While documenting the bloody Liberian civil war, guerrilla filmmaker Booker Sim found himself obsessed with Capone-N-Noreaga’s The War Report, a hip-hop album that drew complex parallels between crime in New York City’s housing projects and third-world geopolitics. “That album was a way to not just have other people look at the ‘hood but to get people in the ‘hood to look at the rest of the world, and start connecting it thematically,” says the 32-year-old Ottawa, ON native.

Drawn to New York in the late ’90s by the promise of a possible feature film project with Prodigy of Mobb Deep, Sim instead emerged more than five years later with a documentary about another legendary Queensbridge rapper–and the actual architect of CNN’s The War Report–Tragedy (a.k.a. Tragedy Khadafi). Shot over the course of two years, Tragedy: The Story of Queensbridge tells the story of the world’s largest housing project–and the home of one of hip-hop’s richest legacies–hrough the troubled life of the seminal but largely unsung MC.

Though not as revered as other QB rappers like Nas, Mobb Deep, or even Craig G, Trag’s life was made for cinema. His hustler father was murdered before he was born and his mother became a crack addict, leading a pre-pubescent Tragedy to fend for himself before being stabbed and thrown in the East River by local gangsters. After hooking up with Marley Marl, he was sent to Rikers Island at 16, just as the Juice Crew was becoming New York’s pre-eminent hip-hop unit. Though he scored a few successes, like his 1990 LP as Intelligent Hoodlum, life-threatening situations and missed opportunities (a dispute with NORE ended his CNN affiliation following The War Report) have been far more typical.

“Tragedy probably knows 50-80 people who have been murdered,” Sim explains. “He lived the whole ’80s thug life that a lot of these other QB artists–who were barely eating cookies then–rap about.”

But telling the elusive rapper’s story proved difficult: Tragedy was busted (while patching things up with NORE in Union Square) and thrown in jail right before filming was set to start. Although Trag appears in jailhouse interviews and a handful of other scenes, Sim was forced to tell the story largely through the eyes of longtime acquaintances like Clarence “Uncle La” Shack (uncle of Mobb Deep’s Havoc) and Poppa Mobb, a QB OG who took in young Tragedy as a son.

While Sim received some flack for not showing Queensbridge in a more positive light, he plans to continue documenting the community via The Legacy, a TV series about the next generation of QB rappers he’s developing with Uncle La and Peter Spirer, director of Beef and Rhyme and Reason.