Find Chicago’s bleeding hearts at Tommy Gun’s Garage

Find Chicago’s bleeding hearts at Tommy Gun’s Garage


Feb. 18, 2011

At Tommy Gun’s Garage, Valentine’s Day isn’t for the faint of heart. But on Tuesday night, the longtime “speakeasy” in Chicago’s Far South Loop was certainly good for a laugh.

Or, you know, 30.

This week, while countless other couples throughout Chicagoland were dining by candlelight, my girlfriend and I instead chose to spend our Valentine’s Day evening in a different setting.

We enjoyed dinner lit by gunfire.

But, believe me, there was also plenty of romance – that of Chicago’s 1920s-era variety – at Tommy Gun’s, the city’s longest-running audience interactive dinner show which this year celebrates its 25th anniversary.

Located at 2114 S. Wabash Ave. in a nondescript brick building that even Elliot Ness would pass by, Tommy Gun’s was founded in 1987, but the joint exists in the Roaring Twenties. Upon entering – after you’ve given “Gloves” the doorman the password – visitors are instantly transported back to the age of Prohibition, when mobsters and molls ruled the Windy City.

Inside the venue, you’ll encounter wisecracking wiseguys with names such as “Buggsy,” “Knuckles” and “Rocco” and smart-aleck flappers like “Kitty” and “Roxy,” who not only take your dinner orders, but also leap up on stage to sing and dance and all that jazz.

The lively two-hour show ($65 per person) is hosted by Tommy Gun’s maître d’ “Vito Calamari,” who carries around a wooden baseball bat and, if you happen get up to use the restroom, is liable to steal your seat and try to steal your date.

Twice, in my case.

Each year on Valentine’s Day, Tommy Gun’s adds a macabre twist to its standard song and dance by ending its show with a re-enactment of the infamous “St. Valentine’s Day Massacre,” which took place on Chicago’s North Side on Feb. 14, 1929.

Back then, Al Capone’s gang was at war with George “Bugs” Moran for control of the city’s bootlegging market. Not long before Valentine’s Day, Moran and one of his henchmen had murdered a Capone associate, prompting Capone to decide that enough was enough.

In an attempt to eliminate Moran, Capone arranged to have him informed that a special shipment of bootleg whiskey would be shipped to a garage at 2122 N. Clark St. owned by Moran. When seven of Moran’s associates arrived at the location, four of Capone’s men stormed in posing as police officers conducting a raid.

The “cops” lined Moran’s men against a wall, pulled machine guns out from beneath their overcoats and opened fire. Moran was not present and survived. Capone, meanwhile, was in Florida and police were unable to link him to the crime. In fact, no one was ever tried in the killings.

The garage where the massacre took place, known as “SMC Cartage Company,” was torn down in 1967. Today, the lot is occupied by a Chicago Housing Authority development for seniors, although the bricks from the wall against which the victims were lined up has gone on an odd post-demolition journey.

Canadian businessman George Patey first bought the wall’s bricks at an auction and then reassembled them in the men’s room of his Banjo Palace nightclub in Vancouver. Reportedly, the bricks became a urinal wall that featured, um, conveniently placed targets.

In 1976, the Banjo Palace closed and the wall was again put up for auction, one brick at a time. Today, some of those bricks have been reassembled inside the new Mob Museum in Las Vegas, which happens to have celebrated its grand opening this week.

On Valentine’s Day.

For more information, visit or call 733-RAT-A-TAT. The theater includes a parking lot and is located near Lake Shore Drive and the Stevenson Expressway (I-55).