Robert Baird

Hef is gone and whether you think he was a villain, a visionary or a skeezy old fool, the news, alleged by his widow and some recent former girlfriends was shocking: Hefner, who let’s not forget was 91 when he died, had taken so much Viagra that may have experienced a rare side effect and lost his hearing. In other words, he’d chosen sex over music.

You can debate the merits of that trade, but what was weird was that Hefner had always been such a music fan, supporting jazz in particular.

I interviewed for an editorship with Playboy many years ago, and all during the interview which was in the magazine’s headquarters in Chicago, Hefner was maniacally faxing from California, back and forth, over how many cartoons would appear in an upcoming issue. I came away convinced he was micromanaging the magazine in unhealthy ways. But I also knew mostly through my father, who talked about how there was great jazz writing in the magazine (which he only read for the articles of course), that the mag had an abiding interest in music. In the pages of Playboy Hefner relentlessly promoted Hi-Fi gear because it was hip and cool and part of living the good life. Technology in general and cars in particular were one of the magazine’s constant subjects.

And there were other jazz connections as well. The Playboy Jazz Festival, first staged in 1959 in Chicago and reignited in Los Angeles in 1979, continues to this day. In the magazine itself, a 1962 interview with Miles Davis conducted by Alex Haley is justly famous. John F. Goodman’s pieces on Charles Mingus are worth seeking out. The branded TV show Playboy’s Penthouse (1959–61) hosted a number of jazz performances. A later show, Playboy After Dark (1969–70), booked a wide variety of music, everyone from Iron Butterfly to the Sir Douglas Quintet. Members of the Grateful Dead have alleged that when they appeared on a 1969 episode, they dosed the staff, including Hefner, with LSD via coffee but that may be revisionist history. See the awkward, delicious Garcia-meets-Hef moment below.

For a time the famous Playboy clubs with their cotton-tailed waitresses would book live jazz by big-name artists like Dizzy Gillespie. If you’d like to learn more about the connections between Playboy and jazz, Patty Farmer has co-authored a 2015 book with New York jazz writer Will Friedwald called Playboy Swings that discusses it in detail.

The reasons for Hefner’s interest in jazz are not hard to discern. Jazz was thought of as being sophisticated and if nothing else Hefner thought of himself as the ultimate sophisticate tastemaker. To his credit, he was also an early and devoted supporter of the civil rights movement in this country.

Pondering all this on yet another delayed subway train, I remembered the Playboy record label. Once home I began digging for copies of Playboy records, most of which, to my surprise, turned out to be country music albums and singles by the likes of Mickey Gilley (owner of the famous Houston nightclub featured in the film, Urban Cowboy), Hef’s girlfriend at the time Barbi Benton, and pioneer of the Bakersfield sound, the great Wynn Stewart. Upon further exploration, the label also released records by songwriter Jimmy Webb, R&B singer Major Lance and even did a Leadbelly reissue. Probably their biggest hit was 1975’s “Fallin’ in Love,” which was the title of a single and an album by Hamilton, Joe Frank & Reynolds.

The original label was closed in 1978 but a new label, Playboy Jazz, which finally focused on Hefner’s original musical interest, was launched in alliance with Concord Records in 2001. To date, Playboy Jazz has only released six compilations drawn from the Fantasy Records catalog (Prestige, Riverside, Milestone, etc), which Concord now owns. The titles all play on the “After Dark” theme of the second TV show. The latest Jazz Love Songs After Dark is a mix of old and new tracks from Bill Evans, Joe Williams and Miles Davis.

Grateful Dead on "Playboy After Dark" * 1969 from moontroll on Vimeo.