When a famous crooner performs for the Chicago Outfit, being a good singer means something different.
During the 1950s and 1960s, the Armory Lounge at 7427 W. Roosevelt Road in Forest Park, Illinois, was much more than an ordinary neighborhood watering hole. Chicago Outfit boss Sam “Momo” Giancana and his associates regularly gathered there and conducted business from the restaurant’s booths.
Despite its unassuming appearance, the Armory attracted some remarkably famous visitors. Frank Sinatra and Dean Martin were among the entertainers associated with the establishment, and Forest Park Mayor William Meyer reportedly hosted a dinner for the two singers there in 1958.
But another celebrated voice also has a connection to this unlikely mob hangout: Vic Damone.
Known for his smooth baritone and hits such as On the Street Where You Live, Damone was a major star of American popular music. His career took him to prestigious nightclubs and concert venues, making his reported appearance at the modest Armory Lounge particularly unusual.
In an episode of the Gangland Wire podcast, retired Kansas City police intelligence detective Gary Jenkins recounts that Damone brought his act to Giancana’s Forest Park establishment. Jenkins highlights the contrast between Damone’s celebrity status and the neighborhood setting.
The precise date and circumstances of the performance remain unconfirmed, but the account illustrates the remarkable intersection of entertainment and organized crime in mid-century Chicago.
In mob circles, however, the word “singing” could mean something entirely different. A singer might entertain an audience, but a “canary” who sang to federal investigators could find himself considerably less popular.
Fortunately for our fictionalized Vic Damone, he seems to know which audience to sing to.
