Wenner was the fan he purported to be, but that was only one side of him. Though he walked in step with the counterculture, he was also a Kennedy-worshipping preppy whose thwarted ambition to attend Harvard had diverted him to Berkeley, a locus of left-wing radicalism where Wenner spent half his time with his nose pressed against the glass of high society. An inveterate social climber whom friends found so cocky as to be overbearing, Wenner crashed debutante balls and went on ski weekends to private resorts with rich and handsome friends who knew Kennedys and Hearsts. Keen to obscure his Jewishness, and his latent homosexuality, he chased after the sons and daughters of Old San Francisco—the children of local industry—as they migrated from the stolid precincts of Pacific Heights to pot-smogged Haight-Ashbury. Here was a breathtaking new freedom and opportunity, a world unhinged and made boundless by reality-smashing chemicals. “The freest generation this country has ever seen,” marveled Ralph Gleason, the music critic for the San Francisco Chronicle and Wenner’s mentor and co-founder in Rolling Stone. “No makeup, no bouffant hairdos, no button-down shirts and ties and no Brooks Brothers suits.”
Wenner imbibed the new values—sex and drugs and rock and roll—but they were folded into a larger pattern of aspiration. He understood that along with the drugs and freedom there was fame, and also money. As a teenager, he attended a boarding school in Los Angeles that housed the offspring of Hollywood royalty, including Liza Minnelli, with whom he waltzed at a school dance. Their sparkling pedigrees offered Wenner solace from his broken home life. To fit in, he carefully monitored and organized his classmates in the school yearbook and won their allegiance with a rogue newspaper he invented to advertise his popularity and antagonize the faculty. Journalism was his VIP pass to everything he could hope to be.
To speak to the kids who understood that the revolution had arrived in 1967—to speak to the kids who got it—required a voice in the same register and cryptography as Bob Dylan’s stoned telegrams, which Jann Wenner absorbed in lysergic waves with his head between two KLH speakers lying on his apartment floor in Berkeley. Wenner would later say he related to the Miss Lonely character in the seminal Dylan song “Like a Rolling Stone”—the female dilettante and object of scorn to whom Dylan is laying down his bitter education.
But Wenner was a quick study. He had an intuitive grasp of the most significant quality of the new rock audience: Unlike the one that fueled the British Invasion, it was largely male. For marketers, this new youth culture was uncharted territory, and Wenner was the pioneer. Until 1966, the primary outlets in America for the Beatles and the Rolling Stones were 16 and Tiger Beat, New York– based magazines for teenage girls who fetishized Paul and John and Mick and Keith as objects of romance and trivia. Wenner made it safe for boys to ogle their male idols as rapturously as any girl might by adding a healthy dose of intellectual pretense—a phenomenon that kicked into high gear with Sgt. Pepper’s Lonely Hearts Club Band, released five months before Rolling Stone appeared. “If James Joyce played the electric guitar he would probably have made an album like Sergeant Pepper’s Lonely Hearts Club Band,” wrote Wenner in a review pitched to High Fidelity magazine (and rejected as “pretentious guff”).
In one sense, Rolling Stone was a natural reaction to Sgt. Pepper’s, which signaled the emergence of full-length 33 ⅓ rpm albums as public statements to be fetishized and reckoned with—in effect, news from the youth front. The turning point was the Monterey International Pop Festival in June 1967, the convergence of new rock groups from London, New York, and Los Angeles for a media spectacle covered by every news outlet in America. It was arranged and produced by record men from Los Angeles and promoted by the erstwhile press secretary for the Beatles, who conscripted Jann Wenner to write publicity material. By courting the record men who knew next to nothing about what the San Francisco kids were doing and saying in private, Wenner was perfectly positioned as a go-between, connecting the counterculture of Haight-Ashbury—which every head in America now looked to for cues on LPs, politics, dope, and sexuality—and what was then known as the straight world. The two were already on a collision course, but Wenner, more than anyone else, catalyzed the process. “The business world, which was represented by the record companies, was just so old-fashioned and foreign,” said Wenner. “They reluctantly came to rock and roll.”
In creating Rolling Stone, Wenner borrowed heavily from a short-lived biweekly newspaper called The Sunday Ramparts, where Wenner worked until it ceased publication in June 1967. After Monterey, Wenner hustled up $7,500—the largest chunk from Jane’s father, a Manhattan dentist—and simply recycled the defunct paper, an adjunct of Ramparts magazine, as his own. The printer didn’t have to change the settings on the Goss Suburban press machine to spit out Rolling Stone, and Wenner even recycled the design and layout, a parody of stuffy British newspapers like The Times of London. The first issues had a primitive simplicity, but the clean lines and functional columns looked audacious next to underground papers like Crawdaddy! or the San Francisco Oracle, which defied convention with willfully amateurish layouts. By contrast, Rolling Stone was thoroughly commercial: The Fleet Street fonts and pin-striped lines of the original Sunday Ramparts were created by an advertising agency founded by Howard Gossage, a pal of Tom Wolfe and Marshall McLuhan who produced print ads for the Sierra Club and Rover cars. (The designer was a woman named Marget Larsen.)
It was this—the radical conventionality of Rolling Stone—that was Jann Wenner’s most important innovation. When he stamped the whole package with a psychedelic logo designed by poster artist Rick Griffin—the curled ligatures and looping serifs unmistakable signifiers of dope-peddling head shops on Haight-Ashbury—he instantly legitimized and mainstreamed the underground.
From the vantage of a swivel chair in a warehouse loft on Brannan Street, Wenner and his “little rock & roll newspaper from San Francisco” brought first-name intimacy to the scene. For the first issue, he simply drove across town to the Haight-Ashbury to interview the Grateful Dead in their living room and help publicize their arrest for pot possession. Keyboardist Ron “Pigpen” McKernan hoisted a rifle for the photo op—a triumph, a gleeful dare. “All the news that fits,” Wenner put above his title, tweaking the East Coast’s central journalistic institution. And his headlines declared it so: “A New Beatles Movie!”; “Eric Burdon Quits the Animals!”; “Jim Morrison Exposed!”; “John and Yoko Rock Toronto”; “Chicago 7: Youth on Trial”; “Paul McCartney Gets Back”; “Bob’s Back!”
In 1967, it was still a radical idea to publish college-educated intellectuals like Jon Landau and Greil Marcus opining on James Brown or the Jefferson Airplane as if it were serious art, like jazz. “Though he didn’t invent serious pop criticism, Jann was the one who popularized it,” observed Mick Jagger, whose band had been playing to teenage girls for five years when Rolling Stone began. “There were magazines before, and criticism before, but the magazines were a bit fly-by-night and they weren’t taken seriously. But this was a whole magazine about it that was dedicated to semi-serious criticism.”
As far away as London, mods and rockers alike started passing Rolling Stone around. Suddenly Jagger knew Jann Wenner’s name—the San Francisco kid with the chutzpah to name a magazine after his band and then trash his latest record. Bob Dylan was sent a letter from Wenner asking him to write a story for a new magazine named after his six-minute radio hit. Wenner printed every last utterance of Pete Townshend of the Who—an interview recorded at Wenner’s apartment on Potrero Hill in the spring of 1968—as if it were an exclusive with God on the second day of creation. Twelve pages over two issues, some sixteen thousand words. Townshend loved it. And for eighteen-year-olds fretting over the draft and blowing pot smoke out their bedroom windows between sides