Since its inception in 1959, when it was billed as “The Greatest Three Days In The History Of Jazz,” the Playboy Jazz Festival has made history. Then, it was the first indoor jazz festival in American history. The event drew more than 70,000 fans to Chicago Stadium for five shows over three days between August 7th and 9th.

The first festival included such luminaries as Dizzy Gillespie, Dave Brubeck, Ella Fitzgerald, Kai Winding, Miles Davis, Count Basie, Jimmy Giuffre, Oscar Peterson, Louis Armstrong, Duke Ellington and Sonny Rollins. Back then, the Catholic Church attempted to block the festival largely because of its association with Playboy.

Though the event was a rollicking success, it would be 20 years before another took place. When it returned in 1979, it was to the Hollywood Bowl, where it’s been held ever since. We’re just days away from the 39th annual Playboy Jazz Festival, so let’s look back on some iconic performances.


SHEILA E, 2012
Sheila E’s performance in 2012 brought samba front and center. She was joined by a series of dancers in iconic Brazillian garb and delivered a performance attendees wouldn’t soon forget. Take a front row seat as she brings her signature blend of samba and funk to Playboy.


ETTA JAMES, 2007
Etta James is one of the best singers ever. So it makes sense that we should include her powerhouse performance of “At Last” at the 2007 Jazz Festival. She commands the crowd with little but her voice. The song gains even more immediacy live, as she’s one of the rare performers whose vocal range isn’t diminished when she steps out the studio. A true legend.


THE GREAT QUARTET, 1982
McCoy Tyner, Freddie Hubbard, Ron Carter, Elvin Jones more than lived up to the name they gave themselves. This performance from The Great Quartet is electrifying. Perhaps more electrifying is the ‘80s fashion on display in the audience. This performance makes one of the best cases for live jazz; it’s electrifying, vital and the performers play in perfect sync with one another. The level of performance and synchronicity here is outstanding.


MAYNARD FERGUSON, 1982
If leading a band were a sport, Maynard Ferguson would be in the Hall of Fame. In fact, he was inducted into the Down Beat Jazz Hall of Fame in 1992. Here, he performs both as the leader and as a performer. You can see why his trumpeting was considering almost unmatched; the instrument seems to nearly sing when he enters the mix. Even more legendary than his trumpeting was his white jacket-sunglasses combo. A daring move at night, but Playboy has always been about taking risks.


MILES DAVIS, 1959
You actually can’t get better than Miles Davis. It’s impossible. People have died in the attempt. One guy had his lips literally explode when he was trying to blow like Miles. It’s true, there’s a hospital report and everything.* He’s at his absolute peak here, in a performance of “So What” from the first Playboy Jazz Festival.

*This is absolutely not true.

But tickets to the 2017 Playboy Jazz Festival here.