How ‘My Next Guest With David Letterman’ EPs Navigated Ukrainian War Zone for President Zelenskyy Interview

While “My Next Guest With David Letterman” executive producers had previously pulled off intimate sit-downs with culture-makers like Barack Obama, Malala Yousafzai and Cardi B, producing an in-depth conversation in a Ukrainian war zone was certainly not in their repertoire before pursuing an interview with Ukraine President Volodymyr Zelenskyy.

The idea to interview Zelenskyy started with producer Tommy Alter, and scored Letterman’s immediate enthusiasm as the host told EP Tom Keaney, “this is the only thing I want to do.”

“I think Dave’s immediate reaction was probably generated by the fact that this is a world event that’s happening in real time,” EP and Imagine president Justin Wilkes told TheWrap, adding that it was “still fairly early days in the war.” “He’s one of the most interesting people on the planet right now, and wouldn’t it be interesting to go talk to him and see if we could actually pull that off?”

Determined to lock down a conversation with Zelenskyy, who was not readily accessible at that point in the conflict and had only done several short-form interviews with journalists including Christiane Amanpour, the producing team began sorting through logistical arrangements, starting with getting in touch with the president’s office.

Luckily, Imagine, the production company behind “My Next Guest With David Letterman,” reached out to chef José Andrés, who they had worked with on recent documentary “We Feed People,” as his nonprofit World Central Kitchen mobilized in Kyiv. Almost instantaneously, Andrés responded that he could get a letter from Letterman to Zelenskyy’s office with the request.

“It was a very typical Dave letter that instantly got the president’s attention, I think very quickly, both because the president, as a former comedian, was very familiar with Dave and looked up to Dave, but also understood what this platform can be as an opportunity to really get his message and the message of the Ukrainian people out there,” Wilkes said. “He responded very quickly.”

“I think an appeal from a comedian to another comedian to have a conversation — that was sort of the gist of it,” Keaney added.

From there, the team worked with the president’s office to learn about how to safely move through the country, as well as secure the location for the interview — which took place safely underground in a Kyiv Metro Station, where Zelenskyy had previously hosted conversations with visiting dignitaries.

“We spent a good month just calling folks and getting a sense of what people were doing on the ground, what kind of scenes that we could shoot that seemed appropriate, but also logistically was possible with the size crew that we had, which was very small,” director and EP Michael Steed told TheWrap. “Finding the local crew that could work with us was pretty standard in that sense, but it always had that understanding that we were headed to a place that is in the middle of a war.”

Leading up to the team’s journey to Kyiv, which required a flight to Warsaw, a drive to a small town in Poland called Przemysl and a 14-hour train to Kyiv, the producers downloaded an app that would notify users when a missile is coming, which had become commonplace for Ukraine citizens.

“There hadn’t been a significant missile strike in Kyiv for quite some time at that point… And then there’s a significant missile strike that happens within a week of of the departure date,” Wilkes said. “There was a real moment there where everybody, Dave included, got on a call to talk about the safety and what do we all think about this.”

Despite new obstacles and reminders of inevitable dangers, the team never wavered in their decision to head to the war zone as they knew Zelenskyy’s commitment to the appointment remained steadfast.

“While it’s it’s uncomfortable and disconcerting, it’s nothing compared to what they’re experiencing on the ground,” Wilkes continued. “If the Ukrainian people in the president’s office are projecting that degree of resilience, then you’re going to rise to the challenge to meet them.”

In the special, which was nominated for an Emmy in the outstanding hosted nonfiction series or special category, Letterman stopped at a local comedy club, a discovery the producing team credits to co-executive producer Razan Ghalayini, in an effort to dig into Zelenskyy’s comedic roots.

“That, for us, was a very important field trip to actually inject levity by going and finding these comedians who are doing incredibly dark humor, in some cases, in the face of great adversity,” Keaney said. “We really wanted to talk to people who were in comedy now, particularly in a wartime setting.”

While the EPs admitted they weren’t certain how Zelenskyy would react to a discussion about comedy as a head of state in a war, they noted that the President “opened the door” to the topics and “allowed himself moments of real, lighthearted levity” as he pointed out the importance of maintaining perspective in the midst of a horrible situation.

“He has to wrestle with [it] on the daily because he comes from a comedy background, but he knows the seriousness of his situation — he’s both of those men; he’s both of those people,” Steed said. “To be able tap into that, and then have a president who comes from that background was really an amazing opportunity, and rare.”

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