Interview: ‘Conan O’Brien Must Go’ Producer On Why Conan’s a Wonder to Watch

Conan O’Brien has been entertaining television audiences for almost 40 years. He started doing so from behind the scenes as a writer on Saturday Night Live and The Simpsons then moving in front of the camera hosting late night shows almost continuously from 1993 all the way to 2021 on TBS’s Conan. Now, thanks to his new travel series the funnyman’s television journey continues across the globe.

Field producer Jason Chillemi who has worked with Conan since 1996 spoke with Awards Radar about Conan’s latest venture, Max’s Conan O’Brien Must Go. The new travel series, an extension of his popular podcast “Conan O’Brien Needs a Fan” podcast, delivers fans what they have been craving for years, O’Brien, unleashed. The series sends him out into the world to meet actual callers to his podcast, in addition to trying new things like sword fights, dancing, singing, knitting – but mainly he is making audiences laugh. Chillemil’s job was to serve as the liaison for local producers at each destination.

Conan’s earliest days of late night hosting was unlike anything else on television, silly but very smart, absurd, anything for a laugh comedy, full of awkward, self-deprecating humor. Chillemi remembered, “They just completely let the chain off and let them do whatever they wanted. There literally were no higher ups watching – like no one. They were just doing whatever they wanted.” Leaving Conan to his own devices did not strike ratings gold, but they did strike comedy gold with some of the wackiest, most out there segments ever to grace late night.

It is no wonder why Conan’s travel segments have been perhaps his most popular work to date. The chain was let off again, allowing Conan to do what he does best – this time not in a studio setting but in destinations across the globe. The first four episodes of Conan O’Brien Must Go set Conan loose in Norway, Argentina, Ireland and Thailand creating hilarious moments that are equal parts stupid, smart, and often uncomfortable. 

“My favorite thing is when we go in with a plan,” said Chillemi. “For Thailand, we knew we were going to the floating market, but we didn’t know what’s going to happen. We have permits to go there and film there, but nothing’s scripted. It’s all whatever happens and he (Conan) just goes off the cuff and he’s the best at it. We literally just gave him money, you know, none of us scouted the boat. It was just like, ‘All right, we’ll see you when you get back.’ He loves being the fish out of water and he was the fish out of water there.” 

With that money Conan quickly bought a phallic sculpture which he held in his possession for the entire boat ride through the wet market and found ways to turn it into endless laughs, unlike any other 61 year old would or could. Because as Chillemi explains, “He’ll just find something and just pick up on it and then he just goes off on it. He’s truly one of the smartest people I know and so good with people. He really is a wonder to watch.”

Conan O’Brien Must Go is an extension of O’Brien’s second podcast “Conan O’Brien Needs a Fan,” explained Chillemi, “Where he talks to fans each week, many in the United States, but some international. So we started just paying more attention, once the idea was flowing around here, we started paying more attention to the international ones. Like, ‘Oh, Norway would be a fun place to go. Let’s look for more fans from Norway.’”

And once in Norway, Conan mines humor from the most unlikely of places, including a knitting club. Like much of O’Brien’s comedic orchestra of chaos, you have to watch it to fully understand, but by the end of the segment Conan is showing off his own knitting creation, an orange French bikini and an array of jokes about it.

“We seem to be lucky. We always get that one guy, like the one in the knitting club who when Conan comments on how difficult it is to knit, is like, ‘Oh, it’s not that hard,’ adding more awkward humor to the moment. It seems things seem to work out. I don’t know if it’s just because we’ve been doing so good or just like the gods are helping us sometimes.”

For anyone expecting a hard core travel show, this is not Rick Steves or any of the other travelogs out there. Conan gives you just a different perspective on it. As he deadpanned on his much lauded episode of Hot Ones, “I love travel, and my mission is that you learn nothing about the country. My job is that you know less about the country after I’m done than when I started. You’re dumber after you see the show.”

Even if that’s Conan’s goal he still leaves viewers and even Chillemi wanting to visit the destination. “I come home from these places and I’m like, I want to take my family there.” And who wouldn’t want to visit Ireland to follow in Conan’s footsteps, tracking down the elusive U2 front man, Bono using a fake global humanitarian award as a lure?

The segment called, “Finding Bono” was Chillemi’s favorite. “It makes me cry every single time I see it. The idea on paper made me cry. It’s such a funny idea and being out there shooting it is a perfect Irish day and you can see Conan’s just having fun – he’s thinking of funny things to do. What if I pick this up and smell this leaf or lick this tree?” All in the hopes of catching one of Ireland’s most famous rockers. “And not to brag,” shared Chillemi, “but that may be the guy you’re talking to who’s handing out the humanitarian award.”

Where’s the next destination for Conan O’Brien Must Go? Chillemi did not have a definitive answer but did share, “You know, we’ve got quite a big globe, a lot more countries to see and a lot more fans that he’s talking to. Let’s go, I’m ready!”  So are we.

All four episodes of Conan O’Brien Must Go are now streaming on Max.