Photo via HBO

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Walker Armstrong likes his pit beef with extra horseradish.

Born Michael Kenneth Williams in Flatbush, New York, the man who played one of Barack Obama’s favorite characters was as much a part of the fabric of culture, as he was the communities he portrayed. He died in early September of a drug overdose, but not before leaving an imprint on popular culture that has left many of his contemporaries—and predecessors for that matter—nervously tending their achievements, gawking at his legacy of powerful, boundless acting. Many actors play roles that leave an impression, however, few play roles that mean something greater than their immediate effect. And Michael K. Williams did just that on The Wire.

Early on in his career, however, Williams managed to find work as a backup dancer for such notable performers as Madonna and George Michael, eventually breaking into acting alongside names like Tupac Shakur, as well as the distinguished acting troupe the National Black Theatre Company. Despite a burgeoning career, Williams’ whole life trajectory would change one tumultuous night at a party in Queens.

It was his 25th birthday. He stepped out of the joint to “get some air,” he told NPR, when he saw that some of his friends were about to get jumped by another group of guys. Noticing the tense situation, Williams attempted to diffuse anxieties when someone snuck up from behind.

“The dude wiped his hand across his mouth and smacked me,” he said. “What he did was he spit a razor. He was positioning the razor in his mouth to get it between his middle finger and ring finger. And then he swiped me down my face.”

His mug would be marked by that permanent, defined scar—top of forehead to center-left cheek—and he would nearly lose his life from another blow that just barely missed his carotid. Born out of this welter of something we might have expected to see in an episode of the television show he would become so famous for: the face of the man we’ve all grown to love. Where the sawed-off 12 gauge and austere duster were mere props of the story he so brilliantly told, that scar was the imprint of a reality he braved his entire life. A life of heartache, struggle, lofty heights, and profound talent.


“…that boy was beautiful.”

We all know that Williams played other roles besides Omar Little. Throughout the landscape of film and television, he was known as portraying a range of dynamic and formidable figures. For example, his role as Chalky White on HBO’s slow-burning, Boardwalk Empire, beautifully displayed his range. Unlike other Williams characters, Chalky White takes up the role as a politically savvy and uncompromising leader of the Black community—albeit a crafty bootlegger. Aside from other notable performances in films such as 12 Years a Slave, When They See Us, the 2015 Bessie Smith biopic Bessie, as well as a brief but appropriately humorous cameo in Dan Harmon’s irreverent TV show Community, Williams never truly enjoyed the prolificacy that perhaps he deserved as a masterful actor. However, what he did manage in his extensive career was as great a contribution to culture as any number of successful artists or actors. And it’s no contest that Williams’ greatest contribution was his role as The Wire’s infamously brutal, ineffably complex and cunning Westside stickup kid Omar Little.

Known by everyone in Baltimore as simply Omar, Williams’ portrayal of the proverbial port city Robin Hood, perceived by some as being a vicious and “predatory motherfucker,” was nevertheless an artful illustration of the dialectic of the thug with a heart—the mad villain with a golden soul. The 12-gauge-wielding Omar, renowned and feared throughout the ramshackle streets of Baltimore, is shown to the audience as a loving, loyal man with an affinity for transgressing more than just the normative rules of the street. That is to say, the fearless gun-slinger, Omar Little, is a homosexual. And this detail isn’t sidelined as some speculative character analysis, but rather, his sexuality is a feature of particular import. Omar’s whole character arc in the series, the focal point that sends him on an explosive, and ultimately self-destructive tirade of violence and murder, is centered around him seeking revenge for the torture and killing of his partner, Brandon, at the hands of the Westside drug kingpin, Avon Barksdale.

