Joe Hagan has written what promises to be the standard biography of Jann Wenner—standard, because it’s hard to imagine anyone working up the energy to take another stab at it. Fifty years ago, at the age of 21, Wenner founded Rolling Stone magazine, and he’s been editor in chief ever since. Thanks to the anniversary, he has lately been much in the news. Not only has Hagan’s very long biography appeared, but so has a coffee-table book, 50 Years of Rolling Stone, a slab of self-congratulation recounting the magazine’s most celebrated articles and writers, with a not-humble introduction by Wenner. He has made the rounds on the chat shows, morning and evening. HBO, meanwhile, is airing a two-part, four-hour documentary, Rolling Stone: Stories from the Edge, produced by Wenner and codirected by the gifted left-wing documentarian Alex Gibney. Altogether it is enough commotion to cause the average consumer of media to rear back and ask: “But why?”

As it happens, there are at least two answers to that question. One is that Wenner possesses superhuman powers of self-promotion. In the journalism business, it is usually the writers who leap onstage to gyrate and shimmy in hopes of pleasing an indifferent public, while their editors keep shyly to the shadows, feigning modesty and smoldering with envy. Not our Jann. He has made himself more famous than all but a handful of his writers; the rest bear on their backs the skid marks from his powder-blue 1963 Porsche 1600-N Cabriolet.

The other answer is this: Wenner was a genuinely great editor, and as with all great editors his magazine was an extension of his ambitions and enthusiasms. Rolling Stone and its founder are worth attending to, if not celebrating, because for two or three decades the magazine served as the most articulate promoter of the 1960s counterculture in all its guises: sexual, political, musical, and artistic. By now, of course, the counterculture has dropped the “counter” and assumed dominance over every significant American institution short of the Mount Vernon Ladies’ Association. Wenner’s instincts told him where everybody was headed, whether they knew it or not, and he hopped to the front of the parade. As a result he became not only famous but rich—and not just rich but shamelessly, ostentatiously rich, a man who enjoyed his filthy lucre perhaps a bit too much. (The powder-blue Porsche was just the beginning.)

And many of his early allies, who once considered him a fellow radical, have never forgiven him for it. Hagan, a magazine writer who once interned for Wenner, seems as preoccupied with the ebbs and flows of his subject’s net worth as Wenner is. It’s said that most biographers come to loathe their subjects sooner or later, on the principle that no man is a hero to his valet, and the trick is for them to claw their way back to some measure of toleration, if not affection or respect. Hagan fell into contempt and couldn’t climb out. Aside from an occasional nod to his editorial gifts, the biographer never gives Wenner an even break.

A quick flip through the index shows the story as Hagan wants to tell it. Under the heading “Jann Wenner” we find: celebrity worship of; driving ambition of; establishment espoused by; as exploitive and opportunistic; narcissistic self-importance of; relationships betrayed by; wealth, status, and power pursued by; authoritarian managerial style of; weight control issues of . . .

And then the lowest blow of all: Trump compared with . . .

The biographer lobs insults into the oddest places. After the death of one of Wenner’s contemporaries, Hagan tells us that “death always had a dramatic and transformative effect on Wenner,” which places Wenner on the side of roughly 99.9 percent of all the human beings who’ve ever lived. But Hagan follows up with a quotation from an estranged ex-employee to make a dark non sequitur: “Jann loves death.” There are lots and lots of estranged ex-employees, happy to squeal on or off the record. Hagan likes sarcasm, too. After describing some instance of Wenner’s posh lifestyle, for instance, he sniggers: “A street-fighting man indeed.” Burrrrrrn.

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The biographer’s contempt is more than offset by the puffery of the HBO film and the 50 Years book. Anyone who takes the trouble can piece together a balanced and more plausible view of Wenner with snatches from each. Like most success stories, his begins in ravenous ambition. Reared in prep-school comfort in Los Angeles, Wenner had dropped out of UC Berkeley and was working a series of low-end reporting jobs in San Francisco when he got the idea for Rolling Stone. According to his inaugural editorial, it would be a magazine “not just about music but also about the things and attitudes that music embraces.”

