I have to admit I am very bad at keeping up with podcasts. I will start one that someone recommends to me, then quickly forget to download new episodes. But there’s one podcast that I listen to every week, without fail: Jon Lovett’s Lovett or Leave It, which began in March 2017. Lovett is funny, smart, dynamic, and creates a space for a wide range of diverse voices. He is, essentially, the perfect podcast host.
Before he entered the world of podcasts, he was a speechwriter. He volunteered for John Kerry’s presidential campaign in 2004. In 2005, Lovett was hired to work as an assistant for speechwriter Sarah Hurwitz and in 2008, he wrote speeches for Hillary Clinton for her presidential campaign. After she lost, Lovett won an anonymous contest to write speeches for the Obama White House; he worked as Obama’s speechwriter from 2009 to 2012.
Fast forward to 2016, and Lovett — alongside fellow Obama alums Jon Faverau, Dan Pfeiffer, and Tommy Vietor — co-hosted Keepin’ it 1600, a political podcast from The Ringer. They expected for it to only cover the election year. (They were wrong.) After Trump’s election, three of them (minus Pfieffer) launched Crooked Media, rebranding Keepin’ it 1600 to Pod Save America. The show is now one of the most popular podcasts in the U.S., and Crooked is now home to 15 podcasts, from Pod Save the People to Keep It to Hysteria, as well as a host of fundraising and get out the vote efforts (aptly called Vote Save America).
Lovett or Leave It is a weekly live show hosted by Lovett, featuring a rotating panel of guests. They discuss the week in news, and play games, like “Okay, Stop” (where Lovett plays a clip from the week and panelists shout “Okay, stop,” to discuss what’s happening). Every episode ends with a “Rant Wheel,” where the wheel lands on something the guests want to rant about. A recent guest on the show was Ronan Farrow, Lovett’s fiancé. (They got engaged in 2019 when Farrow, a Pulitzer Prize-winning journalist, asked Lovett to marry him in a draft of his book, Catch and Kill: Lies, Spies, and a Conspiracy to Protect Predators.)
In the midst of the Democratic primaries and prepping for a Crooked Media tour, Lovett took the time to answer some questions over e-mail.
Can you talk about your Jewish upbringing?
I grew up on Long Island. My family belonged to North Shore Synagogue. Hebrew school, High Holidays, big bar mitzvah, the whole shabang.
What was your bar mitzvah theme?
The theme was “Jon’s World” because I couldn’t decide. So it was just a bunch of cardboard cutouts of stuff I liked — which at that point was mostly video games and television shows.
Growing up, did you ever think your career would take you to where you are now?
Yes. It’s exactly what that witch told me would happen.
What is the most difficult part about your Crooked Media job?
One of the hardest parts of keeping up with the news and talking about politics these past few years is not getting exhausted by the daily grind of scandals and chaos and misdeeds. And I say that as someone who has it pretty easy and who really has nothing to complain about it. It’s important for everybody that we find ways to stay in the fight, stay optimistic, stay engaged — even if at times you want to throw your phone into a volcano.
Does your family understand what you do? Do they listen to your podcasts? (I am just picturing trying to explain to my grandma what a podcast is.)
A lot of my family listens! My father’s politics are… different than mine. But everyone in my family and all of my friends have been so, so supportive.
One of my favorite Lovett or Leave It episodes was from this past fall, when you were talking about Yom Kippur services with Moshe Kasher and Michaela Watkins. Do all the Jews in Hollywood know each other? Do you feel a part of a Jewish community in L.A.?
Increasingly as I get older I’ve been seeking out that kind of community. I saw Moshe and Michaela at temple which was a delight but to be honest, it was one of the first times I’ve gone to temple in a long while. So maybe all the other Jews in Hollywood know each other but not this Jew. At least… not yet.
How do you navigate sharing your Jewish identity online?
I don’t feel as though I “navigate” sharing my identity, so much as my identity is who I am — a Jewish person, a gay person, a person with other qualities, and if I am sharing my views or my experiences, these parts of my identity will naturally be part of how I express myself. It’s not like I’m starting a lot of tweets with, “As a gay Jew…” “As a gay Jew, I loved the film Parasite.” “As a gay Jew, I could go for some pizza.” You get it.
How do you feel like your gay and Jewish identities intersect with each other, if at all?
My Jewish identity wants carbs and my gay identity wants abs. JOKES ASIDE, what connects the two for me is the experience of being on the outside looking in — of being an observer figuring out how to fit in, how not to fit in. Honestly, that was more about being gay in my personal life, but part of being culturally Jewish to me is about embracing your place in a diaspora, in a big diffuse group of people always aware of the struggle to be accepted and the danger that has come for those who weren’t. There’s a lot in common there.
What does Jewish humor mean to you in 2020, particularly in the face of rising anti-Semitism?
Does it have to mean something different in 2020? I’m not sure that it does. Every once in a while I see Mel Brooks eating at a deli outside in Beverly Hills so I’ll just get up the courage to ask him until someone tells me to leave.
Who was your favorite Lovett or Leave It guest?
Wouldn’t dare to pick a favorite. We’ve had incredible guests — some of the smartest and funniest writers, performers, comedians, politicians, activists, candidates. Stacey Abrams joined for our show at Radio City Music Hall. Over the past year we’ve talked to many of the Democratic presidential contenders. I was about to name a few others but to name anyone is to not mention some of the best people around. So no dice!
Last question: What’s your ideal bagel order?
Buckle up, because it’s tuna salad on cinnamon raisin. And I don’t care who knows it.
Header image courtesy Crooked Media by Amelia Beamish. Lovett or Leave It records live; You can get tickets to upcoming shows in Los Angeles, Spokane, Seattle, Portland, and more, here.
