Sean Penn on Meeting Assad, His Rumored Jamal Khashoggi Documentary and New "Silly-Ass Novel"

Andrea Klerides/Michael Priest Photography
Paul Theroux (left) and Sean Penn

Throughout the hourlong conversation Tuesday night, the actor-director and 'Bob Honey Sings Jimmy Crack Corn' author shared his sources of inspiration (one being the Parkland survivors) and discussed his "reputation for self-seriousness."

In a conversation that was as exuberant as his latest novel, Sean Penn took a crowd of New Yorkers at the 92nd Street Y through his journey as a writer — which apparently began when he was just 9 years old — while also indulging author Paul Theroux's questions about El Chapo, Donald Trump and Jamal Khashoggi.

The latter figure, a Saudi journalist and Washington Post columnist, was killed in 2018 when he visited Saudi Arabia's consulate in Turkey to obtain the required paperwork to get married. Penn believes that Khashoggi was "murdered by the crown prince of Saudi Arabia [Mohammed bin Salman]," he said on Tuesday.

Penn also confirmed previous reports that he had been working on a documentary about Khashoggi's death; however, the idea was actually spun out of another project he had recently attempted: a documentary about the Arab Spring, which, according to Penn, brought him face-to-face with Syrian President Bashar Assad.

"I had remembered all the pundits and even heads of states, most people in the State Department of our own country … everyone anticipated that Assad would fall within months of the beginning of the Arab Spring," Penn said, explaining that the documentary would examine, five years later, why Assad was still in power.

Joined by a friend from Beirut, Penn allegedly met the Syrian leader, "who was, for that part of the story, willing to let us," he said. "For me, the criteria would be that we'd be able to move without minders and talk to people, anyone we wanted to, and that he would make available those who had been journalists for what was an opposition news that had been five years dead," along with "imprisoned ISIS soldiers," Penn added.

He noted that Assad "agreed" and "understood" that Penn would "come in illegally later to Turkey" to interview members of the U.S. intelligence community and nongovernmental organizations.

However, the alleged agreement didn't last.

"Very quickly after that … one thing after another was being taken away from the freedoms that we would have to tell the story," Penn explained.

Then came Khashoggi's death.

"We wanted to do a story about that, and we had great contacts in Turkey," Penn said. "And we went, and it was when I met his widow [Khashoggi's fiancee, Hatice Cengiz], I thought, 'This is the whole story.'"

He described Cengiz as "an extraordinary woman," and "very much willing to honor her partner's memory," but Penn soon discovered that a "formidable documentarian" already had a similar project in the works.

"The other documentarian was already very financed and somebody I thought was great," Penn said. "And so my interest was in telling the story, and I thought, 'Well, we'll just let them do it.'"

His focus turned to Bob Honey Sings Jimmy Crack Corn, the sequel to his debut novel, Bob Honey Who Just Do Stuff. Both books follow Honey, a septic tank salesman turned assassin with an aversion to the elderly, technology and a U.S. president dubbed "Mr. Landlord."

Honey describes the fictional politician as a "violently immature 70-year-old boy-man with money and French vanilla cotton candy hair." As if this not-so-subtle description wasn't enough to draw comparisons with the actual 45th president, Penn made sure to sprinkle in lines like "Tweet me bitch, I dare you."

Both novels also make a number of thinly veiled references to real-life people and things, such as Rudy Giuliani and the U.S. government's response to Hurricane Katrina.

Penn told Theroux that he simply wanted to create "a moral code that made me giggle in the den off my kitchen when I wrote."

"I am not unaware of my reputation for self-seriousness," Penn said, "which is only true relative to social discomfort anyway. Everything's just sort of a mask because, you know, I'm the silliest guy in the room with everybody else I know. And finally, I had to write my silly-ass novel."

Penn's "need" to write surfaced when he was a child, but it wasn't until 2015 that the choice was no longer a conscious decision.

"One of the things that I think about a lot because I have a 26- and 28-year-old, science tells us that it's game over. Basically, you can get a Tesla, you can do whatever you want, but with climate change, we are going to be degenerative matter shortly," Penn said. "But we don't know how the molecules of the world are going to regenerate themselves. … I know that even if it's all over, I can try."

Penn later added, "It's like those kids in Parkland. Forget about everything else — and I've talked about this before — anybody that's ever heard a long-barreled automatic weapon in an open space knows how scary that crack is, how violent. But the idea that's in the concrete walls of a school and it's your schoolmates' intestines on the ground, and on the next day, some of those kids can face those cameras with such articulation and such composure and such truth and courage — there's no way to not have hope."

By writing both Bob Honey novels, Penn was able to channel a sense of hope through the titular character, all while being distracted from the noise of the 2016 presidential election and Trump's term that followed. But there was no financial pressure either — he didn't have a film budget to stick to.

"If I want to write about 20,000 soldiers and six of them are on unicycles standing on their head against a perfect sunset, it's not going to cost me a lot of money to write it in a novel," Penn said. "Nowadays, because there are too many non-film people running what we call the studios, they're losing people that fell in love with that girl called cinema. They're number crunchers … whatever, they might be wonderful people, I don't know. In my experiences, they're mostly not."

Penn doesn't intend to adapt either novel, but he's not opposed to someone else doing so.

"Part of what liberated me to feel great about writing this, and what will continue to liberate me about writing novels — because I'm going to keep doing it, despite the critics — is, if a filmmaker I trusted wanted to do this, and I could maintain my relatively humble lifestyle for a year or two just based on what they paid me to own it, then I don't want to have any part in the making of it," he said. "I won't make it, but I hope somebody does."

For now, Penn's wrapping up directing Flag Day, a project penned by Jez Butterworth based on Jennifer Vogel's 2005 memoir, Film-Flam Man: The True Story of My Father's Counterfeit Life. Both of his children, Hopper and Dylan Penn, will star in the film. Due to a last-minute cast change, Penn even got the opportunity to play their father.

With a successful film career, encounters with Mexican drug lords and a penchant for writing, one might think he'd consider penning an autobiography.

His response? "I will absolutely … not."