As someone who first made his name in political circles as a speechwriter, Jon Lovett’s route to Washington started in a less conventional way: a math major.
“I wrote op-eds in the college newspaper, I drew political cartoons, I tried to write funny things that kind of touched on politics,” said Lovett, who along with other Obama administration alums started Crooked Media in 2017. Lovett is bringing his live, weekly podcast Lovett or Leave It to St. Paul’s Fitzgerald Theater on July 14.
“I said this to a friend of mine that I actually went to college with a couple of years later, which is, ‘I think I’m funny enough to be a funny professional. But I’m not sure I’m funny enough to be professionally funny,’ he said.
However, he’s managed to make a pretty good career of it. He first got on the radar of a Hillary Clinton staffer as they were writing a speech for the then-senator to give at a roast for Barbara Walters.
“They’d heard through the grapevine that I’d done open mics. I don’t know how this had come to them; people thought I was funny. That was very nice,” he said. “I was I was 22 I just come to DC I was starstruck by even the idea.”
It was in those phone calls that he had one of his proudest comedic moments: He made Al Franken laugh.
“I had a joke about Rick Lazio working in a deli. That’s what got him,” he said. “It still makes me happy thinking about it, that I could make someone I really respected so much in terms of comedy laugh.”
Intertwining Judaism with politics
Lovett went on to become a speechwriter for Clinton, and then got hired by the Obama team after the 2008 Democratic primaries. He grew up in New York and said he has always felt very culturally Jewish.
“There’s what it means to be Jewish in terms of going to temple, tickets for Rosh Hashanah. Learning your Torah portion, doing your bar mitzvah having the party not going as much after; this is the story,” he said. Now in Lost Angeles, he said he is considering joining a temple. “I feel really connected. It’s a kind of immigrant experience. It’s the diaspora. Every once in a while, I’ll go out to lunch with a friend of mine out here. And he’s Jewish. And we’ll go to like Canter’s Deli, or Nate’n Al’s. And we’ll just have lunch. And I’ll just think like, this is what my grandfather did. This is what two Jews do, and I will become an old Jew. And when I’m an old Jew, I will be at this deli with this person and will be two old Jews who’ve been coming to this deli for 50 years to have this conversation. And I love that.”
Lovett said that so many of the horrors that Jews have gone through in our shared history,
“In the back of our minds, that you can lose everything, that you can be taken advantage of, that you can find yourself in a place that looks very different very quickly, I think is a part of what it means to be Jewish in a very big way,” he said. “And I think it actually fundamentally informs our politics, our culture, our way of seeing the world, our compassion, our liberalism and progressivism. I think it is the thing that undergirds and connects Jews around the world, but especially in America, because of the history that brought us here.”
Back on the road
Lovett’s show started at the Hollywood Improv in Los Angeles, and the shows were recorded for the podcast which is released every Saturday. The show is a mix of standup, and interviews with guests who range from comics to politicians. But like all other things, COVID shut the door on live shows. The show went through themes: “Back in the Closet,” (Lovett is gay and engaged to author/journalist Ronan Farrow), “Homestretch” (the leadup to the 2020 election), “Back in the Closet-Elect” (post-election), “Vax to the Future” (vaccines, obviously), and now, “Live or Else.”
The show started touring again in March.
“It rules,” he said. “I feel very happy that we get to be, for a lot of people, one of their first – if not their first – big live events back with people. It’s hard to imagine how much you’ll miss something until you’re back in it. And it has been really fun to be back in front of crowds and to see people remember how much they love being around people.”
Lovett said his show essentially started as a pub quiz in 2017. By September 2019, he’s in front of 5,000 people on stage at Radio City Music Hall.
“Within a few months, it’s all gone,” he said. “And now that we’re coming back, after every show I want to go out and celebrate, I want to say hi to everybody in the crowd, because I just I don’t want to take it for granted. And I feel the audience having the same experience of just getting to do what we used to do. But understanding that it has a kind of new meaning. And that’s really nice. That’s a really exciting thing.”
Tickets are still available for purchase online.