It was an outrageously confident promise: “See and hear more great stars in one weekend than most people see in a lifetime,” declared ads for the first ever Playboy Jazz Festival. But the three-day August 1959 event more than delivered.
The brainchild of Hugh Hefner, the first jazz festival was part celebration of Playboy’s five-year anniversary and part marketing strategy, a way to raise the magazine’s profile and stake out cultural territory. The powerhouse lineup featured such first-ballot hall of famers as Dave Brubeck, Dizzy Gillespie, Louis Armstrong, Duke Ellington, Count Basie, Coleman Hawkins, Nina Simone and Sonny Rollins. Five concerts showcased more than three dozen acts, and the cheap seats cost a little more than a buck. That August weekend Playboy had taken the first step in creating what would become one of the liveliest and longest-running jazz festivals in America—though two decades would pass before it took the second step.
From the introductory issue of Playboy in December 1953, jazz had supplied the soundtrack. It was one of four topics Hefner suggested his readers would enjoy discussing with women—Nietzsche, Picasso and sex being the others. In 1957 the magazine introduced an annual reader’s poll of the hottest jazz acts and released vinyl collections featuring the winners. Music reviews and ads for hi-fi systems and the newest releases from Gerry Mulligan and Charles Mingus abound in early issues. “Jazz is the most personal of arts,” Hefner declared, “and, if we bring our passion to it, we are rewarded.” For Hefner, that passion demanded a living, breathing outlet.
But the festival faced a crisis before it was even under way, recalls Dick Rosenzweig, who in 1958 had begun what was to be a nearly 60-year career with Playboy: “We got a call from the mayor’s office. They informed us that they were sorry, but we could no longer hold the festival outside at Soldier Field.” Moving quickly, the Playboy team secured the Chicago Stadium, an enclosed, air-conditioned arena. “It rained like hell that weekend,” Rosenzweig says. “So thank you, Mayor Daley.”
The festival opened Friday night with 33-year-old trumpeter Miles Davis at the height of his powers, spinning elongated soul on Kind of Blue’s “So What?” alongside alto saxophonist Cannonball Adderley. Playboy donated the proceeds from the evening to the Chicago Urban League, a civil rights organization. Vocalist trio Lambert, Hendricks & Ross put the perfect ring-a-ding swing on Saturday night, while Ella Fitzgerald closed the weekend with a spirited “How High the Moon,” leveling the crowd with blasts of nimble scatting. (It had taken $10,000—twice the amont any other performer earned that weekend—to land Fitzgerald.)
Billboard declared the event an “overwhelming success.” The musicians and crowds were happy, and the magazine was elated. Nearly 70,000 tickets had been sold across the three days. Ambitious plans for a 1960 jazz fest—one that would take place in three cities—were discussed, but nothing materialized. “We were in such an expansive and go-go mood, there was only so much we could do,” says Rosenzweig. “We were constantly busy doing other events and promotions.” The first Playboy Club, for example, opened in Chicago in 1960, and locations around the world soon followed. With distractions like that, it’s no wonder the festival went quiet.
In the early 1970s Hefner bought Playboy Mansion West and began to spend more time in Los Angeles. When he finally decamped from Chicago to the West Coast, he brought his love of jazz with him. So when the magazine’s 25th anniversary rolled around in 1979, what better way to celebrate than to revive the jazz fest, 20 years after its original incarnation?
On June 15, 1979, the revitalized Playboy Jazz Festival, now a two-day affair, kicked off on the Hollywood Bowl’s iconic half-dome stage. Local promoter Darlene Chan produced the event. “I put all the elements together,” she says—everything from booking talent to coordinating lights, sound and transportation. In the two decades between the first and second jazz festivals, much had changed within the jazz world, but Chan and her staff crafted a remarkable lineup that included Benny Goodman, Sarah Vaughan, Art Blakey and Herbie Hancock. Acts that leaned outside the jazz world—such as Joni Mitchell, who played tunes from her collaboration with Mingus—signaled that the fest would be musically inclusive.
For almost 40 years the festival has presided over rain-free weekends at the Bowl, with Chan working behind the scenes every year. It has become the unofficial start of summer in L.A., a weekend when the hardest part can be trying to keep up with the rest of the attendees. A vast range of jazz acts (Tony Bennett, Ornette Coleman, Dianne Reeves), world music artists (Hugh Masekela, King Sunny Ade) and pop outfits (the Roots, Common, Ozomatli, Sheila E) have all performed tight 50-minute sets. The crowds are huge and energetic, often enlivened by the contents of their picnic baskets—one perk of the Bowl is that patrons can bring their own food and drink. Across its hardwood benches, stadium chairs and intimate box seats, the Bowl can accommodate 17,500 revelers. The summer sun slowly works its way to the back of the amphitheater, a peak glow nestling into the dinner hour.
Ten-time Grammy-winning guitarist and vocalist George Benson has been a frequent performer, occupying that perfect position between instrumental virtuosity and tender R&B suavity. A natural and engaging frontman, Benson knows how to entertain both the champagne sippers in the front and the Jell-O shot pounders in the back of the house.
“In a large place like the Bowl, you’re trying to reach that person way out in the last row,” Benson says. “In a little room, they hear you and feel what you’re doing. To get that sound out to the last row in the Hollywood Bowl, that’s difficult. It’s not just the sound system; it’s how you play what you play and the selection of the materials. You have to find the spot.”
The festival has grown into an institution, showcasing some of the most significant jazz musicians of the past half-century. It also fosters up-and-coming talent. Inviting young performers to fill the opening time slots has become an enduring tradition. And as L.A.’s largest jazz fest, playing it serves as a measure of success for local artists.
Bassist and singer Miles Mosley, a member of the trailblazing West Coast Get Down collective, first played the festival with his high school band in the late 1990s. Last year Mosley had his own festival berth, leading his chameleonic soul band through a set of songs indebted to the City of Angels. For him, it was the fulfillment of a childhood dream. “The Playboy Jazz Festival is the pinnacle of what you seek to attain as a kid looking at your musical heroes,” he says. “The first time that stage turns around and you see that crowd, man, it’s an experience.”
From three o’clock in the afternoon until 11 o’clock at night, the live music plays practically nonstop, facilitated by an innovation made possible by Playboy: A large center-stage circular platform, bisected by a partition, ensures the continuous soundtrack. As one band plays on the audience-facing side of the platform, the other is a whirl of stagehands and musicians quickly loading out one band and setting up another. When one set ends, it fades into the next as the circle slowly revolves to reveal the upcoming act. It is unlike any other festival in its efficiency.
“We’re blessed to have that turntable,” says Chan. “It’s what makes our festival a little different.” When the Bowl was remodeled, Playboy paid to have the platform installed permanently. The old equipment required workers to rotate the stage manually. “Now I just press a button,” says Chan.
Nearly 60 years after its debut, the festival is still carrying on Hefner’s mission of bringing a lifetime’s worth of music to a single weekend. (This year’s all-star lineup includes Charles Lloyd and Lucinda Williams.) The only thing the listener has to do is remember to bring a corkscrew.
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