This is a fraught time to be a political comedian in America. It’s something Stephen Colbert learned when CBS suddenly canceled The Late Show. And it’s something comedian Jena Friedman experienced in an even more visceral way the last time she crossed the border back home to the U.S.
In her fourth appearance on The Last Laugh podcast, Friedman weighs in on the end of the late-night show that served as her very first TV writing gig and tells the harrowing story of being grilled about her jokes by U.S. Customs and Border Security. She also talks about putting together her new TED talk on comedy and AI, recalls the time she nicknamed her fetus “Jeffrey Epstein” on Colbert’s show, and previews her new stand-up hour ‘Motherf---er’ about becoming a mom and losing her own mom at the same time.
In addition to getting her start writing for The Late Show With David Letterman, Friedman has been a regular presence on Colbert’s show over the past decade, beginning with his live Election Night special in 2016 that quickly went off the rails when it became clear that Trump was going to win. That night, Friedman made a prophetic plea to women watching to “get your abortions now.”
“Like a lot of things right now, there’s no definitive truth, we don’t know exactly why the show was canceled,” Friedman says of CBS’ decision to kill The Late Show. “Was it for ratings? Was it because of political reasons? I think the larger issue, for me, is that I personally look to comedians I admire—particularly outspoken political comedians—in times of uncertainty. And just the fact that Colbert’s show was canceled and canceled so swiftly in such a scary moment really made me sad.”
As “scared” as she was during that first appearance on his show in 2016, Friedman says she took “comfort in knowing that things are going to be OK for us as long as people like Stephen Colbert are on the air, able to say what they’re saying.” She adds, “That at least is one sign of a democracy that is not totally in palliative care. So this news is just another notch on—I’m not sure what the right analogy is—the tool belt towards fascism.”
The freedom she felt as a comedian appearing on Colbert’s show was on full display when she sat down with him to promote her book of essays called Not Funny in 2023. During that appearance, she revealed to the world the disturbing pet name she’d given her baby before it was born.
“Because my husband’s last name is Epstein, naturally we named the fetus Jeffrey,” she joked at the time, adding that because she was an older mom with a high-risk pregnancy, if “god forbid, anything went wrong we wanted to be able to say, ‘Well, maybe Jeffrey Epstein killed himself.’”
“Whenever I’m on Stephen’s show, because he’s such a good sport, I always want to give him something that he’ll definitely cut,” Friedman tells me. “And I really thought he was going to cut that. Because when I came out and he was like, ‘Here’s a picture of Jena with her baby and her husband.’ And I was like, ‘Stop trying to humanize me to people!’ So to his credit, he kept it in, and I thought that was really cool.”
While Friedman, who also spent years working for The Daily Show under Jon Stewart as a field producer, understands the “economics of late-night” are not exactly on solid ground, she is very skeptical that the decision to ax Colbert was made for “purely financial reasons,” as CBS claimed. “Given the timing, it sure looked like they were trying to appease Trump,” she says.
She also sees the move in the larger context of the Trump administration’s efforts to silence comedians who dare to criticize the president. And she witnessed just how chilling those efforts can be when she crossed back into the U.S. from Canada earlier this year after she performed as part of a TED conference in Vancouver.
Friedman was going through security before getting on her plane back home to L.A. when a man who she only later realized worked for U.S. Customs and Border Protection asked her what she was doing in Canada. When she told him she was performing comedy, he asked what she jokes about. “For some dumb reason, I decided to flirt with him and I was like, ‘I joke about everything other than airport security,’” she explains.
Then came the question that really unnerved her: “Do you make fun of politicians?”
Friedman, who most certainly makes fun of politicians, reflexively said “no” and he ushered her through. “The guy wasn’t trying to troll me or tease me, he literally was just following orders,” she says now. “It was such a benign but insidious question. It felt shocking. Now it doesn’t feel shocking at all because of everything else that’s going on.”
She decided to post about it on social media at the time, mostly as a warning to other comedians, who might not be blonde, white, American citizens, that they should be prepared to answer similar questions and perhaps face more dire consequences than she did. “I look like Ann Romney,” Friedman jokes, saying the first thing she did was text a comedian friend of hers who was also coming back in the States that day and happens to not be white. “I just texted her: ‘Do not tell them that you’re a comedian.’”
But instead of being intimidated into silence, Friedman says she plans to keep speaking out against the administration—including in a piece she wrote for The New Yorker about her border experience and, presumably, in the new hour she is working out at the Edinburgh Fringe Festival next month.
“I just feel like we have to make noise, just be as out there as you can right now because we still have that privilege,” Friedman says. “And then, you know, hopefully I won’t have trouble getting back into the country at the end of August, but I don’t know.”
Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.
