In 1982, after a series of increasingly high-profile radio gigs in suburban Westchester, Hartford, Detroit, and Washington, D.C., a scrawny, long-haired, 6’5”, 28-year-old Long Island native named Howard Stern, who had gained notoriety for his naughty-boy japery, was summoned to New York, the nation’s biggest radio market, to be the afternoon drive-time man at WNBC-AM, which then was NBC’s flagship radio station. Stern garnered big ratings—but, after three years, was fired by executives at 30 Rock who felt he was tarnishing the Peacock Network’s brand. Stern was promptly snapped up by another Big Apple station, WXRK-FM, or K-Rock, and during the next two decades served as its spectacularly popular morning man. (Meantime, WNBC-AM went rapidly downhill and, in 1988, was shuttered, along with the rest of NBC’s radio division.) Over the years, Stern’s show got syndicated to other major North American markets, and for a time, highlights from each day’s show were aired the same evening on the E! television network. In 2006, when Sirius and XM were competing to dominate the new medium of satellite radio, Sirius offered Stern a gigantic sum to be the centerpiece of its extremely wide range of programming, from the Catholic Channel to OutQ (for gays). The salary hike reportedly made Stern the highest-paid performer in show business, won Sirius millions of new subscribers, and before too long, sure enough, led to the absorption of a faltering XM into the behemoth that is now Sirius XM.

Fourteen years later, Stern can still be heard on Sirius—but much of what his listeners now hear doesn’t sound much like the Howard Stern of yore.

When he first came to New York, Stern was mostly a DJ—a spinner of Top 40 records. But he soon dropped the music entirely and instead spent his air time jabbering with his co-host and newswoman, Robin Quivers; engaging in gut-busting, and often exceedingly puerile, exchanges with his stand-up comic sidekicks, Jackie “the Jokeman” Martling (1986–2001), and, later, Artie Lange (2001–2009); relentlessly mocking his supposedly slow-witted producer, Gary Dell’Abate, and other members of his staff, who appeared regularly on the air; making prank phone calls; playing profane song parodies; taking calls from (and often getting into protracted arguments with) listeners; welcoming fans into his studio to take part in small-penis contests, Lesbian Dial-a-Date, and other such tomfoolery; and, since his show’s blue humor kept away most A-list movie stars, interviewing such offbeat recurring guests as aspiring showbiz nonentity Mark Harris (a youngish gay man who had wed the aged movie actress Martha Raye), Playboy cover girl Jessica Hahn (who’d won fame in the Jim Bakker sex-abuse scandal), and edgy comedians like Sam Kinison, Pat Cooper, Bob Levy, and Yucko the Clown (a foul-mouthed character created by comic Roger Black); and checking in by phone with members of the “Wack Pack”—a grab-bag of devoted fans, most physically or mentally disabled, whose lives revolved around Stern and whose eccentricities he milked for laughs. “Some,” I wrote in 2009, “might find Howard’s humor at their expense cruel; others might consider it radically inclusive. I can testify that it’s possible to feel both ways at the same time. . . . Sometimes it’s when Howard is at his most outrageous that I suddenly realize he’s also accomplishing something strangely moving and human.”

For years, Stern was an integral part of the lives of millions of New York-area commuters whose time in their cars he made not just bearable but fun. His secret was simple: when you’re headed for a workplace where you’ve got to spend eight or more hours being a sober professional, possibly fearing your colleagues and scraping to your boss, starting the day with a good-size dose of sheer juvenile nonsense can be healthy. Yes, Stern had critics: leftist anti-defamation groups called him racist, sexist, and homophobic; cultural conservatives condemned him as a pig who interviewed strippers and porn stars and talked without surcease about flatulence and masturbation. The answer to the charge of bigotry—leaving aside the fact that his sidekick, Quivers, was a black woman—was that he always had lots of black, female, and gay fans, some of them frequent callers. In the 1980s and early 1990s, when gay people were all but invisible elsewhere in the media, Stern’s gay fans appreciated being included in his tent. Stern, I’d argue, played a bigger role in vanquishing homophobia than Ellen DeGeneres and Will and Grace; in the same way, I’m certain that countless Stern fans stopped being racists because they loved Robin, a former nurse and Air Force captain with political views the precise opposite of what they expected from black people.

As for the strippers and porn stars, they were always a minor part of Stern’s show—and they weren’t the main reason why millions tuned in every day. People listened because Stern could make them laugh so hard that it hurt; because he could rattle on for an hour about almost any topic and somehow make it riveting; because he seemed incapable of dissembling about anything (though he exaggerated for effect about a good many things); and because every day he let loose about whatever was on his mind, or was getting on his nerves—his marriage, his bosses, New York traffic, the news—and his listeners could relate to all of it, and feel better for having heard their own frustrations expressed. Stern was a radio star, but he was one of them, routinely piercing the pretentious images of showbiz figures, from Rosie O’Donnell to Kathie Lee Gifford, whom he considered phonies.

