Dave Rubin is one of the rising media stars of one of the craziest years in American political history. In a time when the political conversation is especially polarized and personality-obsessed, and when Americans of all ideological stripes are puzzled as to where the last year of Trump or Sanders-driven political lunacy leaves them, the comedian and talk-show host—a 39-year-old pro-choice, pro-pot, recently gay-married atheist with a strong allergy to organized religion—may come closer than political partisans of either party to reflecting the national mood of befuddlement: Is this moment horrifyingly real, or a sick joke, or an as-yet undefinable mixture of both? As host of The Rubin Report, a long-form online interview show with over 216,000 YouTube subscribers and 67 million total views, Rubin keeps up a front of cool equanimity, no matter how fraught or absurd the conversations get.“I’ve come around to believing that actually having Trump in the White House would be wonderful,” the alt-right provocateur Milo Yiannopoulos gushed on a recent appearance on Rubin’s show. Rubin is not a Trump supporter—but millions of Americans do want the real-estate mogul to be president, and Rubin didn’t butt in. “Trump is a direct creation of the progressive left. He has been brought about, he exists, because of the people we both hate.”“I’m with you there,” Rubin replied, smiling and lightly swiveling his chair. Then the conversation lurched in a less savory direction. This sometimes happens on The Rubin Report, given some of the riskier guests Rubin has hosted since his show launched in August of 2015—people like English Defense League founder and anti-immigration activist Tommy Robinson, or pro-Trump author and Twitter pugilist Mike Cernovich.“Most of the generation Trump, the alt-right people, the people who are like me, they’re not anti-Semites,” Yiannopoulos claimed. “They don’t care about Jews. They might have some assumptions about Jews, they might have some prejudices about Jews. Like the Jews run everything—well we do. That the Jews run all the banks—well, we do. That the Jews run the media—well, we do!” Yiannopoulos jerked his body forward and flapped his arms with increasing vehemence at each successive repetition, his voice a discomforting mix of jocularity and absolute seriousness, and his eyes jutting into an obsessive upward gaze. “I mean they’re right about all that stuff,” he continued, closing in on his point. “Now what you do with that is the issue. The reason they go on about it—”“I don’t even know where to start with that,” Rubin replied, looking bewildered and amused. On his show, Rubin is an easygoing onscreen presence who is seemingly incapable of exhibiting anger or rudeness, even when confronted with Milo Yiannopoulos levels of provocation. He surrounds himself with lightning rods without really being one himself—a hard balancing act even within a saner political discourse than the current one. He almost never tries to convince his guests that they’re wrong.“My policy with interviewing is I’m not there to teach the people I’m across from a lesson,” he told me during a recent interview. “Give people a long enough leash and if they’re going to hang themselves, they will.”***Like many throughout the country, Rubin has had his own ideological certainties scrambled. Today The Rubin Report is independently produced and counts former CNN host Larry King as an executive producer. As recently as March of 2015, Rubin was a host on The Young Turks, former MSNBC pundit Cenk Uyger’s left-wing online media empire.Rubin’s chief target these days is what he calls the “regressive left:” the self-described progressives whose alleged opposition to free speech and open inquiry, particularly around discussions of Islam, is to Rubin a betrayal of the principles they claim to stand for. “I believe the regressive left—the group of people who use illiberal tactics to silence those defending liberal principles—to be the left’s version of the Tea Party,” Rubin said during the opening of his March 18 episode. “If we don’t rein them in now then the left in America will be as fractured as the right.”The Rubin Report’s guests also include people like the English polymath Stephen Fry, who fretted to Rubin that “the advances of the Enlightenment are being systematically and deliberately pushed back,” and CNN anchor Don Lemon. But the show mainly reflects the schizophrenia of the moment and the rawness of Rubin’s own break with progressivism. He’s had on the aforementioned Tommy Robinson—as well as the British anti-extremism activist Maajid Nawaz, who coined the phrase “regressive left” to describe liberal apologists for autocracy or Islamic fundamentalism. Most noticeably, Rubin has hosted a string of liberal-minded guests stung by what they perceive as a growing intolerance within progressivism. He’s interviewed atheist thinkers from Muslim backgrounds, including Ayaan Hirsi Ali, who is openly reviled on the left. He launched his show with an interview with Sam Harris, a neuroscientist and religion skeptic who’s been the target of repeated accusations of Islamophobia among progressive-leaning critics.As Harris explains, Rubin’s show has become one of the leading venues for discussing what he sees as the left’s betrayal of true liberalism. “He’s just drilled down on this specific issue of what we now call the regressive left and the failure of so-called liberals to really stand for liberal values across