That scope—going beyond rock and roll to the larger cultural changes it symptomized—was crucial to RS’s success; up to then magazines devoted to pop music operated on the fanzine level of Tiger Beat. As co-conspirator and éminence grise, Wenner enlisted Ralph J. Gleason, 30 years his senior. Gleason was a widely admired jazz critic who himself had become besotted by rock and roll. His fascination led him to make the sartorial mistakes common in those days to the 50-year-old men who embraced rock culture and, they hoped, the young women who came with it. At Rolling Stone he dropped the hipster duds and acquired the bushy sideburns, the billowing mustaches, the turtlenecks, the peace symbols dangling here and there.

Still, Gleason was a serious man. He had just made the case for rock’s artistic significance in a long, learned, and rather pompous essay that would appear in the American Scholar, of all places. This was 1967, the year of Sgt. Pepper. Like Wenner, Gleason believed that as a musical form rock was substantial enough to bear the critical weight that hep-cat intellectuals had earlier placed on jazz. Unlike Wenner, he had a keen appreciation for professionalism. Gleason tempered his young colleague’s youthful exuberance and wit—the magazine’s self-mocking motto was “All the News That Fits”—by insisting they meet printers’ deadlines, stick to a regular editorial schedule, set up a system for fact-checking, and hire real reporters rather than deep thinkers. The first issue contained a grown-up exposé of the sketchy financing of the recently concluded Monterey Pop Festival, an event that even the straight press was celebrating as a hippie idyll. Popular music journalism had never seen anything with the heft and ambition of Wenner’s magazine.

From the first, Hagan makes clear, Wenner was as much a fanboy as a journalist, hoping to use his position as editor of a rising publication to bathe in the nimbus of his favorite rock-and-roll celebrities. The ambition often paid off editorially. Wenner’s obsession with John Lennon led to other early scoops and made Rolling Stone seem indispensable to anyone following the counterculture. In 1968 word came that Lennon and Yoko Ono had posed naked, front and back, for the cover of a new album called Two Virgins. After Wenner’s relentless transatlantic hectoring, Lennon agreed to license the photos to Rolling Stone, if only because no one else would take them. (Asked about the significance of the Two Virgins cover, Lennon’s bandmate George Harrison said everything that needed saying. “It’s just two not-very-nice-looking bodies,” said the Quiet Beatle. “Two flabby bodies naked.”) Wenner put the flabby backsides on the magazine’s cover and tucked the other, full-frontal photo inside. It made a worldwide sensation. Multiple printings of the issue sold out. “Print a famous foreskin,” Wenner said, “and the world will beat a path to your door.”

And Wenner had made a new friend. The HBO documentary gives Homeric treatment to the relationship between Wenner and the Lennons, from foreskin to aft. The friendship was transactional, as friendships between journalists and celebrities usually are. Lennon had a constant need to generate publicity, especially for the new commercial entity known as “John and Yoko,” and Wenner craved proximity to a Beatle. A few months after the Beatles broke up, Lennon agreed to grant Wenner a long interview. Coming off years of drug abuse and months of psychotherapy, Lennon was as garrulous as any ex-junkie analysand could be.

He hammered his former bandmates personally and musically and careened from self-adulation (“If there’s such a thing as [a genius], I am one”) to self-loathing (“the Beatles are the biggest bastards on earth”). The interview, its extravagant profanity uncensored, appeared over two issues and again generated headlines everywhere. In his nationally syndicated column William F. Buckley Jr. referred to the interview as “How I Wrecked My Own Life, and Can Help Wreck Yours.”

By this time Wenner was presenting himself as an intimate of the couple—such good pals indeed that Lennon bestowed upon him a pen-and-ink drawing of Yoko, naked with legs akimbo. The Lennon association gave Wenner and his writers credibility as they set out to woo other stars for profiles and interviews. The intimacy was surely exaggerated, but in any case it didn’t last long. Lennon quickly came to regret the interview with its multiple indiscretions, and he assumed that its one-time appearance in Rolling Stone would be the end of it.