Radio is the most intimate of media, and Stern was the most intimate of radio hosts, stripping himself naked, as it were, for several hours a day. (Though he griped constantly about his job, he obviously loved it: scheduled for four hours every morning at WXRK—6 am to 10 am—he soon began taking his show well past 10, and sometimes even past 11.) He was fascinated by himself, even as he was aware of the folly of his own self-fascination; he boasted of his own unparalleled and underappreciated genius but continually underscored what a neurotic mess he was, riddled with hang-ups and insecurities. When he crowned himself King of All Media, it was partly serious, partly self-mockery, and partly a way of ridiculing a business in which you could end up being known as, say, the King of Pop as long as you kept identifying yourself as such. Stern’s fans—some of whom, when they phoned in, would greet him with “Hello, My King”—both got the joke and bought into it.

They all knew his story, starting with his childhood, when, by his oft-repeated account, his super-liberal parents were the only white householders to stay in their small neighborhood of Roosevelt, Long Island, when its racial makeup altered almost overnight, making the pale, gangly geek a conspicuous target for schoolyard beatings by black classmates. Nor did it help when his family finally moved to Rockville Centre, a largely white Roman Catholic community, where he was bullied for being a Jew. He could easily have used such material to exacerbate racial and religious tensions, but in his hands, the story of his childhood suffering had the opposite effect: he mined it for humor in a way that universalized it, enabling listeners, of whatever background, to identify and to laugh together. Who hasn’t felt scared, alone, and vulnerable?

Like Mel Brooks, moreover, Stern was a master of dark humor, using comedy to cope with life’s terrors. When his wife miscarried, he figured out how to turn it into an improbably hilarious routine. Often he reminisced about his military service in Vietnam, where, he bragged, he once “took out a whole village” and specialized in killing children because he “wasn’t as tough as the other guys.” As his fans knew, Stern had never been in the armed forces—it was all fantasy, a private joke between him and them. One recurring bit was “Guess Who’s the Jew?”, on which the host, “Kurt Waldheim, Jr.”—a Nazi officer played with Teutonic gusto by show writer Fred Norris—would take calls from listeners who had to guess which of three celebrities was Jewish. (Though 100 percent Jewish, incidentally, Stern liked to tell clueless guests that he was only half Jewish: this, too, was an inside joke with listeners, the gag being that people might hate him half as much if they thought he was half Gentile.)

For years, Stern’s critics insisted that fans would soon grow tired of his schtick. Instead, his popularity kept soaring. His show was simultaneously #1 in New York and L.A. His two autobiographical books, Private Parts (1993) and Miss America (1995) were #1 best-sellers (and his book signings drew massive crowds); his autobiographical film, also entitled Private Parts (1997), opened at #1. Quivers, Martling, Lange, and Dell’Abate wrote best-selling memoirs, too. Yet though he became internationally known, Stern remained, above all, a New York fixture. The poster for his movie Private Parts featured a picture of a naked Stern with the Empire State Building covering his naughty bits. Long before The Apprentice made Donald Trump famous outside New York, he was a regular guest on Howard’s show—and a genuine friend. (Stern attended Trump’s wedding to his second wife, and Trump attended Stern’s wedding to his second wife.)

Trump and Stern bonded over two things: their love of beautiful women and their commonsensical world views. For even as he lampooned religious conservatives and organized religion generally (gags about the pope and Cardinal O’Connor were a show staple), Stern had no illusions about the Left. He stood up for hardworking family men; he believed in law and order; he respected the police and military; and he called out David Dinkins’s disastrous mayoralty as lustily as he later cheered Rudy Giuliani’s reforms. (In 1994, he won the Libertarian Party nod for Governor of New York—among his top issues was getting highway repairs done at night—but he withdrew from the race rather than comply with financial disclosure requirements.) During the O.J. Simpson trial, Stern derided those who doubted O.J.’s guilt, and on 9/11, watching the Twin Towers collapse from his studio window, he didn’t mince words about radical Islam. He recognized that he was lucky to be an American, and, while no expert in modern history, he was clear on the basics. When a German radio personality visited his studio, Stern played tapes of Hitler harangues and the Ride of the Valkyries; when a French broadcaster dropped in, Howard savaged his country for folding so quickly to the Nazis—and made fun of berets, to boot.