Although Brandon is described by Omar as “beautiful,” not to mention that some of the fondest moments we see of Omar occur between him and “the boy,” we only see Brandon for a brief stint at the beginning of season one. After he and Omar rob a Barksdale stash house, Brandon, as I mentioned, is captured, tortured, and killed—seemingly, alongside Omar’s only sense of belonging in this world. The subsequent seasons consist of Omar’s Barksdale blood lust, and the vitriolic hatred for anyone who gets in his way. This rage-fueled mania, verging on a kind of neurotic dysphoria, is in many ways the singular, defining characteristic of Omar—the reason Tosha Mitchell was killed, the reason his boyfriend Dante is tortured by “Brother” Mouzone, and, arguably, the reason he was ultimately smoked in that liquor store. But the manner and context Omar is presented to us renders him an incomplete figure in our minds. We will never really be able to explain Omar because he defies any one stereotype. He isn’t just a stickup boy, like how he isn’t just a gay Black man living in the hood; he isn’t just violent, like how he isn’t just loving…

Whether or not we see Omar as a needlessly violent thug bent on revenge, getting high on heisting drugs off hoppers from East to West side Baltimore, or as a devious ghetto Robin Hood substituting the Sherwood Forest for some derelict Edmondson vacant, we can agree on one thing: Omar has had a significant impact on our cultural Imagination. The Wire is one of the best television shows in history—what with the screenwriting genius of David Simon and Ed Burns, the Baltimore street cognoscenti of metro desk and police precinct knowledge, and an acting cast that was as elite as they were relatively unknown, The Wire is unmatched in our ecology of soap dramas and kitschy box-office hype. And of all the firecracker lines and subtle realism dynamic, with all the incredible actors and the characters they developed, Omar stands out like a kind of dead star—despite being revered by cinema heads the world over—a radical light whose glory is only noticed long after its death.

“…you need a lot of context to seriously examine anything.”

Although The Wire is rated the number one HBO show of all time—sometimes coming in a close second to The Sopranos—hardly anyone seems to have heard of it (off Twitter). For example, I was in a class of about 30 or so students recently, and when I mentioned that my favorite TV show was The Wire, no one pricked up their ears or murmured self-assuredly like they had done with practically every other show named. And even when I mention The Wire to most adults, too, I am met with a disappointing mixture of strained Oh yeah’s and confused The-what?’s. Moreover, it seems that more and more, The Wire is becoming one of those cherished cultural delights whose immediate effect burns bright only to wane into a delicate artifact, entombed in classical virtue, later placed on display in museums and in liberal arts curriculum syllabi like so many works of Keats or a masterpiece by Vermeer.

Such comparisons, while melodramatic in tone, are sober given that The Wire is as great an analysis of material conditions and social relations as any number of economics grad students or tenured sociology professors. That is, while some political science postdoc was needlessly dragging herself through the academic muck of MIT, The Wire was conducting political, economic, educational, and social scholarship on a level that was as accessible as it was real, a feat that our (sort of) fictitious political scientist could only dream of.

The Wire is a story about the American city as told through the lens of the war on drugs. No doubt, it is set in Baltimore, MD. However, its subject matter and the story it tells references the woes, miscarriages, and sordid beauty of cities all across the country. As mentioned earlier, David Simon and Ed Burns, the writers of the show, both served in positions that had a unique proximity to the events in The Wire. Simon, with his 15-years experience as a beat reporter for The Baltimore Sun, had a special insight into the inner machinery and cognition of city politics, crime, worker’s unions, and the education system. Burns shared an equal hand in these structural properties of the urban rhizome due to his tenure as a Baltimore Homicide detective-turned-inner-city middle school teacher. The resulting effort more or less, defined a cross-section of the American city, as well as offered insight into the ineffectiveness of the various apparatuses—law enforcement, politics, economics, and education—tasked with solving the problem.

“A man’s gotta have a code…”

From where the audience sits, it would seem that Omar is a rough, disruptive force, not so far removed from the fatalism of The Joker. But that would be a poor reading, and not at all what the writers had in mind, nor is it what appears on screen.

