It’s just minutes before her prime time cable news show goes live at 7 p.m., and conservative commentator S.E. Cupp ’00 is in a Manhattan studio on a Thursday in October, camera-ready and cracking jokes. “It’s finally leather weather!” she laughs, adjusting her black leather skirt. But she’s immediately all business at a cue from a producer—jumping into a remote interview with Oklahoma Senator James Inhofe, who’s in Washington, D.C., about a surprise attack in Niger that killed four American soldiers. It’s been a hot topic on “S.E. Cupp Unfiltered”—which premiered in August on HLN, CNN’s sister network—with Cupp wondering why so much focus has been on President Trump’s remarks to one soldier’s widow, rather than on a lack of information from the Pentagon about the deadly ambush. Cupp wants answers—and she assumes Inhofe, a fellow Republican and senior member of the Armed Services Committee, wants some, too. Yet the interview doesn’t go as expected. When Cupp asks him for “the most pressing questions” about the attack, Inhofe responds, “Well, what questions are unanswered?” She pushes the senator further, asking if the attack was due to “an intelligence failure.” Inhofe again doesn’t answer directly, saying there’s risk anywhere troops are on the ground.
Cupp’s allotted time with Inhofe ends, and she sits back in her chair. There’s a long pause before she gets a signal that she’s no longer on camera—and then she explodes with amusement. “What the—?” she says in a singsong voice, ending the sentence with an expletive. “That was bizarre. I can’t wait to watch this interview back—it’s going to be painful!”
And with that, Cupp shakes off the exchange and smoothly moves on to the next segment; she’s a TV veteran, and it takes more than one awkward conversation to fluster her. The right-leaning host has spent years dealing with unpredictable politicians and outspoken pundits as a frequent contributor on CNN, MSNBC, and Fox News and programs like “Real Time with Bill Maher” and “The View” and as a writer for the New York Daily News, Glamour, and CNN.com. She has built a reputation as someone who isn’t afraid to speak her mind—and these days, she’s calling the shots with her own program. Cupp points out that during this particular week, she insisted on long pieces about the Niger situation. “Foreign policy usually makes people change the channel, and I know that,” she says. “But I feel like it’s my job, my responsibility, to share the stories that matter with as many people as possible—and this matters. That’s a gift.”
About two hours earlier, Cupp is in her office two floors below the studio, ending a meeting with producers. It’s been a full day already, beginning with a 10 a.m. conference call as she commuted from the suburban Connecticut home she shares with her husband and three-year-old son. At the moment, she’s in casual wear, with a camouflage scarf layered over a gray T-shirt and snakeskin print leggings, hair in a messy bun, and her trademark glasses in place (yes, they’re real). She notes that there’s one big way “Unfiltered” stands out in the contentious world of cable news: it’s a no-yelling zone. “The people I invite on the show I truly admire, respect, and want to hear more from,” says Cupp, whom New York magazine’s pop culture website vulture.com has called one of TV’s smartest pundits. “Whatever we’re talking about, we try to do it civilly and quietly. We are passionate and emotional about everything we talk about, but the audience can hear us articulate our points. No one is shouted off.” Cupp says she doesn’t automatically see someone with a different opinion as an enemy, and she tries to book guests each night that offer a range of views. It’s something she appreciated co-hosting CNN’s re-launch of “Crossfire” from 2013 to 2014, where she often found common ground with colleagues like Van Jones, a former special adviser in the Obama Administration. “A lot of people like to tune in to shows that reaffirm their beliefs and to see someone be as angry as they are; I get that,” she says. “But I’m over that, and I have to think that other people are over that, too.”
Still, Cupp is vocal when it comes to being a conservative, even if her thinking sometimes doesn’t align with so-called conservative values. She grew up Roman Catholic, but is now an atheist. She backs gay marriage and opposes the death penalty, yet she’s pro-life and supports gun rights. And while she’s a proud Republican, Cupp won’t uniformly toe the party line—calling out the GOP on the air, for instance, for not being as outraged by the Niger ambush as they were about the 2012 Benghazi attack. “I’m very open when I have some criticism for the party or the president. I’m also not totally defined by formal conservatism,” she says. “I talk about these issues from a place of common sense. I hope people find that to be accessible and refreshing.” Yet that means both the left and right have slammed her at times. When Esquire political blogger Charles Pierce disagreed with her comments on President Obama’s tax policy, he called her “a colossal idiot.” Several years ago, after Cupp criticized Planned Parenthood, former MSNBC and ESPN commentator Keith Olbermann ’79 tweeted that she was “a perfect demonstration of the necessity of the work Planned Parenthood does,” sparking controversy when some thought he was implying that she should have been aborted—or at least, that she should never have been born. And during the presidential election, Cupp’s open disapproval of Donald Trump kicked off a Twitter attack. “One of the dumber pundits on T.V. Hard to watch, zero talent!” he wrote, later adding that she was “a totally biased loser who doesn’t have a clue.”