the board,” says Harris. “What’s unique about Dave is that you can tell that he’s actually having a conversation where his opinions are in play,” he adds. “His mind can be changed on the topic he’s talking about, and these are edgy topics, and people are not necessarily comfortable about having their minds changed in real time about anything.”Gad Saad, an evolutionary psychologist and repeat Rubin Report guest, echoed Harris. “Dave contributes to battling many of these entrenched ‘progressive’ talking points,” he said, adding that Rubin “offers a very big platform to try to dispel some of those idiocies,” such as efforts to bring safe spaces and trigger warnings to college campuses.Positions like these might seem to put Rubin in the same camp as some of the right-wing provocateurs that he sometimes interviews—except they don’t. At one point, Rubin’s The Six-Pack, which ran from 2009 to 2012 and became a live show on Sirius XM radio during the last year of its run, was the top LGBT-interest podcast in the iTunes store. He grew up in a fairly secular Jewish household on Long Island, spent his entire career in either New York or LA, and got his job at The Young Turks through Kelly Carlin—daughter of George Carlin, one of the all-time icons of comedic transgression—who assures me Rubin is a stone cold liberal. “He questions things a little differently than other progressives, but he is still a progressive,” said Carlin. “Absolutely, he’s on the left.”In Rubin’s view, today’s progressives have drifted away from liberalism as he defines it. “There is a huge difference right now between progressives and liberals,” Rubin said. “That’s what people need to understand.” His political awareness was sparked as the result of a controversy that most Americans might barely remember, but which he witnessed up close. On Oct. 6, 2014, Sam Harris appeared on Real Time With Bill Maher, on a panel that included the actor and director Ben Affleck. Harris and Maher presented themselves as equal-opportunity critics of organized religion, but in a tense exchange Affleck accused them of holding bigoted views about Muslims. Harris tried arguing that there was a link between Muslim religious doctrine and jihadist violence, even if the connection stemmed from a theological fundamentalism that the vast majority of the world’s Muslims reject. Affleck reduced his contention to an easily-repeated sound bite: “Your argument is, you know, black people, they shoot each other!” Affleck shouted.Rubin, who was then at The Young Turks, watched the controversy over Harris’ appearance with a certain unease, as left-wing commentators, including Cenk Uygur, Rubin’s boss at The Young Turks, began to side against Harris and Maher. The terms of the debate were exasperating for Rubin: “Suddenly Bill Maher, who has stood for every liberal principle ever, who is further left than I am in certain respects—suddenly the onus is on him to prove that he’s not a racist.”To Rubin, slandering Maher and Harris’ criticisms of religious doctrine as anti-Muslim bigotry was the opposite of liberalism, and the refusal to even consider Harris’ arguments about the link between action and ideology revealed a startling complacency toward the real-world impact of Islamic extremism. “You can’t say you’re for gay rights but then be OK when certain people throw gays off roofs in the name of religion,” Rubin said. “All religions are a set of ideas. And you have to be able to criticize those sets of ideas.”Rubin’s employer entered the controversy in a way that would lead to what Rubin describes as an “awakening” for him. In an Oct. 9 segment titled “Bigotry 101,” Uygur alleged that Harris believed a majority of Muslims were in favor of ISIS-style beheadings. On an Oct. 10 segment on The Young Turks, author CJ Werleman declared that Harris was not just wrong about Islam but actually dangerous, especially since he allegedly advocated “a nuclear first-strike on the Arab world.” Uygur quickly became one of Harris’ loudest public critics and invited Harris to appear on The Young Turks during an Oct. 13th segment. On Oct. 23, the opponents sat down for a three-hour face-off on The Young Turks, where Harris calmly attempted to refute Uygur’s characterization of his work as unhinged or bigoted. Uygur countered that Harris was being disingenuous in how he was framing his own arguments. There’s little subsequent evidence that the lengthy sit-down with Harris had much of an impact on Uygur’s views of the author: During a November 2015 episode, Uygur accused Harris of supporting torture and nuclear strikes on Muslim countries, and linked his views to those of Donald Trump and Ted Cruz.At The Young Turks, Rubin had an uneasily close-up view of Uygur’s intellectual intransigence. “The way he became the leader of the group just relentlessly lying about Sam, and then to sit there for three hours with the guy and just double down on every lie—it showed just such a flaw in character,” said Rubin (through a media representative for The Young Turks; Uygur declined to speak with me for this article). In Rubin’s mind, Uygur’s inability to take a sober critic of religion like Harris seriously, and his boss’s unfounded and seemingly unshakeable assumptions about Harris’ alleged bigotry, exposed deeper problems within progressivism—a rising tendency within the left-wing camp that seemed more concerned with tarring its opponents as right-wing freaks than with defending liberal values