One anecdote demonstrates the extent of Stern’s influence in New York in those days—and illustrates the promptitude with which he could turn an unexpected, potentially tragic event into comedy. On December 8, 1994, he took a call from a Hispanic man who said that he was standing on the George Washington Bridge and was about to jump. To verify the man’s story, Howard asked that other drivers on the bridge honk their horns if they could see him. There ensued a chorus of honking horns. To keep the man from jumping, Stern riffed comically, telling him, for example, that if he leapt to his death he’d miss the movie adaptation of Private Parts. While Stern jested away, a listener named Helen Trimble spotted the would-be jumper from her car, pulled over, and put a bear hug on him to save his life. Within moments, cops who’d also been tuned in while crossing the bridge took the man into custody.

Once the man had been led off for a psychological evaluation, Stern, with his trademark combination of genuine egotism and self-mockery, launched into a preposterous spiel about what a hero he was; then, deciding that a show of modesty would be more becoming than self-congratulation, he shifted gears, maintaining that he wasn’t a hero while ordering Quivers—all of this on the air, of course—to keep insisting that he was. After fielding congratulatory phone calls from Senator Al D’Amato and former Mayor Ed Koch (both friends of the show), Stern held a press conference at which he delivered a comically absurd speech. “Now I know,” he said with faux solemnity, “how . . . a fireman feels pulling children from a smoke-filled building.” Stern noted that he had often been called a racist, but asked: “Would a racist pluck a Spanish brother . . . from a suicide plunge that would have left his wife and 18 children and 45 relatives homeless?”

In palpable awe at the way in which this rescue had transpired, Dell’Abate commented: “This show is like one big community. Everybody is listening.” It certainly could feel that way. Over the years, loyal Stern fans, like members of a family, became tied together by, among other things, a constantly accumulating, and ultimately encyclopedic, collection of inside jokes. Longtime listeners, for example, could tell you in detail the story of the day that Dell’Abate acquired the nickname “Baba Booey.” But that wasn’t all. Over time, fans who’d been drawn to Stern by his goofy antics found that they’d also developed a familial affection for him and his crew. In 2012 and 2013, Quivers did the show by ISDN hookup from her apartment, never missing an appearance and sounding as cheerful as ever. When she finally announced on the air that, after a 12-hour operation and 15 months of painful radiation and chemotherapy, she had, against all odds, just finished beating Stage 3 cancer, the toughest of Stern listeners were in tears, awed by her quiet strength, by her refusal, during all those months, to indulge in so much as a moment of on-air self-pity—and, not least, by her dedication to the show, which, she said, was the one thing that had kept her going.

I have mentioned the film Private Parts. That movie, directed by Betty Thomas and produced by Ivan Reitman, was, above all, a tribute to the patience and devotion of Stern’s then-wife, Alison, with whom he had three daughters. It was their home life, in an ordinary Long Island suburb, that proved the source of much of Howard’s humor—and audience identifiability. Four years after the film’s release, Howard and Alison, to everyone’s shock, divorced; some time thereafter, Stern began dating a leggy model named Beth Ostrosky, whom he wed in 2008 at the posh New York restaurant Le Cirque. Stern and Ostrosky now divide time between a Manhattan apartment he bought in 1998 for $4.9 million; a beachfront mansion in Southampton, Long Island; and a $52 million residence in Palm Beach. And they socialize with many of the same celebrities at whom he once scoffed and who viewed him as a vulgar D-lister. Many of his fans resented these changes, calling him “Hamptons Howie.” Writing in 2009, I defended him. “Howard’s fans have become spoiled,” I argued. “While they age, they want him to remain the same ambitious, energetic, irreverent young guy they first listened to when they were young.”

Alas, Howard wasn’t done changing. First Lange quit in 2009 (owing to a heroin addiction that he has only recently managed to kick), leaving behind a void in energy and edginess. Then, from 2011 to 2015, Stern sat as a judge on America’s Got Talent, a career move that baffled his fans: how could he put so much effort into such a vapid vehicle? He actually called AGT his “dream job” and often seemed to treat his radio program as little more than an opportunity to promote it. There were additional enigmas. Stern, who had once disparaged the awkward, embarrassing dance moves with which Ellen DeGeneres opened each episode of her daytime talk show, now claimed to find them enjoyable. While publicly making up with people like Rosie O’Donnell and Kathie Lee Gifford (“You’ve always been so nice,” he told Gifford; “you just pissed me off because you were everything I wasn’t”), Stern banned from his program veteran guests like the lewd, riotous comedian Gilbert Gottfried. Howard even refused to run ads on his show for one of Lange’s books. For years, Stern had battled with his bosses, and the FCC, over censorship; now he himself was sanitizing the vintage Stern shows that filled up most of the airtime on his second Sirius channel, Howard 102. (Howard 101 replayed his morning show throughout the day.) Increasingly, he focused on interviewing aging rock stars. He is, admittedly, a terrific interviewer; but many longtime fans, me included, weren’t all that interested in hearing, day after day, the detailed life stories of warhorses like James Taylor, Roger Daltrey, and David Crosby.