Omar still plays by the rules, just not the rules of the hoppers and police. He kills when he deems necessary, and shows mercy when others might deem it foolish. He works with the police when he feels “someone got to fall,” and he runs with murderers and thieves as long as they see eye-to-eye with his way of doing things. Other characters can’t game this way. They are caught in their moral matrix, they don’t have the luxury of creating one for themselves. And whenever one of those characters tries to rebel against the corrupt or inefficient status quo and carve out an ethical system to fit their evolving perceptions, they are done away with—take Frank from season 2, or Bodie at the end of season 4. Granted, there are some instances where this rebellion yields positive results, such as Poot getting out of the game and Carver becoming a force of “good police work,” as McNulty would say; but even then, Poot works at Foot Locker and Carver isn’t much more than a sergeant doing some good work at the level he’s allowed access to within his much broader context.

Omar is different. To him, the only guiding force is a code that he lives by. A moral structure that’s as simple as it is universal. “No mistakes, no bystanders, no tax payers getting caught up in the mix,” he says in season 1. By applying this Occam’s razor-like methodology, Omar is effectively able to subvert the normative parameters and rules of the street as well as the law. He kills drug dealers and other “criminals.” He robs only those in the game. He snitches only giving up so much information, mostly lying, to seek justice for his slain boyfriend. Such a transgression of the institutions that The Wire examines calls into question every other system and character that Omar touches, reducing what we think we know about how the game works, how the law works, into a pasty and uneasy opacity.

Omar begs the questions that we almost thought too obvious, and frames them in a way that makes life appear even more absurd than when we started. If dealing drugs is a means to sustain life, then what’s the morality of killing and stealing for a product that you did not purchase? If these systems perpetuate this violence and suffering, what’s the point of adhering to any of them? Why not transgress? What is the moral worth of drugs? Of the law? Of property? Of the poor? Of the rich? Like a kind of ethical black hole, everything that Omar comes into contact with is obscured, leaving much open-ended, allowing the logic of the street to break down just as easily as the justice of the law.

However, the emotion and hidden heart of Omar, the incredibly deep moments of pain and heartache, and the touching moments of joy and humanity, all give a glimpse, however mediated, into the boundless depths of anyone who chooses to go against what they deem to be hell. For McNulty, hell was letting “good police work” be eclipsed by bureaucratic inefficiency and corruption. For Bodie, hell was succumbing to Marlo’s incessant psychopathy, leaving the rules of the street to rot under the sun of a new day. And perhaps hell for Omar was waiting around on some derelict Baltimore corner, slinging crack rock for pennies and praying some stray bullet wouldn’t come crack his skull open. Maybe his hell was falling victim to a game too hard to play and too hard easy to lose.

“…And claim some corners, crews without guns are goners;
In broad daylight, stickup kids—they run up on us…”

So where does Omar fit into this narrative of uncompromising (neo)realism and institutional authority? Is a lone gun-slinging, duster-wearing Black cowboy of the Baltimore concrete a true representation of the reality the show’s creator and writers tried to portray? I personally have no idea whether or not Omar is a realistic character, since, growing up in coastal Southern California, there’s actually a surprising shortage of gun-slinging, duster-wearing Black cowboys. But if I were to hear of this character, or see a rundown written out somewhere, it would sound fairly theatrical to me. However, it is a fact that Omar is a proper amalgamation of a true-to-life phenomenon of the stickup boy, and moreover, the only character in the entirety of the show who elevates his own moral code above that of a system of power—a privilege afforded to him by the nature of his role.

“’Stickup boys,’ as they’re known in the criminal lexicon,” The Baltimore Sun wrote, “represent a niche in particularly chaotic and thriving drug markets in cities like Baltimore. Their dangerous schemes promise a quick buck, but also the possibility of a sudden death.”