He assumed wrong. Wenner knew editorial gold when he saw it. After promising Lennon never to reissue the interview in book form, Wenner waited a few weeks and then incorporated his own book-publishing company to reissue the interview in book form. Furious, Lennon never spoke to him again and badmouthed him to anyone who would listen. Hagan says Lennon quietly funded a rival countercultural magazine in San Francisco in hopes of driving RS out of business. By then it was too late.

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S tories from the Edge, the HBO documentary, fails to mention the falling out between Jann and John, leaving viewers with the impression of an enduring friendship. Presumably the filmmakers omitted the rupture because it was caused by Wenner’s duplicity and avarice, which soon became his favorite tactics as a businessman. Yet even discounting for the whitewash, Stories from the Edge persuades a skeptical viewer that Wenner had his own kind of integrity. The fanboy in him ran puffers on his rock-star friends, but as the magazine grew in circulation and seriousness the editor in him knew enough to print the facts as his reporters found them.

The magazine’s first impressive act of journalism was a meticulous re-creation of the Rolling Stones’ Altamont music festival in late 1969, where four people died, one of them in a murder committed a few feet from the stage while Mick Jagger crooned “Sympathy for the Devil.” (“We always have something very funny happen when we start that number,” he reportedly said.) The Rolling Stone article placed blame for the calamity squarely on the Stones, even though Wenner at the time was sucking up to Jagger like a DustBuster. In the same way, while Wenner might occasionally insist on a favorable review of some performer he was busy romancing, the list of albums by big stars that he let his writers pan is long, and surprising even now. The Stones’ Sticky Fingers and Exile on Main Street; Crosby, Stills, Nash, and Young’s Déjà Vu; albums by U2; and nearly every note of music released by Led Zeppelin (“the limp blimp”) were slammed at their debuts.

Jann Wenner in 1977. [Jean Pigozzi]

The magazine was indelibly Wenner’s, but he didn’t mind surrounding himself with witty and independent minds. Often he let his staff mock his pretensions or politics in print. The editor of the magazine’s Random Notes gossip column once got so sick of Wenner inserting plugs for his pal Mick that he wrote up an entire column with nothing but references to Jagger—his name boldfaced no fewer than 26 times. Wenner saw it, thought it was funny, and let it run, including the thinly veiled reference to him as part of “the rising tide of groupieism which has widely affected the journalistic community.”

If you concluded from this freewheeling atmosphere that the people who worked for Jann Wenner liked him, you would be misled. Ten years ago, when former and current staffers held a 40-year reunion, they decided not to invite him so everybody could have fun. Many paragraphs in Hagan’s book simply dissolve into a mess of unflattering quotes from former employees. A lot of the enduring animosity is rooted in Wenner’s habits of betrayal and disloyalty. Wenner is one of those bosses who’s careful to aim his micturition downward, never sideways or up. Hagan gathers enough evidence to make the case that his subject is petulant, self-centered, miserly, cold-blooded, infantile, and quite willing, in the wink of an eye, to turn friend, family, or foe into objects to be manipulated for his own advancement or satisfaction. Not a lot of fun to date, work for, marry, have sex with, parent, be raised by, or do business with, is Jann Wenner.

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But what about his work? The editor that Wenner is most often compared to—by Hagan, by journalism professors, and by Wenner himself—is Hugh Hefner. The comparison is probably unavoidable. Both men singlehandedly founded famous magazines in the second half of the 20th century that shambled, still upright but much the worse for wear, into the 21st. Both men became famous for the polymorphous perversity of their (semi-)private lives. Wenner, Hagan writes, told an employee in 1973 that “he had slept with everyone who had ever worked for him,” men and women alike, and Hefner . . . well, we know enough about Hef already.

Professionally, though, the comparison is inapt and unfair—to Wenner. Hefner was a humorless flesh-peddler, a pompous publicist. His method of editing was to pay high fees to first-rate writers who sent him their third-rate stuff. It’s an impressive achievement: Over more than 60 years Hefner managed to edit a magazine whose contributors included Nadine Gordimer, Marshall McLuhan, John Updike, Vladimir Nabokov, Eric Hoffer, and John Cheever and still failed to publish a single landmark piece of fiction or journalism.

