Jason Jones is one of those lucky guys who managed to make a career out of seeing the world, with cameras in tow. For nearly a decade he worked as a correspondent for Jon Stewart’s satire news program The Daily Show, venturing to distant lands like Russia and India to interview foreign leaders. Coming from a sketch comedy background, interviewing politicians was not a career that Jones had anticipated, but one that he welcomed.
“No question it was a pretty great perk getting to travel with the show to places I had never been,” Jones admitted over a pilsner with Men’s Journal at the Arlo Nomad. “They weren’t the normal experiences that most people have on the road either. I was riding ox carts to find polling stations in India, scouting for black market interviews in Russia, and being followed by cars in Iran.”
The perks of working at The Daily Show went beyond interesting travel though; it also meant Jones got to work alongside his wife and fellow correspondent Samantha Bee. They both left the program in 2015, and they’ve since created their own series for TBS called The Detour, a relentless comedy about a road-tripping family based on their own experiences, which stars Jones as patriarch Nate Parker.
Now with the show entering its third season, Jones has spent the better part of three years reminiscing about the adventures that changed his life for the better. Here the comedian remembers his first out-of-country trip with partner-in-crime Bee, and how it helped prove that she was the one.
Men’s Journal: Did you always love traveling and road trips?
Jason Jones: I didn’t get on an airplane until I was 15. My mother bought me a ticket to Calgary where my aunt was living so that I could go skiing out there. I was like, “What is this?” I was completely blown away by the experience. I didn’t really start going on trips until I got out of college and was working as a waiter. I had this buddy who loved to go on trips. He asked me if I wanted to go to Mexico for three months. In my head that sounded like too long to be gone from the real world. But I was young and I went for it. I am so grateful that I did it. I started to really crave those kinds of trips, and I would take two weeks here or a month there to go somewhere different. I went to places like Guatemala and Belize, where the money would go a little farther.
MJ: Since The Detour is about family vacations, how did your first big trip with Samantha go?
JJ: [Laughs] It was a memorable experience for sure. I took Sam to Cuba for our first big trip. We had started officially dating in April, even though I had known her before that, and her birthday was in October. On her birthday I pulled out a pair of tickets and she was a little confused at the beginning because there weren’t any hotel reservations to match. She said, “Oh great, where are we staying?” I think at first she was expecting us to be part of some cushy charter where everything was taken care of, but it was the exact opposite.
MJ: So where did you end up staying?
JJ: I had a rough idea for each night. I remember when we first landed we took a sketchy taxi or bus, I can’t remember, it was something shitty for sure, and went up to the sand strip Varadero. On the way we passed all the beach resorts because we weren’t staying there, we were staying at the campground at the very end. I had my tent with me. So we set it up and it was actually amazing.
MJ: How was it to travel around Cuba at that time?
JJ: It was pretty incredible. The coolest thing that we did was a hike to Fidel Castro’s old revolutionary headquarters, Comandancia de La Plata, way down in the South of the island. It was about a three-hour hike up the mountains, but absolutely worth it see this tree fort that he basically took over the country with. They didn’t let us bring any cameras at the time because according to the guards, “He might use it again.” They were especially proud of this trapdoor that Fidel had built in there, where a slide would slide would carry him out into a ravine and out to the ocean, where boats would pick him up.
MJ: Did you guys face any challenges being in an unfamiliar country?
JJ: Oh yes. There was one day that we waited for a train at a train station for six hours before someone came up to us and told us that there was no train coming. Apparently, the trains were going to a station right near there. Then there was a day I got brutal diarrhea. We were staying at this tiny little place with a bathroom that didn’t have a door. She was in the other room and I just exploded. I remember saying, “You heard that right?” She was like, “Yep.” I mean I really got it all out in the open pretty early there. I guess you could say that was a good thing in the end.
MJ: In the end, how do you think it panned out?
JJ: I don’t know if she loved it, but she liked me enough to put up with it. It’s fun to think back on it. Going to a beach in Jamaica and drinking beers is fine, but you don’t remember those trips. You remember the moments that went wrong and you got through it together. There is nothing that tells you that you are going to be with someone forever like an intense trip where you are out of your comfort zone. Those are the stories that stay with you and bring you closer. Especially when shit goes wrong.