Jon Lovett doesn’t like birthday attention. Sitting in a SiriusXM studio, he concedes that birthdays are “a fun opportunity to get your friends together,” but having all those eyes on him makes him uncomfortable. It’s a bit odd to hear a man who hosts two podcasts — including one he just taped in this very studio — discuss his uneasy relationship to attention. It’s even odder given he has just returned from filming the upcoming season of Survivor.
Lovett properly entered the public eye in 2008, when, after trying stand-up in New York and then working as a speechwriter for Hillary Clinton when she was a New York senator, he was hired as a speechwriter for President Barack Obama. After spending a term in Washington, D.C., with the Obama administration, he went to Hollywood and co-created 1600 Penn — a short-lived network sitcom about a fictional First Family that prompted our critic to write, “What’s onscreen is so tepid and unimaginative that it practically compelled my mind to wander.” Still, Lovett stayed in L.A., and he and fellow former Obama staffers Tommy Vietor, Jon Favreau, and Dan Pfeiffer started a limited-run podcast for The Ringer covering the 2016 election called Keepin’ It 1600. After Trump was elected, they went out on their own with Pod Save America. It was immediately successful — post-Obama, it turned out, liberals were eager to listen to a bunch of his former staffers talk about how to get the country back on track (and shout a bit about bad Republican behavior). In the years since, PSA has grown to be just one part of the larger Crooked Media, headed up by Vietor, Favreau, and Lovett. They’ve launched more than 40 shows, including Lovett’s own, Lovett or Leave It. Most recently, they released a book, Democracy or Else: How to Save America in 10 Easy Steps. Lovett describes the character he plays in the Crooked-verse as “a heightened version of myself” — the cocky, impish little brother. In classic queer tradition, his jokes often tiptoe right up to the line of being in poor taste. (In an interview with Pete Buttigieg filmed during Pride, Lovett made a dick joke that Buttigieg pretended not to notice. Instead of letting this slide, Lovett said to the secretary of Transportation, “Frank Kameny did not protest in front of the White House so that you could ignore my jokes during Pride, Pete.”) Although he’s become a proper public figure over the years, he has managed to maintain an unusual level of control over his image. He rarely gives interviews, and since he owns his own podcast company, he has the final edit.
With an exception. For the better part of the past decade, Lovett was in a relationship with the journalist Ronan Farrow. They seemed to try to keep their relationship private for a while, but a certain type of person — PSA superfans, power gays — was very interested in this pair, especially after Farrow described proposing in his book Catch and Kill. (“I’d send him a draft and put in a question, right on this page: ‘Marriage?’ On the moon or even here on earth. He read the draft, and found the proposal here, and said, ‘Sure.’”)
Post-lockdown, the two broke up. It was around this time, incidentally, that Lovett began mainlining a bunch of seasons of Survivor. He hadn’t watched since college and found the whole premise soothing — democracy in action! Plus he was nearing 40, depressed, and taking edibles to put off working — if he were stoned, he reasoned, he officially couldn’t make any more “clerical, logistical, emotional, or personal” decisions for the day. Eventually, he tells me, fiddling with a paper cup, he “just started making little notes to myself about what I would say if I made a video application. And the more I started making little notes to myself, the more I got excited about the possibility of making the video.” Thanks to an NDA, the public didn’t find out that Lovett was going on Survivor until he was already in Fiji filming. (Neither did some of his confused friends, who didn’t understand why he wasn’t texting them back.) When the trailer came out in May, he was inarguably the best part. Between Survivor platitudes from his fellow players (“This will be the most important chapter of my life,” etc.), there’s Lovett saying, “I have no outdoor skills. What am I doing here? I went camping as a Cub Scout; I threw up and went home.”
From the trailer, it seems clear which classic Survivor archetype he’ll be edited into: the nerd. There’s a long tradition of lovable, strategic, fish-out-of-waters on the show that he seems positioned to follow in: John Cochran, Aubry Bracco, and Christian Hubicki. Still, you never know. He could be edited in the mode of Survivor’s most enduring gay archetype: the overconfident asshole à la Richard Hatch, the season-one winner, who, incidentally, Lovett remembers well. Hatch won the summer between Lovett’s senior year of high school and freshman year of college; Lovett was so excited he ran around his childhood house screaming. “At the time, I don’t think I would’ve voiced it out loud, but the fact that a bombastic, very smart, very cunning, nude gay man was about to win this thing, my closeted gay brain really latched on to it.” Whichever version of “Jon Lovett” emerges from the Survivor editing room will be discussed on Rob Has a Podcast’s multiple weekly episodes dissecting each episode of the show, be voted on in the Survivor Reddit’s “Player of the Week” polls, and become either a beloved icon or a supervillain to the show’s fans on X and TikTok (with them, there’s rarely an in-between). He says this was actually part of the appeal of the whole thing in the first place, why he decided to go on, during those dark pandemic days — the fact that he’d have to surrender his ability to control his story. “I got to have a fascinating, meaningful experience,” he says. “Going into that, I knew that once it was over, there’d be some time later, at which point it would be watched and picked apart. How old do you have to be before you just trust that if you just talk and show people who you are, that you’ll be comfortable with the result?” For him, the answer was 40.
In the meantime, he’s making some more uncomfortable decisions. Another impulse that struck him during the pandemic and he has since put into practice: wearing skirts onstage. He was nervous at first — “I was afraid to do it for reasons I couldn’t even express, because if I had said them out loud, I would realize I didn’t believe them: They’re all going to laugh at you kind of thing.” He did it, and it was fine, but talking to me about it, he couches the story by adding that “it’s not some defining or even remarkable or important act.” There’s a push-and-pull thing going on, one that he doesn’t seem to have figured out himself. “It’s interesting,” I tell him, before we stop talking, “that you describe yourself as an anxious, self-conscious person, and that you also went on one of the most popular TV shows in the country.” He agrees that it didn’t make much sense. I ask if it was impulsive. “How could it be impulsive? It took months.” I ask if it gave him anxiety. “No.” I ask if he was at peace with the choice. “It’s just a funny thing to do to go on Survivor. Honestly, it’s so funny. Even now, it’s just — so silly.” Maybe it’s all as simple as that.
