The Crooning Underworld: How the Mob Shaped Post-War American Pop Music

In the post-World War II era, before the glitz of “The Voice” and “America’s Got Talent,” aspiring pop singers often found their initial break on radio shows like “Arthur Godfrey’s Talent Scouts.” Success on such programs could lead to club bookings and, eventually, recording contracts. For handsome young baritones like Vito Farinola, a name change to something more upbeat, such as “Vic Damone,” was common. This was part of the “Americanization” process, a trend amplified by the rise of popular Italian-American singers like Sinatra, Bennett, Dean Martin, and Perry Como, who infused pop music with a distinct Neapolitan flavor. Damone’s early hits at Mercury Records in the late 1940s, including “I Have But One Heart” and “You’re Breaking My Heart,” were English-lyric adaptations of Italian songs his immigrant father used to play, suggesting a smooth path ahead.

However, Southern Italy’s influence on the post-war music industry extended beyond musical style. Once established on the pop charts, singers like Damone moved to larger, more prestigious venues such as New York’s Copacabana, Las Vegas’s Flamingo, and Miami Beach’s Beachcomber. These were “classy” establishments with undeniable ownership. “If you were an entertainer in those days, you automatically performed at Mob-owned places,” Damone recounted in his autobiography. “There weren’t that many other clubs for you to go to.” This proximity to the Mob came with significant expectations and implicit dangers. Damone himself faced a terrifying ordeal when he broke off an engagement to a mobster’s daughter. The enraged father, upon learning of Damone’s refusal to accept his daughter’s disinterest in his mother’s manicotti recipe, dangled the young singer headfirst out of a 14th-floor window. His life was spared only when Frank Costello, a prominent figure in the New York Mob, intervened with a decisive “thumbs-up” at a meeting convened to resolve the dispute.

The entanglement with organized crime persisted. More than a decade later, Robert Kennedy approached Damone at Peter Lawford’s residence seeking information about his former fiancée’s father. The singer, bound by loyalty and fear, offered nothing. The pervasiveness of these connections was further highlighted when Frank Sinatra, at the zenith of his career, referred Damone to Sam Giancana for business advice when asked for guidance. “Vic, talk to Sam.” This interconnectedness underscores the deep and often dangerous ties between the entertainment world and the criminal underworld during that era.

Anthony Giardina is a writer whose most recent play, “Dan Cody’s Yacht,” premiered at the Manhattan Theater Club last spring.