Then came the 2016 election. Stern had bonded with Trump for years, but had always considered himself a “Clinton guy,” though both Clintons had turned down multiple interview requests, and Bill had even snubbed him once at a party. Most of his FCC fines were levied during Clinton’s presidency. But in 2016, Stern supported Hillary. His explanations made no sense; he sounded like just another Manhattan liberal. (In one big way, to be sure, he was the same as ever: he was still fervently pro-Israel and capable of reading the riot act to BDS advocates like former Pink Floyd front man Roger Waters.)

In response to Stern’s metamorphosis, many longtime listeners peeled off. Eventually, bored by what his show had turned into, I became one of them. A whole sub-sub-genre of online entertainment has come into being: the interview with, or conversation between, former denizens of Stern World discussing the question, What happened to Howard? “He’s not the man I knew,” Lange told radio host Gregg “Opie” Hughes in 2016; in 2017, Lange described the Stern show as having done “a 180.” Many listeners agreed. Some blamed Ostrosky, saying that her desire to hobnob with A-list stars motivated Stern to clean up his act. Some pointed to Marci Turk, a woman whom Stern hired a few years back to make him, according to a 2017 Wall Street Journal profile, “just a bit softer as part of his strategy to get celebrity interviews.” Others have wondered about the role of his daughters. The oldest, Emily, born in 1983, became an Orthodox Jew and Torah scholar and told the New York Post in 2015 that her father’s on-air fixation upon sex had “kept me out of the dating ring” when she was younger and that she was “scarred” by her parents’ divorce and by her dad’s subsequent marriage to “a model.” The other two daughters, Debra (born 1986) and Ashley (born 1993), have maintained lower profiles. But all three have apparently gone to college and held various jobs, and one can imagine them, over the years, having teachers, classmates, employers, colleagues, friends, and beaux who, in one way or another, communicated to them the idea that they should be ashamed of their father. Perhaps they were ashamed, and perhaps he knew—and wanted to do something about it before it was too late.

Another theory, discussed by Lange and Martling on a recent podcast, probably contains at least a degree of truth: did Stern, during all those years when he was making fun of the crème-de-la-crème of the left-wing showbiz establishment, actually want to be one of them—and finally got so rich and famous that he knew he’d be welcomed into their ranks, if only he overhauled his act?

Now Stern has a new book out, his third. The first two were jokey, wacky memoirs interspersed with mini-essays about his staff members, favorite show guests, and celebrities he hated. Plus cartoons. Among his best guests, he wrote in Private Parts, was Trump, whose own comment about Stern was given the honor of being placed in a sidebar: “I tune in to Howard to hear what you rarely get these days—straight talk and very close to the mark.” Howard Stern Comes Again is, to put it mildly, a horse of a different color. A classy-looking, large-format, 500-plus-page collection of his favorite celebrity interviews, it’s patently intended to cement his new image as, above all, a serious interviewer of the first rank—and as a sometime bad boy who, thanks to thousands of hours of psychotherapy, has grown up. In his introduction, he writes that his principal reason for compiling this tome is his daughters: “I’ve always wanted them to be proud of the work I’ve done on the radio—and on myself.” While excerpts from his largely spicy, flippant interviews with Trump recur throughout the book under the snide heading “And Now a Word from Our President,” Stern pretends that Trump was never a friend—just a frequent guest. (“I’ve never had Donald over to my place for dinner or vice versa.”) And he makes this jaw-dropping claim: “As my listeners know, I don’t like talking about my political beliefs on the air.”

Mainly, he goes on at length about his “personal evolution,” asserting that his “view of the world has matured” and that “empathy, emotional openness, and a genuine curiosity about the beauty in the world have begun to develop.” (Note the clunky use here of the passive voice, as if he were quoting from his shrink’s notes.) He disowns his former “hard-ass pose,” which he diagnoses as having “provided an almost impenetrable shell that protected me from feeling need.” He even asks readers to do him a favor and throw out their copies of his first two books. In promotional interviews for Howard Stern Comes Again—the incredible number of which seemed to belie his claim that he’d found humility—he repeated this spiel. He once squeezed laughs out of his narcissism; his narcissism now takes the form of tiresome bragging about having purportedly surmounted it.