Not so with Wenner and Rolling Stone. As an editor Wenner was panoptic, widely curious, and tuned to talent. He discovered writers (Cameron Crowe, Joe Klein, Tim Ferris, Joe Eszterhas, Jon Krakauer) and revived writers with stalled careers (Greil Marcus, Hunter S. Thompson) and bought up writers (Tom Wolfe, P. J. O’Rourke) in the fullness of their prime. He squeezed all of them for their best stuff, through charm, cajolery, and cash. His greatest gift to them, aside from bottomless expense accounts, was patience, bordering on indulgence.

There are two kinds of writers, someone once said: “putter-inners” and “leaver-outers.” As an editor, Wenner was a putter-inner. Many of the magazine’s most famous articles ran to 30,000 words, at a time when an average cover story in Time or any other middlebrow title might top out at 3,500; the Lennon interview, for instance, was 36,000 words (about half of them were f*ck). An issue of Rolling Stone in its glory days offered vast hectares of prose, printed in stately columns with neoclassical trimming, marching down the page between illustrations of the highest quality (photographs by Baron Wolman, Richard Avedon, and Annie Leibovitz; pen-and-ink grotesques by Ralph Steadman; caricatures by Philip Burke and Steve Brodner). Imagine if the New York Review of Books had hired a slightly stoned Edwardian fop as art director and you’ve got the look of Rolling Stone at its point of highest development.

Annie Leibovitz signs a copy of the issue of 'Rolling Stone' that has on its cover her photograph of Yoko Ono and a nude John Lennon, taken just hours before Lennon was shot to death. [Logan Fazio/Getty]

The kind of latitude Wenner allowed his writers might have resulted in one of the dullest creatures in publishing: the so-called “writers’ magazine,” which is to say, “not a readers’ magazine.” If Wenner’s experiments in editorial indulgence were occasionally failures, at least they were noble ones. And they reflected a high opinion of his audience, maybe undeserved. In the HBO documentary, Tom Wolfe says, “In an era in which young people were supposed to have [the] shortest attention spans,” Rolling Stone “started running articles that were endless.” Elsewhere Wolfe has called Wenner the best editor he ever had, and it’s true: In a long and dazzling and multifarious career he produced his best work for Wenner’s magazine.

It was Wenner who sent Wolfe to Cape Canaveral in 1972 to write about a moon launch. When Wolfe came back with a different story—a long look at what made the first generation of astronauts extraordinary, titled “The Brotherhood of the Right Stuff”—Wenner understood what he had, and the book that grew from the piece and its sequels, The Right Stuff, is an indispensable work of Americana and of narrative journalism. A decade later, Wolfe got stuck trying to write a novel about New York City. Wenner offered to publish the book in installments, Dickens-style, on the hunch that the greatest magazine writer of his time might force himself to write against an immovable deadline. “I found the only marvelous maniac in all of journalism willing to let me do such a thing,” Wolfe says in 50 Years. The money helped, too—nearly $500,000 in today’s dollars, for a year’s worth of biweekly installments. The Bonfire of the Vanities, revised and placed between hard covers, caught American life more precisely and hilariously than any other novel of the time—or of our time, for that matter.

The writer most associated with Rolling Stone, and Wenner’s greatest editorial conquest, was Thompson, who went to work for him, after a fashion, in 1970, in what looked like another detour in a middling, itinerant career in newspapers and magazines. His first piece, about his own campaign for sheriff in his hometown of Aspen, Colorado, was extremely funny, but the next, “ Fear and Loathing in Las Vegas,” was a rocket launched into the uncharted stratosphere of magazine writing. We read in 50 Years that the article, and later book, became “a defining literary experience for several generations of readers,” and while “several generations” might be an overstatement, it’s no credit to our 1970s educational system that book-minded kids who couldn’t tell you where “Call me Ishmael” came from could recite the first line of “Fear and Loathing” in their sleep: “We were somewhere around Barstow on the edge of the desert when the drugs began to take hold.”

