Hugh Hefner may have had dozens of girlfriends over his 83 years, but his life-long love is jazz. Hefner declared his undying devotion to swing and big band music when the Rabbit interviewed him in 2008 for an inside story, “Jazz Playboy Style.” With all the recent attention, good and bad, given to Hefner –  Brigitte Berman’s documentary ” Hugh Hefner: Playboy, Activist and Rebel that premiered at this year’s Toronto Film Festival, a  forth coming Hollywood biopic to be directed by Brent Ratner, a feature in the New York Times, rumors of financial problems and bad mouthings from former girlfriends — the Rabbit feels its time to revisit Hefner’s jazz legacy. Everyone knows what he did for the middle-class male libido. Let’s not overlook what he’s done for music.

“My own taste in music, as is often the case, was defined by my early experiences,“ he said in an afternoon call from the mansion. “There were two major sources of music in those days, the big band broadcasts on radio and recordings. I had some occasion in high school to take a girlfriend to a ballroom or a theater and see a band. I saw the Tommy Dorsey Orchestra, the Harry James Orchestra, a couple of my favorites at the time. I really love the early origins of the music, the Dixieland, blues, and New Orleans music of the ‘20s and ‘30s. One of my favorites is Bix Beiderbecke. We still play a lot of him around here.”

Playboy’s affair with jazz dates to its very first issue in 1953 that included, along with the famous pictorial of “sweetheart of the month” Marilyn Monroe, a profile of the Dorsey Brothers. The magazine introduced its jazz poll in 1957 and its very first interview subject was Miles Davis back in 1962. The panel discussion on the state of jazz in Playboy’s “Jazz and Hi-Fi” issue of February 1964 included the likes of Dizzy Gillespie, Dave Brubeck, Gerry Mulligan, Cannonball Adderley, Charles Mingus and Stan Kenton among others. The discussion center on the future of jazz, how it might evolve, where it would be performed and how it would attract new fans. The schisms between old and new, tradition and innovation and even black and white are often visible. Still, the comments somehow seem apt all these years later.

Hefner often brought jazz standouts to his television series Playboy After Dark and Playboy’s Penthouse, appearances that demonstrated his love and knowledge of the music. In a classic scene from a 1959 installment of Playboy’s Penthouse, Hefner introduces the “divine” Sarah Vaugh with the respect and affection of a dedicated jazz fan. He notes that she’s appearing at The Empire Room in NewYork’s Waldorf Astoria Hotel, a club not normally associated with jazz. “That’s quite a transition,” Hefner says. The singer agrees, saying she’s trying to attract those listeners as well. Hefner talks of Sarah’s early involvement with Earl Hines pre-bop band that included Dizzy Gillespie and Charlie Parker. He lets Vaughn introduce her accompanists. Then he steps back to let her enchant us with “Broken Hearted Melody.”

Or take another example from a 1960 broadcast . Count Basie is at the piano at what appears to be a swank penthouse party (it was actually a studio at Chicago television station WPKB ). Occasionally playing with one hand while cradling a cigarette in the other, Basie accompanies singers Dave Lambert, Jon Hendricks and Annie Ross, joined by Basie’s ”favorite son,” singer Joe Williams. They scat along to “The King,” a tune from the Lambert, Hendricks and Ross LP Sing A Song Of Basie. The composition pays homage to jazz royalty:  “Earl “Fatha” Hines, Duke Ellington and, of course, the Count. As the singers improvise a spiraling series of scat lines, a tuxedo-clad Hefner and a host of impeccably dressed men and women bounce along to the irresistible beat. Television has seldom seen a hipper moment.

The magazine, like the culture at large,  has largely ignored jazz over the last several years. And Playboy’s signature jazz festival, held annually at the Hollywood Bowl, has become something other than a celebration of jazz (though it always pays homage). But to find Hefner’s true devotion to the music of his youth, travel back to the inaugural Playboy Jazz Festival, staged at the old Chicago Stadium in 1959, an event that included a long list of the top jazz names then on the planet.

“What made Chicago [Playboy Fest] unique for me was the time frame and the giants that were there. [Jazz critic] Leonard Feather called it the single greatest weekend in the history of jazz. I wasn’t that far from my college and high school years and there I was standing on stage with all the greats that influenced me and were celebrities to me. It’s a moment impossible to recapture.”–Cabbage Rabbit

Mark Harris’ account of the making of the five “Best Picture” nominees from 1967 is an epic tale of art, business and character. The films represent old Hollywood’s formulaic approach and devotion to past success (Doctor Dolittle), it’s frustrations in attempts at relevance (Guess Who’s Coming To Dinner), the obstacles it faced in coming up with something truly innovative (Bonnie and Clyde, The Graduate) and its successes it spite of itself (In the Heat of the Night). Slow to respond to the desires of its audiences and resistant to new ideas and faces, Hollywood of the 1960s is portrayed as a giant dragged screaming into the future (has anything changed?). Richard Fleischer, Stanley Kramer and other established, mainstream directors give ground to progressives Arthur Penn and Norman Jewison and others weaned on the French New Wave while upstart theater director Mike Nichols challenges them all. Harris’ narrative is masterfully woven from subject and theme as well as the colorful threads of the various principals. The book can be enjoyed simply for it personalities: a persistent yet insecure Warren Beatty, the fearful, self-conscious and beautiful Faye Dunaway, Rex Harrison’s drunken self-obsession, the perseverance of Dustin Hoffman, Sidney Poitier’s dilemma as the only major black film star, Katherine Hepburn’s mothering of Spencer Tracy, Tracy’s alcoholism and physical decline. Its backdrop is the uneasy alliance between creativity and commerce, America’s racial struggles and a society ready to change and not sure how to go about it. Part cultural study, part juicy gossip, Pictures is a must for those interested in the past and future of cinema. And aren’t we all?—Cabbage Rabbit