Jon Lovett on Bringing Late-Night Flavor to Political Podcasts

The host of ‘Lovett or Leave It’ and ‘Pod Save America’ talks using comedy to make progressives feel less ‘hopeless.’

Photo Illustration by Elizabeth Brockway/The Daily Beast

Jon Lovett is sitting in a booth at his favorite New York diner, wearing a t-shirt and navy blue “Friend of the Pod” baseball cap. Though he’s lived in Los Angeles for the past several years, he says he likes to get back to his home state as often as possible. But this might be the first time he’s doing so as a legitimate celebrity — at least to a certain segment of progressive nerds — as he hosts two sold-out tapings of his popular podcast Lovett or Leave It at the Beacon Theater as part of the New York Comedy Festival.

It’s been about 10 months since Lovett, along with former Obama administration colleagues Jon Favreau and Tommy Vietor, decided to end their Keepin’ It 1600 podcast and start Crooked Media, home to Pod Save America and a slew of other political offerings including Lovett’s comedy-driven show.

“When we decided to do this, we didn’t have a plan. We just had this feeling like we wanted to launch a company that answered some of our frustrations and spoke to why we were worried, why we were angry, like a lot of other people,” Lovett says. They feared that the Keepin’ It 1600 audience wouldn’t follow them to their new platform. “And then it just started growing, it just started working.”

After some deliberation, the former speechwriter orders the breakfast club sandwich, essentially a grilled cheese with two fried eggs and bacon in it. “What I really want is grilled cheese, two eggs and bacon, and you can kind of convince them to deconstruct it,” he says from experience. He adds tomato juice because it has less sugar than all the other options. “Juice is a waste,” he says. “This could be french fries, this could be bread, this could be a cookie. I mean, orange juice? This is ridiculous.”  

If those lines make him sound like a stand-up comedian, it’s because he is one, in a sense. Lovett spearheaded the joke-writing sessions for some of Obama’s best White House Correspondents’ Dinner speeches — including the one in which he ribbed Donald Trump so hard that he may have pushed him into running for president. [Read Lovett’s rant on Trump skipping the White House Correspondents’ Dinner*]

Now, he’s taken those skills and translated them to Lovett or Leave It, which is performed in front of a live audience in Los Angeles or elsewhere around the country every week. Though it’s not on television — yet — the show looks a lot like the type of hyper-political late-night shows that have thrived under Trump’s presidency.

On Thursday night’s show in New York, Lovett and his panel — CBS News’ Alex Wagner, MSNBC’s Katy Tur and The Daily Show’s Michelle Wolf — took a humorous look back at the year since Donald Trump was elected. Before that, he sat down with Ronan Farrow, or as Lovett joked, “my longtime golf buddy,” to talk about his explosive reporting on Harvey Weinstein, as well as his frustrations with iOS 11.

Two nights later, the show began with a cold open taped sketch that would not have been out of place on Stephen Colbert’s Late Show. In a series of clips shot around New York City, Lovett can be seen leaving voicemails for White House Press Secretary Sarah Huckabee Sanders, begging her to help him book President Trump.

“Maybe you’re not calling me back because you have some concerns about some of the things I’ve said,” Lovett says into the phone at one point. “Dotty old racist, Fascist Hamburglar, evil baby boomer supernova, the worst person we’ve produced in half a century.” He promises her that if he had Trump on his show, he’d be “tough, but fair.”

A sheepish smile forms across Lovett’s face when I suggest that Lovett or Leave It is in any way similar to the late-night shows. “I mean, it’s a podcast,” he says.   

Lovett gets even more uncomfortable when I ask if he’d ever consider bringing the show to TV were someone to give him the opportunity.

“You know, I’m famously humble,” he jokes before taking a long pause to decide how he wants to respond. “Look, we love doing the shows as podcasts,” he says eventually. “We’ve had success pretty quickly. We launched the company because we were angry and frustrated and wanted to be involved. And it’s been incredibly gratifying to see how people have responded to it.”

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“How that evolves, I’m not really sure,” he continues. “It could involve TV, of course, that would be really cool. Some kind of a streaming show? That’d be great. But I don’t know. I don’t want to get ahead of where we’re at.”

