12 for 12: Rhapsody in Green Mill

Jazz band at the Green Mill
Jazz band at the Green Mill

There is no music as rich, as expressive or as difficult to define as jazz.

It is deeply personal, yet played to be heard and to affect the listener. It has attitude. It is often ostentatious, but just as often, sullen and sentimental.

From ragtime to gypsy, traditional to avant, big band to bebop, it is steeped in as many different traditions as layers of improvisation. Jazz is deeply complex, totally original and altogether timeless.

Image of the sign outside the Green Mill

For nearly 110 years, Chicago has been home to one of the world’s oldest and greatest living shrines to jazz, the Green Mill Cocktail Lounge. Located in Chicago’s historic Uptown neighborhood, it sits between the Aragon Ballroom, the Riviera and long shuttered Uptown Theatre—but stands apart from any other jazz club in the world.

The Green Mill Cocktail Lounge is a classic, where both jazz and Prohibition history know no equal, in Chicago, or anywhere else in the world. Legends such as Billie Holiday, Al Jolson, Von Freeman, Franz Jackson, Wilbur Campbell, and Clifford Jordan have all played its hallowed ground. Here their legacy lives on in the weathered hands of seasoned masters, and new generations of young hip virtuosos leaving their mark on the club’s rich history.

That history runs deep. The Green Mill first opened its doors in 1907 as Pop Morse’s Roadhouse, a bar and beer garden for mourners from the nearby Graceland and Saint Boniface cemeteries. In 1910, the bar was sold to a local real estate developer who renamed it the Green Mill Gardens—in homage to Paris’ famous “Red Mill”, The Moulin Rouge—where it soon become the epicenter for Chicago’s pre-Prohibition entertainment and boozing.

Table with old pictures on it. One is of Jack "Machine Gun" McGurn

During the 20s, it was a celebrated jazz joint where famed musicians walked among famed gangsters. Back then, Jack “Machine Gun” McGurn, a well-known associate of Al Capone, owned the club and kept a table perpetually reserved for his boss. He also kept tunnels under the bar to smuggle in booze or aid escape in the unfortunate event of a raid.

The Green Mill prospered until after World War II, when its hay day legacy faded and fell into ruin. The club quickly went from a nightlife hub to a place where day drinking, drug use and passed-out patrons were the norm. And that might have been that. That might have been the end of the era… if not for Dave Jemilo, a Southside Chicago native, bar owner and jazz fan who purchased the Green Mill in 1986.

For the past 30 years, Dave Jemilo has owned, managed and carefully curated the music at the Green Mill. But how has he managed not only to preserve this classic cocktail lounge and shrine to jazz, but to make its original formula more successful than ever?

In this episode of 12 For 12, Adam heads to Uptown to answer this question and to find out what makes the Green Mill Cocktail Lounge so special (and cause Jack “Machine Gun” McGurn turn in his grave).





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