[Editor's note: Weekly scribe Jeff Weiss's column, “Bizarre Ride,” appears on West Coast Sound every Wednesday. His archives are available here.]

Before he transformed into “Hef,” the pajama-clad and priapic founder of Playboy, Hugh Hefner was a jazz crooner billed as “the boy with the bop in his voice.” The nickname dates back to his undergraduate days at the University of Illinois, when the “Campus Ballad King” prophetically covered songs like “My Desire.”

That was 65 years ago, but Hefner's love affair with music has never waned. Celebrating its 35th anniversary at the Hollywood Bowl this weekend, the Playboy Jazz Festival exists as immutable testament to the Playboy potentate's earliest obsession growing up in Chicago.

“Jazz was everywhere back then. I was born in 1926, and in the 1930s jazz was the predominant music of pop culture and romance,” Hefner says, taking a phone call at “the mansion,” his Gothic-Tudor Xanadu. He's hard of hearing in his right ear but otherwise sharp and willing to reminisce.

By the time Playboy started in the 1950s, rock & roll had become the predominant soundtrack of white youth. But from its inception, the magazine embraced the African-American art form then flourishing on the South Side of Chicago, where Hefner lived during the early years of the Eisenhower era. Playboy's first issue included an interview between Alex Haley and Miles Davis.

“One of the reasons why I loved seeing live jazz on the South Side of Chicago was that they were among the only racially mixed venues in the city at the time,” Hefner remembers. “When we opened the Playboy Clubs, I took pride in helping to further integrate the nightlife scene.”

Hefner self-identifies as a jazz purist. His all-time favorite player remains Bix Beiderbecke, the cornetist and jazz pianist who died under murky circumstances in 1931. He cites Louis Armstrong, Count Basie, Glenn Miller, Duke Ellington and Benny Goodman as other heroes. Many of these artists, now long dead, are alumni of the Playboy Jazz Festival.

“I love the jazz in its earliest forms. It's the one pure American art form. It comes from the roots of this country,” Hefner says. “I have strong nostalgic connections with it. It will always represent youth and rebellion to me.”

Hip-hop long ago eclipsed jazz as the rebel music of black youth. But as I mentioned in last week's column, the form is having a rebirth, thanks to L.A. iconoclasts Flying Lotus and Thundercat. Hefner is no big fan of rap but points out the obvious links binding the two. And, of course, he notes the nexus between jazz music and carnal desire.

See also: A Jazz Renaissance Is Happening In Los Angeles

“One has to understand there is a connection between jazz and sex,” Hefner says. “Jazz emerged from the New Orleans red-light district. The original spelling of the word was 'jass' and it meant sex. It was less than respectable, which only added to the appeal for a young person.”

The ardor for jazz reflects a more fleshed-out portrait of Hefner than the silk-robed lothario of popular cliché. Since the inception of Playboy, he's been a staunch advocate for gay rights and civil rights and a foe of drug prohibition. He is a libertine but a liberal-minded one, an aesthete who was very progressive in contrast to most of his peers. His inaugural Playboy editor's letter highlighted his love of “putting a little mood music on the phonograph and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz [and] sex.”

At 87 years old, he's obviously attuned to how he will be remembered, which in his opinion encompasses sound, as well as sex.

“I would hope my championing of jazz will be remembered in a connective way with what's unique about Playboy and my own legacy,” Hefner says. “As a musical form, jazz represents the same liberation and freedom that America represents in its most ideal form.”

Follow us on Twitter @LAWeeklyMusic, and like us at LAWeeklyMusic.

Austin Peralta Died From Pneumonia Combined with Drugs and Alcohol Says Coroner

Top Ten Jazz Albums for People Who Don't Know Shit About Jazz

Five Historic L.A Jazz Spots

Top 20 Musicians of All Time, in Any Genre

Advertising disclosure: We may receive compensation for some of the links in our stories. Thank you for supporting LA Weekly and our advertisers.

LA Weekly