVP. That feels fitting. Oh Yeah?! isn’t trying to be exclusive—it’s trying to be a hangout, a new ritual in a city that’s always inventing ways to gather. Walk in off 2nd Avenue North, grab a seat in the Side Door, and you’re part of the show.
There’s an unspoken rebellion in what Downing is doing. St. Pete doesn’t usually get to be the stage for something like this. Late-night belongs to New York, to Los Angeles, to big networks and slick studio lots. By planting a flag in downtown St. Pete, Downing is saying the quiet part out loud: this city is strange and funny and alive, and it deserves its own spotlight.
For Downing, Oh Yeah?! is less about building a media empire and more about capturing a vibe—something messy, communal, and a little bit punk. The band plays loud, the crowd laughs hard, and the show never takes itself too seriously. Which, when you think about it, feels like the most St. Pete thing imaginable.
So if you’re lucky enough to snag a ticket and find yourself in that cabaret when the lights go up, don’t expect polish or polish-by-committee production. Expect noise. Expect funk. Expect a little chaos. And when David Downing leans into the mic with that knowing grin, expect to say what everyone else is saying these days in downtown St. Pete: Oh yeah?!
