The Dan Le Batard Show with Stugotz Screen grab: The Dan Le Batard Show with Stugotz

When it comes to interviews, Dan Le Batard has always been willing to be unconventional.

And while that strategy has often paid dividends for the Meadowlark Media co-founder, it can also blow up in his face.

That’s exactly what happened on Tuesday, as comedian Ronny Chieng joined The Dan Le Batard Show with Stugotz to promote his “The Love It Or Hate It Tour.” The interview got off to a shaky start, with Le Batard asking Chieng if he was “furious” that The Daily Show had yet to find a full-time host more than a year after Trevor Noah’s departure.

“I don’t think I’m furious. The Daily Show‘s kind of like a family,” Chieng replied. “So I can’t imagine being furious at the show, especially because they gave me my big break in America. So furious? No. Hoping we find a host, but I think we’ve been handling the show pretty well so far without Trevor.”

Despite The Daily Show correspondent clearly not agreeing with Le Batard’s premise, the former Miami Herald columnist continued to press the issue further with a series of follow-ups. Ultimately, Le Batard asked Chieng, “Can you be grateful and also want your employer to be better? Can both of those things be so?” to which Chieng sarcastically replied, “No, you cannot. You have to be just grateful.”

The awkward nature of the interview didn’t end there, with Le Batard — for reasons that remain unclear — throwing the show to video producer Taylor Vippolis, who — for reasons that also remain unclear — was on a speedboat. After asking Chieng if he had a sports question for Vippolis, it became apparent that the comedian wasn’t in on the gag.

“Um, no,” Chieng replied.

Rather than aborting the speedboat portion of the interview, Le Batard stuck with it, with Vippolis asking Chieng what the Chiefs had to do to beat the Bills this week (even though they already played last Sunday). The comedian did his best to play along, as Le Batard asked him — and Vippolis — about the state of comedy.

“Why have one bad answer when you can have two people giving bad answers?” Chieng said.

At one point, Le Batard asked Vippolis — again, his video producer and not his guest — a question about The Daily Show, to which the the producer replied, “I’m a big fan of Ronny. I gotta be honest, don’t think I’ve ever watched The Daily Show.”

Between the shaky start and the failed speedboat gag, this was already a very uncomfortable interview. And yet, it somehow got even worse, with Chieng at one point interrupting a question in an attempt the change the subject of the conversation.

“You know, you can ask me about sports. We don’t have to keep forcing these Daily Show comedy questions, man,” Chieng said. “That’s what I know you from – is from Around The Horn.”

To the best of my knowledge, Le Batard has never appeared on Around The Horn. Even if he did, it’s certainly not what he’s best known for.

Unfortunately, the interview lasted another eight minutes, which consisted of another interruption from Vippolis and a forced conversation about the state of the NBA, which neither Le Batard nor Chieng seemed to be into. By the time the interview had mercifully come to its end, Le Batard acknowledged how poorly it had gone while asking the Crazy Rich Asians star to return for a more proper interview.

“Um, sure,” Chieng replied, noncommittally.

Le Batard, co-host Jon “Stugotz” Weiner and the show’s cast of producers proceeded to spend most of the rest of the show dissecting what had gone wrong, with most agreeing that it was the opening questions that derailed the interview from the start. But even if the interview had started off on a better note, it’s hard to imagine it surviving the speedboat bit, which Chieng clearly hadn’t been made privy to beforehand.

To Le Batard’s credit, he was more than willing to not only sink into the uncomfortableness, both during the interview and after it. Such is life in this universe he’s created, in which it’s often hard to tell whether his show’s worst content is actually its best.

[The Dan Le Batard Show with Stugotz]

About Ben Axelrod

Ben Axelrod is a veteran of the sports media landscape, having most recently worked for NBC's Cleveland affiliate, WKYC. Prior to his time in Cleveland, he covered Ohio State football and the Big Ten for outlets including Cox Media Group, Bleacher Report, Scout and Rivals.