In any event, this latest round of interviews made for a sad spectacle. A great entertainer was disowning the best part of his oeuvre; a former rebel leader was bowing to the king to win favor at court; a master at skewering high-level hypocrisy had gone over to the other side. “You’ve gone from filth merchant to talk of the town,” Jimmy Kimmel told him in October. Stern’s opening commentaries on the interviews in his new book seem designed to make old fans wince: he considers Madonna “a kindred spirit,” calls Stephen Colbert “very evolved and emotionally connected,” praises Rosie O’Donnell for her “wisdom and graciousness,” applauds Lena Dunham for her “wisdom” and “understanding,” and touts Gwyneth Paltrow’s “humanity.” When Amy Schumer recalls the time her boyfriend touched her without explicit permission and hesitates to call it rape, Stern insists that it was, and concludes by saying, “I want to apologize for all men.” He even manages to work in a sympathetic word for Christine Blasey Ford. And the references to his own “personal growth” keep on coming. After a while, he sounds like someone who’s joined a cult.

Stern’s transformation reached its apotheosis when, on December 4, he welcomed Hillary Clinton into his studio for more than two hours. Even for a longtime fan who’d watched Stern’s persona shift over the years, I found the man who interviewed Hillary barely recognizable. Finally he was the shock jock he had always been accused of being—because his relentless flattery of the former First Lady was truly shocking. It was as if he were determined to prove that he could fawn over Hillary more fervently than her most ardent supporter. “My fantasy,” he told her, “was not only to meet you but to tell you what a hero you are to me. . . . You had the expertise I wanted in a president. . . . I wanted you to be president so bad.” He’d thought that hers would be “a spectacular presidency” because “she cares,” because she knew everything and everyone, and because she had “devoted her life to public service.” He agreed with her that Trump’s presidency has been a disaster and that Trump represents an existential threat to America. Once a hero of free speech, Stern criticized Facebook for not censoring Trump fans enough; one of Hillary’s problems in 2016, Stern told her, was that she had been “too truthful.”

Listening to this balderdash, you’d have thought that Clinton had led a saintly life, that she had been constantly set upon by jealous, corrupt inferiors, and that her career had been a spotless series of legislative and diplomatic triumphs. Buying into the notion of Hillary as a lifelong victim of the patriarchy, Stern seemed to be out to make up, in one interview, for every time he’d ever gotten a stripper to remove her top. One illuminating moment came when Stern praised Howard Zinn, the Communist author of A People’s History of the United States, a shoddy work of propaganda that has, alas, become a perennial best-seller and college text. Every Stern fan knows that Howard’s not big on books, so if he’s actually read Zinn’s opus, it’s likely his chief source of information on American history—a scary thought.

It was a stunning listening experience. When Hillary blamed James Comey (along with “the Russians and Wikileaks”) for her election loss, Stern went along with her, even though Comey had done Hillary a service by choosing not to prosecute her for clear violations of the Espionage Act. When she mentioned her emails, Stern didn’t bring up her private server or her destruction of the emails with BleachBit but instead agreed readily with her baffling claim that the emails had been “misinterpret[ed]”; when she criticized Trump’s “trade battles” and tax breaks, said that Trump was in Putin’s “camp,” and accused Trump fans (and not Antifa) of committing acts of violence around the country—and when she even knocked the booming Trump economy—Stern nodded along. He made no mention of Fusion GPS, the Clinton Foundation, her contorted version of the Benghazi episode, her dubious story about coming under fire in Bosnia, or anything else remotely scandalous in her (or her husband’s) past. Both Hillary and Stern took Joe Biden’s side in the Ukraine controversy and agreed that Trump’s famous phone call with the Ukrainian president had amounted to an “abuse of power.”

The entire interview was a case of kowtowing on an epic scale. Howard Stern, who rose to fame, in considerable part, by zapping fraudulent politicians, had now given one of the most sycophantic interviews of all time to a woman regarded by many as the most duplicitous pol of our era. It was a terrible comedown for a guy who’d earned a reputation for fearless honesty.

And yet, he’d apparently gotten what he wanted: now that he’d done this love scene with Hillary, was there any door in Manhattan or Malibu, the Hamptons or Hollywood, that could remain closed to him? Once the king of the outsiders, the voice of the deplorables, Howard Stern has become the ultimate insider, whom the likes of Cher, Madonna, Ellen, Rosie—you name it—would not only be eager to socialize with but also would look up to, as a top-ranking member of their cloistered club. For Stern himself, there could be no sweeter victory. For his legions of diehard fans—O, what a falling-off was there!

Photo by Larry Busacca/Getty Images for SiriusXM