The relationship between crime and hip-hop runs deep; many rappers are sponsored by criminals, inspired by them, or in rare cases, even lived the life themselves. In the late 1980s and early 1990s, several New York rappers—inspired by the long legacy of films like The Godfather, GoodFellas, and Casino—introduced the world to hip-hop's cinematic equivalent. But it wasn’t just the one-dimensional glory that enamored a generation of hip-hop auteurs—although sometimes it could be that, too. Within these dramatic renderings of mob life, rappers saw the dramatic arcs that reflected the very real dynamics of the street stories that were experienced, observed, or passed on down through the generations.

The Mafia's influence on hip-hop takes on different forms: idealizing the lives of mythic gangsters past and present (Al Capone, John Gotti). Celebrating the many rewards of the fast life, the sudden popularity of suits and wide-brimmed fedoras, or simply emulating the epic scope of the fictionalized, dramatized versions seen in film and on television—the intertwining hip-hop obsessions of realism and flights of kingpin fancy are the absorbing tension at the heart of the Mafioso rap subgenre. Although the peak of the Mafia's influence was largely restricted to New York and the mid-1990s, hip-hop’s embrace of Mafioso tics and tropes was an energizing force, and spawned some of the genre’s best records.

Aside from a few lyrical references to Tony Soprano though, hip-hop’s Mafia obsession is not what it once was. Much as Unforgiven marked the end of America’s obsession with westerns, The Sopranos seems like the place where pop culture’s interest in the Mafia life may have reached its denouement. Yet its influence continues to filter down in unexpected ways. Soon, hip-hop began to produce its own films, telling its own stories on the big screen—like 2002’s Paid in Full, which told the story of Azie Faison, the Harlem drug kingpin—which then in turn impacted hip-hop.

With that said, let’s take a look at some of hip-hop’s most important mob music moments.