Meet Dan Deibert
Dan Deibert is one of the Midwest’s favorite comedians and has been cracking jokes on the stand-up comedy circuit for over 30 years, a feat that proves he’s either incredibly good or just doesn’t listen when people ask him to leave.
Born in Illinois, Dan traded cornfields for cheese curds when he moved to Wisconsin over two decades ago, settling in Waukesha with his wife of 30 years. Their household is a chaotic menagerie featuring a dog named Charlie and a cat named Stewie, the latter of whom arrived as a “temporary” guest two years ago and has since claimed squatter’s rights. Dan’s comedy career is a bit like Stewie—messy, angry at the strangest things, and has been around longer than anyone planned for.
His observational humor, which zeroes in on the things you’re already thinking but haven’t dared say out loud, once landed him as the runner-up in the National Jay Leno Comedy Challenge—a near-miss that left him with a trophy, a story, and a lifelong grudge against chin jokes.
Also, Dan has a deeply passionate hatred of wind chimes, canada geese, and glitter.
For 25 years, Dan ruled the airwaves as a radio talk show host in cities like Chicago, St. Louis, and Milwaukee, where his voice became as familiar as a car horn in traffic. Beyond his own gigs, he’s popped up on the Bob and Tom Show and Sirius XM, proving he’s the kind of guy who can talk his way into anything. He’s also hosted several TV shows, though he insists the glare of the studio lights was just his forehead reflecting his brilliance. These days, he co-hosts the Still Spinning Podcast which is the #5,322nd most listened-to podcast on Spotify—a ranking he’s oddly proud of, claiming it’s “niche enough to be cool, but not so niche that it’s just him and his mom listening.” His fans tune in for that signature style: pointing out life’s absurdities so perfectly you’ll wonder why you didn’t say it first.
When he’s not busy being marginally famous, Dan’s a man of many hobbies, most of which involve him squinting at the sky or fiddling with gadgets. He golfs, flies planes and drones like a wannabe Top Gun reject, and obsesses over Great Lakes shipping and shipwrecks. He’s taken more than one vacation to watch big ships unload iron ore. His backyard is a meteorological playground, cluttered with multiple weather stations that he checks more often than his email. Oh, and he’s an award-winning trivia host, which basically means he’s the guy you want on your pub quiz team unless the category is “How to have normal hobbies.” It’s this knack for noticing the weird details—like how your neighbor’s lawn gnome looks judgmental—that fuels his comedy.
But if you really want to see Dan light up, ask him about his meat-smoking skills. This guy treats his smoker like it’s a sacred altar, crafting BBQ sauce from scratch and bragging about his ribs like they’re auditioning for the Food Network. His neighbors in Waukesha smell hickory smoke every weekend, which Dan considers his gift to the neighborhood.
Between the comedy, the radio, the podcast, and the meat, Dan Deibert is a one-man variety show—proof that you can live in Wisconsin, talk for a living, and still have enough quirks to keep life hilariously weird. And if you’re thinking, “Man, this guy’s living my inner monologue,” well, that’s just Dan doing what he does best.