Cupp shrugs off the criticism and points to a photo on her desk of Trump shaking her hand last year following the presidential debate in Miami. She’s known him for years; both have appeared on Fox News, and she’s friendly with his son Donald Jr. She even lived in one of his New York apartment buildings at one time. (He sent her a monogrammed cutting board as a housewarming gift.) So Cupp kept an open mind when the real estate mogul first announced his candidacy. However, she says it soon became clear that his views didn’t align with hers or those of some other Republicans. “I think he’s divisive and the opposite of a leader. But my personality issues with him aside, I don’t think he’s a real conservative. I don’t think he knows what conservatism is, and he doesn’t have a lot of undergirding principles,” she says. “I’ve said that I thought he wore the party like a rented tuxedo to get through the election. He doesn’t care about the party. This is not ‘a shining city on a hill.’ This is not Reagan. This is the basest worst of us. So we’re kind of keeping our head down, doing the hard work, and waiting for this to be over.”
But when it comes to her HLN show, Cupp knows that her viewers are interested in more than Trump—and she is, too. So she always finds room for compelling human-interest stories or odd news of the week; her panel on this day discusses the fact that shops in Hawaii are locking up Spam because people are stealing the popular canned meat to sell on the black market. She’s also interviewed several of TV’s “Real Housewives” and says her dream guest would be Andy Cohen, an executive producer of the “Housewives” franchise and host of Bravo’s late-night talk show “Watch What Happens Live.” “I’m not only about politics,” says Cupp, “and I don’t think most other people are either.”
Growing up in Andover, Massachusetts, a young S.E. (for Sarah Elizabeth) trained seriously with the Boston Ballet company and planned to dance professionally. But she burned out at seventeen—she has written in the past about her battle with eating disorders that began in ballet school—and changed direction. At Cornell, she thrived as an art history major and at the Daily Sun, where she was an arts and entertainment writer and editor. “She wrote wonderfully articulate, intelligent, sensitive reviews of exhibitions,” says Johnson Museum of Art director emeritus Frank Robinson, who asked her to join the museum’s advisory council after graduation. “She really understood the role of art, and the role of the museum as part of the educational mission of Cornell.” In fact, Cupp is such a fan of abstract painter Wassily Kandinsky, she has a tattoo of the artist’s signature on her lower leg. “It’s like he signed me,” she says, pulling up her leggings to show it off.
Cupp describes her time at Cornell as “a wake-up call,” and she can still remember the exact moment that prompted her to question her beliefs: at a debate on affirmative action during her freshman year, where she found herself agreeing with Jeremy Rabkin ’74, then a government professor and a prominent conservative voice on campus. “I walked in thinking I’m a liberal, because liberals are good people and conservatives are bad people—at least from what I saw in the movies,” she says. “I was so horrified that I was agreeing with Professor Rabkin’s points. He made them very logically. He wasn’t angry. He wasn’t racist. He just said, ‘This is not good and here’s why.’ That really got my attention and I thought I needed to learn more. I literally went on a fact-finding mission to figure out what I believed politically, and it led me very clearly down one road.” She questioned her faith, too, even though she says that the devout have always fascinated her—an interest that later motivated her to earn a master’s degree in religious studies from NYU. “I always say I don’t believe in God, but I aspire to be a believer one day,” says Cupp. “I’m really envious of deeply religious and spiritual people. I’ve spent a lot of time trying to get there mentally. I just never could.”
After leaving the Hill, Cupp worked at the New York Times, wrote for publications like the Washington Post, Slate, and Maxim, penned two books (Losing Our Religion: The Liberal Media’s Attack on Christianity and Why You’re Wrong About the Right: Behind the Myths—The Surprising Truth About Conservatives), and served as a consultant for HBO’s journalism drama “The Newsroom.” She first broke out on cable TV at Fox News, and joined MSNBC in 2012 to co-host “The Cycle,” an ensemble talk show on news and politics. Cupp then moved to CNN to co-host “Crossfire” and later launched “S.E. Cupp’s Outside With Insiders,” a series on CNN.com in which she interviewed influential politicians while hunting, shooting, or fishing. The show caught the attention of HLN’s chief executive, who helped develop “Unfiltered.” As someone who’s followed Cupp’s career for nearly two decades, Robinson says that he’s impressed by her smarts and how she approaches complicated issues. “I’m a Democrat and she’s obviously not, but I really respect her opinions,” he says. “They’re cogent, balanced opinions that actually make me rethink my own. I think if there were more people in the political conversation like her, we might be able to build a consensus in this country—which we don’t have right now—and move things forward.”
Cupp is also concerned that the U.S. isn’t moving forward, especially given the current political climate; while she’s a fan of vigorous debate, she thinks this country’s leaders need to tamp down on the vitriol if they’re going to work together to solve problems. And while she’s not shy about offering her opinions on how to do so, Cupp has no plans to run for office herself. “I’d be awful at it,” she says, before racing away, since she’s late to get her makeup done for broadcast. “I’d rather just be here, unfiltered,” she adds with a laugh, “and not have to keep my mouth shut.”
Editor’s note: Although Cupp’s show aired at 7 p.m. when CAM’s story was reported, it now airs at 5 p.m.
Consider supporting your alumni magazine!