Throughout its uproarious history, The Green Mill Jazz Club has played host to a number of famous - and often infamous - celebrities. Opened in 1907 as Pop Morse's Roadhouse, the "Mill" was a stopping place for mourners to celebrate the passing of a friend before proceeding to St. Boniface's Cemetery. By 1910, new owners had converted the roadhouse into the Green Mill Gardens, complete with lantern-lit outdoor dancing and drinking areas, and boasting such headliners as Al Jolson, Eddie Cantor and Sophie Tucker. Actors Wallace Beery and Bronco Billy Anderson also visited the Gardens, hitching their horses to the outdoor post and settling down for a drink after a days work filming westerns at nearby Spoor and Anderson Studios.
As the twenties roared, The Green Mill became mobster territory when Al Capone's henchman, "Machinegun" Jack McGurn, gained a 25% ownership of the club. Manager Danny Cohen had given McGurn the 25% stake to "persuade" comedian/singer Joe E. Lewis from moving his act south to the New Rendezvous Café at Clark and Diversey. McGurn managed to convince Lewis by slitting his throat and cutting off his tongue. Miraculously, Lewis recovered, but his songs never regained their lush sound. The incident was later immortalized in the movie The Joker is Wild, with Frank Sinatra as Joe E. Lewis and a Hollywood soundstage as The Green Mill. Of course, his interest piqued, Sinatra had to visit the club.
Throughout the 1930s, '40s, and 50s, The Green Mill continued to pack 'em in with a heady mix of swing, dance and jazz music. Uptown crowds from the Aragon Ballroom or Uptown and Riviera Theaters would "stop in for one" before or after shows. Business began to slip in the mid-seventies, and in 1986, present owner Dave Jemilo bought The Green Mill and restored it to its prohibition-era, speakeasy décor.