We’re talking the morning after the sexual misconduct allegations against both Alabama GOP Senate candidate Roy Moore and comedian Louis C.K. broke. And just as late-night hosts have struggled to joke about topics that are not, on their face, particularly funny, Lovett marvels at the types of issues he has managed to tackle in what is ostensibly a comedy podcast. [Read Lovett’s rant on the Roy Moore allegations**]

Looking to hosts like Stephen Colbert, Seth Meyers and more recently, Jimmy Kimmel, Lovett says, “I think it’s great to talk about serious issues in an unexpected place with unexpected people.” As he’s joked on the show before, “It’s Friday night at The Improv and we’re talking about harassment.” During a live Pod Save America show in Washington, D.C., the audience cheered wildly for federal indictments of Trump campaign staff. “This is a concert venue and the biggest applause of the night was about an injunction,” he remarks.

“It’s a really hard subject and it’s hard to joke about,” he says of the escalating harassment and assault stories that seem to break every day. While on the one hand there was “pressure” for comedians to make jokes about Weinstein, Lovett notes that James Corden got in trouble for making the wrong jokes about it. But he also thinks it’s “absurd” that late-night comedians are “ignoring” the stories about liberal abusers for political reasons, as has been suggested by some on the right.

Lovett names former late-night host Larry Wilmore and current host Sarah Silverman as recent examples of some of his favorite guests. He describes them as having “that perfect balance between comedy and politics,” able to talk about the week’s news in a “substantive way” without sacrificing the essential element of humor.

The original idea for Lovett or Leave It was born when Lovett’s friend Lee Eisenberg, a writer for the American version of The Office and currently executive producer on Showtime’s SMILF, suggested that he host a pop quiz podcast about the week’s news with trivia and games. “In hindsight, it’s crazy that we didn’t do a test, we just did the first episode at the small room at The Improv in L.A. for like 60 people.”

They learned as they went along how to produce what ended up taking the form of a show like HBO’s Real Time with Bill Maher, albeit without the token Trump supporters like Jeffrey Lord or, god forbid, Kellyanne Conway. “We have a hard ban on devious morons,” he told me in January when I asked if he would ever welcome her onto one of his shows.

“We want to debate issues and there are big debates to be had on the left among Democrats and among liberals,” he says. “And our door is always open to intellectually honest conservatives.” He cites Tim Miller, an adamant #NeverTrumper who worked on the presidential campaigns of both Mitt Romney and Jeb Bush as someone he’s fought with on Twitter “a million times,” but has “carried himself with such integrity” over the past year.

“But we’re just never going to be a place where we need to have a pro-Trump person here to be balanced, that’s just nonsense,” he adds, emphatically.

As a group of three young white guys, the Crooked Media crew has faced some criticism for being too inside their own privileged, liberal bubble, including from a fan who stood up at the end of a recent taping in Richmond, Virginia and asked the hosts how they planned to “escape” that bubble and reach people who don’t agree with them.

Lovett points to the answer given by former Bernie Sanders spokesperson Symone Sanders, who is part of the company’s new contributor lineup and was on stage at the time. She essentially said it’s not Crooked Media’s job to reach those people.

“Sometimes we need to do a little self-care for what we’ve got going on right here,” Sanders said. She described Crooked Media’s podcasts as the left’s answer to conservative talk radio. “We need this. The bubble kind of needs to wake up a little bit,” she added, before praising the three founders for bringing more diverse voices like hers to the table.

“Symone Sanders is the fucking best,” Lovett says in response. “I feel so lucky that she’s signed up with us.”

In recent weeks, the crew has taken their show on the road, interviewing local Democratic candidates like Randy “Iron Stache” Bryce, who will challenge House Speaker Paul Ryan in 2018, and Virginia’s newly elected governor Ralph Northam. In the podcast recordings from those events, deafening applause greets these previously little-known figures, as if they were the most famous celebrities in the world.

“We have this platform that we’ve found ourselves in,” Lovett says. “We did not expect that would mean we’d get to go to Richmond and a thousand people would show up to see us talk about the news. If, through that, we can get people to be engaged, get people to pay attention, to volunteer, to knock on doors, make phone calls and vote — and get excited about these candidates — that’s a cool part of what we’re doing here.”

