The recent 20th anniversary of Wu-Tang Clan’s groundbreaking Enter the Wu-Tang (36 Chambers), as well as folks remembering the bugged legacy of Ol’ Dirty Bastard (who died nine years ago), got me to thinking about mid-1990s hip-hop culture and its mythology of keepin’ it real.

While the rap music of that decade varied from the bohemian experimentation of A Tribe Called Quest, The Roots and The Fugees to the pop crossover of MC Hammer and Diddy née Puffy, many of us quickly got caught up in the rawness the almighty Wu-Tang Clan, especially producer/MC RZA’s bleak housing project beats. Not since Sly Stone constructed There’s a Riot Goin’ On fueled by cocaine and PCP had anyone made music sound so much like the aural equivalent of intoxicated derelicts, muddy water and dead rainbows.

“My entire production style and music was my way of releasing brutality,” RZA, sitting in his midtown Manhattan studio, told me in 2006. “All the Wu were street dudes living in the projects. We definitely came in crazy.” Along with contemporaries Mobb Deep and DJ Premier—whose own grimy beats with Gang Starr and Nas laid the foundation of ’90s hardness—RZA and Wu-Tang became connoisseurs of ghetto culture.

There was a sense of danger and blues on Enter the Wu-Tang and its double-album follow-up Wu-Tang Forever, as well as in the coarse voices of rhyme animals Method Man, Raekwon, Ghostface Killah, GZA/Genius and Ol’ Dirty Bastard. Their mean streets music became the perfect soundtrack of a generation of post-crack kids wandering crime-ridden hoods blaring beatboxes. Within the textures of RZA’s grooves, one could feel the conflict and chaos of his community.

Critic Jon Caramanica, in a wonderful Wu-Tang essay from the 2003 anthology Classic Material, noted, “The Wu hailed from Staten Island, the only New York borough that had not yet made a firm footprint on the city’s hip-hop scene. With their debut, they made it sound every bit as foreboding as the locals they were seeking to overtake.” Without a doubt, the Wu contributed to the comeback of a New York sound that had nothing to do with being jiggy. (See, by contrast, Sean “Puffy” Combs and his bad boys swilling flutes of champagne on private planes.)

From the distance of my then Chelsea apartment, Staten Island resembled a macabre movie set straight out of Candyman. Dragging the listener through the heart of horror-show of darkness, “Protect Ya Neck,” “C.R.E.A.M.” and “Da Mystery of Chessboxin’” became broken-glass anthems for a generation. “We took the good things and the bad things [of the ghetto] and put it into a musical form,” RZA continued. “Some people live that same life. For those who haven’t lived that life, it gives them a dose of that life. They can live it through us.”

Seemingly overnight, with the intensity of crack, lots of boys to men started acting like the ghetto was Mecca and Malcolm X had died for their right to sling rock, blast guns and talk about prison as though it were a vacation home. Even I, a then 30-year-old hip-hop critic who went to Catholic school and collected comics, couldn’t get enough of the hard knock life depicted in the Wu’s often-abrasive music.

Once, when my mom overheard me telling a friend that I came from the ghetto, my mother started laughing. “Boy, why you always saying you come from the ghetto? You don’t come from the ghetto. And when I took you to the ghetto, you always acted like you were afraid.”

Certainly, it’s easier to pretend being from the ghetto than to actually have to live through the experience. Everything but the burden, as folks used to say. Yet, as writer Kevin Powell once pointed out in Vibe, “…as we glamorize the ills of ghetto life—the violence, the misguided sexual behavior, the rampant drug and alcohol use—we also box ourselves into a collective corner.”

Enter the Wu-Tang (36 Chambers) was the perfect career launch for all involved, and the one Clansman who got boxed into a corner was the intoxicated prince Russell Jones, a.k.a. Ol’ Dirty Bastard. With his outrageous persona firmly established, he simultaneously became the most interesting and most appalling MC on the pop charts. Released in 1995, Dirty’s solo joint, Return to the 36 Chambers: The Dirty Version featured “Shimmy Shimmy Ya” and “Brooklyn Zoo,” as well as cover art that was a reproduction of his welfare card.

Doing the singing/rapping style years before Ja Rule or 50 Cent, Rolling Stone called ODB “The most original vocalist in hip-hop history,” but away from the mic he was a mess. Be it drugs, a mental unbalance or whatever, Ol’ Dirt Dog just wasn’t right. But just like observing the antics of a wacked-out court jester, the world was always ready to chuckle at his latest antics. Whether Dirty was running from the police or bum-rushing the stage at the 1998 Grammy Awards to declare “Wu-Tang is for the children,” we all simply laughed.

Nevertheless, the truth of the matter was the man was suffering. In 2003, when Ol’ Dirty was released from prison after being there since 2001 for crack possession, I visited him at his mother’s home in Park Slope, Brooklyn. Although Dirty was sober, he seemed to be highly medicated. The Dirty I met was a shell of a man who’d long ago been broken by ghetto foolishness, keepin’ it real ridiculousness and representin’ self-destruction.

Ten years later, I still recall how sad the entire scene made me. Noticing my glance at the gold record for Enter the Wu-Tang hanging on the wall, he looked at me and said, “I don’t even remember making that record. When I was drunk, I was in another world. All I remember was waking up and having a hangover.”

Nearly a year after our interview, ODB passed away on November 13, 2004. Overdosing on a mixture of cocaine and tramadol, he collapsed in RZA’s midtown studio. Two days later, he would’ve been 36.

Cultural critic Michael A. Gonzales has written cover stories for Vibe, Uptown, Essence, XXL, Wax Poetics and elsewhere. He’s also written for New York and The Village Voice. Read him at Blackadelic Pop and follow him on Twitter @gonzomike.