like secularism and open inquiry.Rubin’s atheism led to his split from progressivism. So did his Jewish identity. “I don’t do anything in my life as far as I know, or at least consciously, that’s based in religion,” said Rubin, who says that fasting on Yom Kippur “and having some bagels that night” is about the sum total of his Jewish practice these days. But Rubin, who studied at Ben Gurion University for a semester in college, describes himself as “absolutely Jewish,” even if his Judaism is one of cultural and ethnic identification. Before the Harris controversy, Rubin had also been troubled by The Young Turks’ coverage of the escalation between Hamas and Israel in the summer of 2014, which he believed had whitewashed crucial details about the Palestinian Islamist group’s conduct during the conflict, something he says he had privately discussed with Uygur at the time. “The whole thing started becoming a house of cards,” said Rubin. “The whole progressive ideology just started crumbling.”Rubin left The Young Turks in March of 2015. Harris was the guest on the first full-length episode of The Rubin Report in September of 2015, an appearance that led to an acrimonious Twitter dispute between Rubin and Uygur. The public spat with his former boss has “cost me plenty of friends on the left. They’re authoritarians,” Rubin says of the “regressive left.” “They absolutely want to silence dissent.”***Standup comedy, where Rubin got his start, is among the most individual of the performing arts: There is no supporting cast or narrative frame, and it’s up to the comic to create a personality and a sense of humor in front of a room of strangers, and within a perilously thin margin of error. A standup comic is risking some fundamental part of their entire being every time they get onstage, and Rubin says the exhilaration of nailing a standup set is incomparable to any other thrill in life. “I remember one time I was at Gotham Comedy Club in Manhattan and I was just crushing,” Rubin recalled. “I remember it felt like I was standing behind myself, like I literally could see the back of myself with the audience there and I didn’t even feel like I was speaking. I’ve done most good drugs and I’ve never had that experience on any of them.”Rubin began his standup career organizing “bringer” shows in the Times Square area: In the late 1990s, comics would be given stage time if they could attract their own audience, something they typically accomplished through selling tickets on the street. Rubin and his group of comics, which he says included Melissa Rauch of The Big Bang Theory, packed restaurant backrooms throughout midtown, including the 200-capacity basement of the Times Square T.G.I. Friday’s, which Rubin notes was the largest T.G.I. Friday’s on earth at the time.Standup comedy was an ideal preparation for work as a political talk show host during a bizarre stretch for American politics. As Rubin explains, a comedian’s job is to describe reality as unflinchingly as possible. “Real comedians hold themselves to an extremely high standard of truth,” he explains. “The whole point of real comedy is that you can say something that is true and by being funny you can make it tolerable for people, and hopefully they’ll laugh at you too.”Rubin observed a shift in how standups treated their craft once the New York comedy clubs turned into a pipeline to Comedy Central and late-night television. Comedians “started treating the clubs as auditions for television” and became narrowly concerned with nailing a perfect 5-minute routine with little variation night to night. A similar tendency has gripped American politics, he says—a numbing preoccupation with pure image, and an aversion to spontaneity and risk. It’s a tendency that Donald Trump has exploited and exposed. “He’s present,” Rubin says of Trump. “By being present and being in the room you seem real. He doesn’t seem scripted. Trump for all his flaws comes off as a human.”Rubin says he hasn’t decided on who he’ll support in November. He’s leaning toward libertarian candidate Gary Johnson, but isn’t ready to commit to anyone yet. “I’m really not decided because it feels like the whole world is upside down and anything could happen between now and November,” he wrote by email in mid-June. “I’m hoping for an alien invasion at this point.”In Rubin’s view, Trump emerged out of the same kind of ideological drift that sparked his own career as a political talk show host. “The left won’t honestly deal with these issues,” says Rubin of the topics where Trump has been at his most Trumpian, like immigration and national security. “And for every time they’re afraid to say ‘radical jihadist terror’ or something like that, well then Trump just comes in with an answer.” Trump has gleefully exploited this dissonance in political language and the broader American political psyche. But there have been grave consequences to his success: People across the American political spectrum have suddenly found themselves homeless, appalled by either the cynicism or the excesses of their own side. Rubin’s show channels that confusion, even if it sometimes involves guests who amplify some of its causes.“We have to be willing to have hard conversations about important things,” Rubin says, “otherwise we just hand it to the easy-answer people. And there are a bajillion of them on every side.”***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Armin Rosen is a staff writer for Tablet magazine.