Hunter S. Thompson in 1970. [David Hiser]

Wenner turned Thompson into a brand, long before it occurred to anyone else that a self-respecting writer would put up with such an indignity. They called it “gonzo” journalism, and the word is still overused. His editor thought Thompson’s range as a writer was limitless. And Wenner might have been right—we’ll never know. Because Thompson liked politics, Wenner sent him out in 1972 to stalk the hapless gang of Democrats who were competing for the party’s presidential nomination and the chance to get creamed by Richard Nixon in the fall. (Wenner already had one writer, Timothy Crouse, covering the campaign. Why not two? Crouse’s coverage became another classic of American political writing, The Boys on the Bus.) Thompson filed 14 dispatches in all. For anyone who swallowed them whole as they appeared, and who never quite recovered from the experience, the story of their publication seems heroic, even oddly moving.

After a few days reporting, Thompson typically would hole himself up in a hotel and postpone writing for as long as possible—he once compared his method to a jackrabbit on a highway, waiting till the last second to jump out of the way of the car. At last, fortified with bourbon and methedrine (often supplied by Wenner), he might begin his story in the middle or at the end. He sent the sections as they rolled from his typewriter, out of sequence and at all hours, across a Teletype-like device to the RS offices in San Francisco. With the deadline pressing in, Wenner and a deputy would man the machine round the clock, and as the pages tumbled out they tried to arrange them into a coherent whole. “This looks like an ending here,” an editor would say, while Wenner fished around for transitions and a beginning.

“ Fear and Loathing on the Campaign Trail in ’72,” like its predecessor from Las Vegas, is a masterpiece of a kind. But what kind? The prose moves at lightning speed, tossing off wild images and wacky observations as it races down the page. Whatever it is, it’s not journalism. Long stretches of the book are simply made up, a fact that Thompson and Wenner assumed readers would tumble to. The rest comprises energetically written bits of mediocre, and ultimately mistaken, punditry, with intimations of an onrushing apocalypse as a backdrop to the fireworks. Indeed, it’s fair to say that the closer Thompson got to conventional journalism, the less interesting he was. In the end it didn’t matter that he invented so much of his material. Grand claims are still made for Thompson’s genius, but at bottom he was a clown, a humorist of the highest order, in the grip of mania. His enduring gift to his readers was to make them laugh. Which should be enough.

Thompson was once asked whether any other editor would publish writing like his. “Probably,” he said, “but they wouldn’t pay for it.” Thompson was well paid, especially after Rolling Stone made him famous and he could give college speeches at $20,000 a toss. Money was always a point of contention between Wenner and Thompson. (You could plug the names of any writer and editor into that sentence.) The disputes got personal as Thompson’s long, steady decline began, shortly after his campaign book was published in 1973. Until his suicide 32 years later, his stuff appeared only sporadically in Rolling Stone—or anywhere else. The booze dragged him down and down. For all his trademarked talk about his prodigious intake of exotic drugs—his packing list for Las Vegas: “two bags of grass, 75 pellets of mescaline, five sheets of high-powered blotter acid, a salt shaker half full of cocaine, and a whole galaxy of multicolored uppers, downers, screamers, laughers . . .”—the evidence suggests Thompson’s real problem was not much more than a roaring case of garden-variety alcoholism; the drugs were a way of keeping him awake so he could drink more. But such an admission would cripple the franchise. How could the man who invented gonzo suffer from something so . . . ordinary?

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In retrospect, despite his celebrations of anarchy and chaos, Thompson’s politics were pretty conventional too. His ideal presidential candidate was Jimmy Carter. The same can be said about Wenner, who is best described as a reliably liberal Democrat, with a few leftward feints—he wants to abolish all drug laws, for example. Politically, he doesn’t have a revolutionary bone in his body. This is why so many of his critics, including former allies of a radical bent, have despised him. No one can hate a liberal like a leftist. It’s also why, paradoxically, he and his magazine were able to escort the sixties revolution into its final, decadent, triumphant phase.

