“I’m the first generation hip-hop filmmaker,” late director extraordinaire John Singleton proudly proclaimed in George Alexander’s 2003 volume Why We Make Mov!es: Black Filmmakers Talk the Magic of Cinemas. “I was 11 years old when 'Rapper’s Delight' came out, so I’ve grown up with hip-hop. If you look at all of my movies, they’re hip-hop films, because they have a different sensibility than the films from the filmmakers who came before me, like Melvin Van Peebles, Gordon Parks, Michael Schultz, Spike [Lee] and Eddie Murphy.”

Singleton, who tragically passed away at the untimely age of 51 this week after suffering a stroke, was not at all engaging in chest-beating hyperbole. The acclaimed African-American Oscar nominated auteur, of the 1991 landmark Boyz N the Hood, brazenly crashed Hollywood’s lily-white, exclusive party with his powerful, cautionary examination of urban life in one of the nation’s most infamous areas of South Central, LA, where Singleton grew up.

The ambitious USC film student-turned-cinematic agent for change came of age during the volatile ‘80s, an era when the crack epidemic, police brutality, racism and Ronald Reagan’s economics were doing a number on poor, Black communities nationwide. Like most teenagers then, Singleton was an obsessed hip-hop head.

In various interviews, he credited celebrated political rap heroes Public Enemy’s 1988 masterpiece, It Takes a Nation of Millions to Hold Us Back, with changing his life. When he spoke at a New Music Seminar panel discussion in 1991, billed as Hip-Hop as an Art, a Style and a Culture, he said of the street-birthed genre:

“The music reflects the condition of the culture. Film is an extension of the music. A lot of these people doing so-called hip-hop films just do it about the culture. They think if they put the word homeboy in there 25 times, it’s a cool film. In Boyz N the Hood, nobody’s rapping, but it’s a hip-hop film because it has the political as well as the cultural aesthetic that rings true.”

It’s true. Not only did Singleton name Boyz N the Hood after Eazy-E and N.W.A.’s 1988 wildly profane, straight-no-chaser debut single, he had the vision to recruit former N****az With Attitude standout member-turned-solo hell-raiser (and now-movie powerhouse) Ice Cube, for a pivotal role in his make-or-break film despite having no experience. Criminally underrated rapper YoYo also makes an appearance as an around-the-way girl.

Yes, Melvin’s son Mario Van Peebles, who inherited the film making gene from his pioneering pops, was the first director to cast an MC in a mainstream film strictly as an actor (Run-D.M.C. and Kid ‘n Play rapped in their previous films) when he tapped OG West Coast rhymer Ice-T for his 1991 Harlem gangster drama, New Jack City. But Singleton was the first filmmaker to truly understand the power of hip-hop — stylistically, musically and culturally. Besides, could you ever imagine the man doing anything as remotely cheesy as this?

Never mind the industry joke that Singleton’s casting couch was inside a recording studio, he was already friends with the mercurial Tupac Shakur before the release of the rapper’s startling film breakthrough in Juice, appearing in 2Pac’s early video for his 1991 single “If My Homie Calls.” When Singleton offered ‘Pac a co-starring role alongside global pop behemoth Janet Jackson for his romance drama Poetic Justice (1993), he wasn’t clout chasing — Singleton lived and breathed the culture on every level.   

No one would ever confuse the stoically dressed Singleton as an on-the-go stylist, yet he was the one to convince Jackson to wear box braids in Poetic Justice, a hairstyle that was both unapologetically Black and hip-hop. Singleton also understood the galvanizing impact rap music could have on the big screen as exemplified on the gold-selling Boyz N the Hood soundtrack. (He had the good taste to feature Ice Cube, Compton’s Most Wanted and Main Source on the same album.)

Singleton established a record label division in his company New Deal Productions, and had every intention of signing underground, up-and-coming rapper-producer Warren G, who, despite contributing samples to Dr. Dre’s smoked out The Chronic (1992) and appearing on Snoop Dogg’s sonically brilliant Doggystyle (1993), was left out of the Death Row fold by infamous mogul Suge Knight.     

Good thing Singleton saw something in Warren’s laid back G-Funk. According to Greg Geitzenauer, who would go on to engineer Warren G’s multi-platinum single, “Regulate,” the director recognized the kid’s vision before anyone else.

“It was at this time that Warren had some money to do a demo. He said, ‘Hey, I’m going to do this thing for this John Singleton movie as a producer with this guy Grimm, do you want to engineer it?’” Geitzenauer explained to BET of a recording session that was capped by Mista Grimm’s “Indo Smoke,” an addictive ode to weed featuring the rumbling studio chops of Warren G and the late hook maestro Nate Dogg that eventually became a favorite Poetic Justice cut. “That did well, and soon Def Jam gave Warren some advance money to start recording some stuff as well.”

Singleton was relentless, and there would be even more hip-hop castings: A reunion with Ice Cube in 1995’s Higher Learning; the animated Busta Rhymes in 2000’s Shaft; Snoop Dogg in 2001’s Baby Boy; Ludacris in 2003’s 2 Fast 2 Furious; and OutKast’s Andre 3000 in 2005’s Four Brothers.

When no one in Hollywood would finance his polarizing Memphis rap underdog drama, Hustle & Flow (2005), he put up his own money to finish the film before sparking a bidding war that would balloon to $9 million.

Lead star Terrence Howard ultimately earned an Oscar nomination in the category of Best Actor, and Southern rap giants Three 6 Mafia took home the award for Best Original Song, their controversial “It’s Hard Out Here for a Pimp.” In the end, Singleton had the last laugh.

How hip-hop is that?