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Jazz-age Nights

March 2023
2min read

Night life is one of the most ephemeral aspects of any time. Fashions change, performers pass, clubs and dance halls fade into memory. Two spots offer the Chicago visitor a chance to turn back the clock.

Tommy Gun’s Garage is a dinner theater in a warehouse at 1237 South State Street. The police department once used the place as a target range, but the guns here now shoot only blanks, and a waggish atmosphere is enforced. You need to know the password in order to gain admittance at the back-alley entrance. Waiters and waitresses all dress in period costumes and speak a contagious Damon Runyon patois. They later join in the song and dance onstage, which includes some competent torch singing and brisk comedy routines. A real 1928 Model A Ford sits in one corner, a prop for souvenir photographs.

Hokey? Yes, but Tommy Gun’s does convey something of the fun of the Prohibition era. If the Eighteenth Amendment brought Chicago Capone, it also brought a boisterous anything-goes attitude. The dry forces forgot the lesson of Eden. Citizens loved to tipple on the sly. They shook off the last vestiges of Victorian restraint and kicked up their heels in the Charleston.

Another spot to sample the flavor of those incandescent nights of the Jazz Age is the Green Mill Jazz Club at 4802 North Broadway. This apotheosis of cocktail lounges has a fascinating history in itself, documented in a scrapbook kept behind the bar. Opened in 1907, it was a regular watering hole for Wallace Beery and Broncho Billy Anderson when they were making silent Westerns at the nearby Spoor and Anderson studios.

During the 1920s the Green Mill became a popular nightclub. Headlining in 1927 was the comedian-singer Joe E. Lewis. He would retail the story that the Capone torpedo Jack McGurn owned an interest in the Green Mill and tried to persuade the entertainer to refrain from moving to another club. Others have suggested that Lewis’s problems stemmed from a jealous husband. In any case, a week after Lewis opened at the new bistro three men burst into his apartment, beat him with pistols, and almost severed his talented tongue with knives. It took him years to put his career back together. Later, Capone, a Lewis fan, asked him, “Why the hell didn’t you come to me when you had your trouble?” He offered the comedian a sizable loan.

Another personality associated with the Green Mill was Mary Louise (“Texas”) Guinan, an impresario who operated night spots in New York and Chicago. Her tag, “Hello, sucker,” became a Prohibition catchphrase. The spectacles she mounted featured an abundance of flesh and spangles. A 1930 shooting in the Green Mill led the police to close her show there for good.

Today the Green Mill retains much of its original gaudy elegance. Baroque gilt frames enclose murals; green plush upholstery lines the booths. Most nights jazz combos light up the intimate stage. They remind us that during Prohibition the city became a mecea for musicians. They added a hardswinging elegance to the exuberant ensemble play imported from New Orleans and made the improvised solo a standard feature of arrangements. Louis Armstrong made records in Chicago during the late 1920s, tunes like “Tight Like This” and “Potato Head Blues,” which musicians still listen to with awe.

The jazz masters were intimately involved with the gangsters, who ran most of the clubs and speakeasies where they played. The clarinetist Mezz Mezzrow described them as “blowtops born with ice-cubes for hearts and the appetites of a cannibal.”


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