The HBO documentary shows a clip of the writer Robert Sam Anson in the 1970s, lamenting the wasted opportunity. “ Rolling Stone should be by its existence somehow threatening to the establishment,” he said. Instead, “it’s become the establishment.” Wenner happily agreed. That was the whole point! “Now we are the mainstream,” he announced at the magazine’s 10th anniversary. He moved the magazine from its old digs in San Francisco’s warehouse district to custom-designed offices on Fifth Avenue in Manhattan overlooking Central Park. He had hoped to become the establishment, he said, because he wanted to “change things.” But it was only now that he had reached the top that it became clear which “things” were supposed to change and which things were just fine as they were.

Just part of the establishment now: Jann Wenner (left) hanging out with Arianna Huffington and then-New York City mayor Michael Bloomberg in 2010. [Patrick McMullan / Getty]

True-blue leftists like Anson—like the early staffers at Rolling Stone—thought the sixties revolution was a package deal: Along with the sex, drugs, and rock and roll, we were supposed to get a leveling of the class system and a centralization of the economy, requiring nothing less than a frontal attack on the elites. Wenner was able to separate the elements, take what he liked—the sex and the drugs—and leave the rest, mostly the politics, as talking points. If he challenged the old elites, it’s not because he wanted a classless society. It’s because he wanted to take their place. And he did, and then watched as the rest of the ranks, in media, university departments, the boardrooms of private foundations, were filled with baby boomers like him.

The key to the boomer elite has been rhetorical egalitarianism and functional elitism. Wenner wore his liberal opinions like a flak jacket, and the magazine struck all the proper poses. From the early ’80s to the late ’90s, his national-affairs correspondent was a veteran journalist named William “Good Writer” Greider, an elegant stylist who pressed the virtues of statism into the heads of the few people who read any of the 200 columns he wrote. The present national-affairs columnist, a man named Matt Taibbi, lacks Greider’s elegance but is just as economically illiterate. (In the HBO documentary Taibbi compares himself favorably to Hunter Thompson. He is mistaken.)

Meanwhile, you could find Jann lounging at one of his Manhattan townhouses, flying in his Gulfstream to have dinner in Paris, or partying in the Hamptons with the local white trash—Michael Douglas, David Geffen, Ahmet Ertegun, Diane von Furstenberg, Barry Diller, various combinations of Kennedys and Clintons. He dutifully gave money to Democratic candidates, as a kind of cover charge. The boomer ruling class proved that capitalism-for-me, socialism-for-thee was in fact a viable social strategy. You could rail against income inequality even as you were buying a warehouse for your collection of antique roadsters.

It’s an old story by now, the hypocrisy of boomer liberalism, and I’m sure millennials can’t wait to see the last of it—the generation of feminists who forgave goatish politicians so long as they defended abortion on demand; or the environmentalists who burned a year’s worth of fossil fuel flying their Gulfstreams to global warming conferences; or the scourges of the uneven distribution of the nation’s wealth who took their income as capital gains so it would be taxed at a lower rate. Wenner showed them how to pull it off with a clear conscience; he built his magazine as a kind of roadmap. In Rolling Stone you could become outraged over the greed of other people— RS’s massive investigative articles always had the same villains (businessmen) and the same victims (noble working folk)—and still linger over the ads for a customized Rolex or that charming new resort in Aruba. You could have your cake and eat it too. Expressing the proper opinions made it possible, so long as they didn’t get out of hand.

Of all the stories told about Wenner and his magazine in this year of celebration, I savor one most of all, because it captures so well the view of politics that has allowed him and his peers to thrive. In 2004, Wenner’s old friend John Kerry won the Democratic nomination for president. He was challenging the unspeakable George W. Bush. The country’s future was at stake. With his new friend Larry David, the TV star, Wenner resolved to leave the comforts of home, put himself on the line, and hit the trail to campaign for Kerry—on Martha’s Vineyard.

The Wenner-David mobilization was a spectacular success. Kerry won the Vineyard in a landslide.

Andrew Ferguson is a senior editor at THE WEEKLY STANDARD .