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.