Most everyone hates getting bad news. And we all hate being the bearers of bad news even more. But New York-based comedian Jon Breaks Bad News is more than willing to share others’ tough tidings — so that they don’t have to.
As part of his rather unique career, Jon (no last name because … read on) makes around 50 calls a day, two days a week, delivering unfortunate messages to a roster of digital strangers sourced from a “bad news request” box on his website. The calls take place during one of Jon’s weekly livestreams for both his large fanbase and the receiver of bad news to hear at the same time.
But before Jon became an internet sensation, with over 1 million followers on Instagram and TikTok, the inspiration for this strange vocation came after a few drinks, while he was editing an episode of a previous failed podcast.
“I just had always had the idea of doing a sketch where I was a doctor telling somebody that they had, like, a terminal prognosis,” he explains. “And then I kind of thought, what would it be like if there was just somebody out there that did that for everybody?”
After putting out a few ads for the concept, which Jon thought would just be a funny bit between him and his friends, it quickly snowballed into an overnight internet hit, with over 30,000 members joining his newly created “Jon Breaks Bad News” Facebook page.
And so it was that Jon made his very first call in 2019, for someone who had commissioned Jon to tell her friend that she had been impregnated by said friend’s boyfriend. Other notable moments from his early career include a Facebook post announcing “mission accomplished” after being hired to tell a child that his parents were getting divorced.
“People who know my show get very excited to talk to me, even if the bad news is pretty bad,” says Jon. “I’ve had a couple of people that were like, ‘Oh, wow. You know, that does kind of suck, but it was really great talking to you’.”
Jon takes these requests for free, like the good Samaritan he doubtless is, though you can tip him and be placed on an expedited call list. Jon tells Orlando Weekly that the key to his success lies in his ability to, for the most part, remain straight-faced, even when delivering unwelcome news in bizarre and unexpected situations.
“There have been a handful of situations where I wasn’t able to hold it together anymore,” remembers Jon. “There was a guy who recently had accidentally sent his brother a video of himself pleasuring himself into a towel, and it was so embarrassing and absurd. I didn’t expect it at all, and I completely like … I just couldn’t stop laughing.”
Despite what should be a deeply unpopular role as the bearer of bad news, Jon has actually racked up a sizable and loyal fanbase on Twitch and TikTok. He says the best part of his journey to fame has been getting recognized in public by fans from other countries who want to take pictures with him and just chat.
Yet not everyone is fond of Jon, or his work. After some tense phone calls, some bad-news recipients have threatened to trace his phone number, stab him or call the cops, and he’s even been contacted by detectives more than once. Although all of these turned out to be shoot-the-messenger situations, Jon says that he has started to look over his shoulder a little bit more.
“There are tons of people that don’t like what I’m doing. There are tons of people that don’t like how I look,” he says. “You know, I get a lot of ‘get out of your mom’s basement’ comments. The funny part about that is, I’m 35, married with two kids, so I’m far from my mother’s basement.”
This very week, Jon will make calls live from the stage for the very first time right here in Florida, at Conduit on Friday. He says he’d always thought about doing a live show, and when the opportunity recently presented itself, he decided to take the plunge.
Although his wife — also his producer — won’t be able to attend the upcoming Florida shows, Jon says his best friend and co-host, Ron, will be there to provide some onstage banter in between calls. And as part of the show, wry Orlando punks The Fatties (they of “No Sex With Cops” fame) will open, whom Jon says he’s excited to be working with.
Despite jitters over trying out his act in a completely new way, Jon feels good about it. “The show is going to be extremely interactive. The crowd is going to be part of the show. The calls are going to be generated from the actual audience. So if you come to the show and you have some bad news that you want broken, I will do it for you, right then and there. We’re gonna have like a little grab box that you could put your call submission in, and then I’ll be pulling those submissions from the box throughout the show and calling them right out of the box.”
So think outside the box for your Friday night on the town, and try this show out.
(7 p.m. Friday, Sept. 19, Conduit, 6700 Aloma Ave., Winter Park, $26.91-$73.30)
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This article appears in Sept. 17-23, 2025.