When Lovett, Favreau and Vietor launched Crooked Media back in January, they wrote a mission statement that said they want to “inform, entertain and inspire action.” They were pretty sure they could handle the first two, but the third depended on the audience. “It sounded good,” Lovett says of the mission. “Inspiring action and getting people to do something would be the easiest thing to stop worrying about. But we care about it and it’s why we started this.”

After Lovett, who grew up on Long Island, graduated from Williams College in 2004, he moved back to New York and started working as a temp paralegal. “At night I would either go do open mics or fill out law school applications,” he says. “Or watch TV, more than the other two.” He volunteered on John Kerry’s 2004 presidential campaign before moving to Washington, D.C., where he was hired as a speechwriting assistant for then-Senator Hillary Clinton in 2005. He stayed on as a speechwriter for Clinton during her 2008 race before landing in the White House working for Obama after he took office.

Then there was his short-lived stint as a Hollywood screenwriter after leaving the White House just as Obama was about to start his second term. “Making 1600 Penn was really fun, and I learned a lot,” he says of the political sitcom he created for NBC, which was canceled after one poorly-rated season. He sold two other shows that never made it to air and spent some time writing on the final season of Aaron Sorkin’s The Newsroom.

As recently as last year he was “slowly trying to write this drama about an election that falls apart” for Showtime. “I was so excited about it, but I really struggled to write it,” he says. “It got harder and harder as Trump became more of a thing. Because it just felt like Trump was the drama. We were watching something fictional unfold.” When I ask whether he thinks Trump has driven fatigue for political drama in terms of TV viewership, Lovett says, “If they didn’t watch it, that would be a great problem to have. I couldn’t finish writing it.”

Trump’s rise also made Lovett want to reenter the political world. “I didn’t want to go back to D.C. but I wanted to be involved in some way,” he says. “I think if Hillary had won, I would have been like, OK, I’m going to write a comedy now.” Instead, he got together with his Keepin’ It 1600 co-hosts and decided they needed to do something big.

“In the midst of all this horror that’s happening in politics, it’s been this really rewarding, surprising thing,” he says of the new company’s success. “We really did decide in the days after the election, let’s do this. And now we’re doing this tour and people are wearing the shirts. And hopefully it’s not just getting people to listen and getting people through this, but it’s giving people something to do and a sense that it’s not hopeless.”

This month’s elections in Virginia, New Jersey and elsewhere were a sign that it’s working. “You saw this huge support from people for something different that swamped the Trump appeal to racial animus,” he says. “You saw a sign that we can do this. It’s not hopeless.”

With that Lovett, a man known for his incisive rants, delivers one of the best analogies for the 2016 election that this writer has ever heard.

“Throughout the campaign, it felt like Trump was the coyote,” Lovett begins. “And he was running across the ravine and he was over nothing. He was defying gravity. And the election was supposed to be the moment he looked down. And he was supposed to lose. We all thought, all this stuff that he’s getting away with on the campaign, these awful tactics, the election was going to show us that there was still gravity.”

“And then he fucking made to the other side and he ate the roadrunner!” Lovett continues, leaning forward across the table as he grows more and more animated. “And he took the roadrunner’s carcass to the White House and said, ‘Look. Look what I did. I killed the fucking roadrunner.’ Well, now what? The roadrunner’s dead and the coyote’s in the White House.”

“This felt a little bit like gravity,” he says of the first major Democratic victories in over a year. “The single most important thing any of us can do to hold Trump accountable is win the House. Virginia showed us that it’s possible, but not inevitable.”

While he’s not about to predict how Trump’s presidency will end, Lovett does think a lot about “the moment when Trump is gone.”

“And then there’s just all these people. They’re paying attention and active and have a habit of being engaged,” he says. “And now they’re just standing there and the biggest obstacle they’ve ever faced is gone. That’s an amazing opportunity. This is a group of people that will have the chance to shape the future of the country. That makes me really hopeful.”

If he can make them laugh on the way there, that’s not too bad either.