What is at once a violent and unpredictable gambit, the drug trade is made all the more with the element of stickup boys. Moreover, in the same piece, The Sun also reported that after pulling off what is known as the “Boston Miracle” in the 1990s, the successful and systematic reduction of crime in the city of Boston, criminologist David Kennedy attempted a similar feat in Baltimore, only to be met with a force as formidable as it was shocking and (seemingly) insurmountable. As it happened, dudes like Omar Little were, in part, to blame. Moreover, it was found to be extremely difficult to curb the violence and drug trafficking in Baltimore when “the door gets kicked-in on a stash house before sunup,” and “the targets don’t know whether the intruders are undercover cops on a raid or someone looking to shoot everyone with a sawed-off shotgun.” According to The Sun, although Kennedy claimed to have encountered the stickup boy phenomenon elsewhere, in places such as Oakland and Detroit, he maintains that they are an element of “the worst kind of out-of-control drug markets.” A product of saturated violence. And this capillary quality of the stickup boy, their ability to blend into the trauma and chaos like a lethal pathogen in a crowded room, added to the ongoing problem just as corruption does for political theatre.

Although an obscure subject, culturally, we have been aware of the stickup boy for quite some time—and we have the darkly esoteric avenues of hip-hop to thank for that. Like anything American culture has come to adopt or take notice of in the last thirty years, hip-hop has really provided the most comprehensive portrait of the stickup boy as exists outside of The Wire, not to mention that it adds validity to Omar as a character.

One obvious example—if you just type in “stickup boys” into your Google search bar—is Don Biggavelli Max B’s, “stickup Boyz, ” featuring French Montana on the hook. The song itself is fairly unremarkable—horns and thick synth lines make up the backdrop, along with snappy 808 hits and sustained bass—but it’s the Silver Surfer, so the joint is at least wavey enough to make mention. There are also plenty of mentions, though not overtly so, throughout the vast landscape of Memphis tapes, Freddie Gibbs’ discography, the “nihilism” and fear of Chicago drill, as well as Atlanta’s Que, in which he refers to himself being “a stickup kid,” the lingo sometimes adopted in other situations. And even the PBS Frontline documentary, “Stickup Kid,” the story of Alonza Thomas, a 15-year-old kid tried as an adult for sticking up a gas station, adds to the popular glossary of the subject.

While the Max B song references it loosely, and other examples don’t necessarily call them out by name, another, more lyrically poignant artist writes an overt bar directly mentioning and describing the perils of a stickup boy in perhaps the most famous mention in hip-hop history. And that artist would, of course, be Nas on “N.Y. State of Mind.” The bar goes:

It’s like the game ain’t the same,
Got younger n***s pulling the triggers, bringing fame to their name;
And claim some corners, crews without guns are goners,
In broad daylight, stickup kids—they run up on us.
4-5’s and gauges, Macs, in fact,
Same n***s will catch a back-to-back, snatching your cracks in black—

In these few lines, Nas manages a portrait of a stickup boy—or kid, as he says—and the lethal relationship they have with “crews” and “corners.” They perpetuate violence, creating an atmosphere of fear and retaliation. However, Nas, in his incisive manner, also manages to call into question the whole entire game—if you’ll recall the essence of the entire song—and the crucial, deadly role the stickup boy plays. Stickup kids are just part of the context in this story, albeit a necessary element to examine, as Nas and The Wire are both keen on.

Another individual is also responsible for pushing the scholarship and literature of the stickup boy—and beyond just the limits of hip-hop. University of California, Riverside Professor of Sociology Randolph Contreras authored a book in 2012 titled, The Stickup Kids: Drugs, Violence, and the American Dream, an ethnography of a crew of stickup kids from the South Bronx. According to The Toronto Star, Contreras has a vested interest in ensuring that the stickup boy is not only part of the context in analyzing the war on drugs for the sake of scholarship, but for personal reasons tied to his youth. The Star reported that Contreras was born and grew up in the South Bronx during the ‘70s and ‘80s to Dominican parents. At the time he was coming up, crack cocaine and structural economic hardship rendered what was once a thriving borough of the city into a “cauldron of pain and resilience.” Eventually, Contreras and his friends dropped everything and began selling crack because “it seemed sensible at the time: all those he knew with real jobs were poor.” However, the war on drugs was at an all time boiling point, and it made it hard to break into the ever-shrinking crack cocaine market—they came up with another plan.

“So when the crack market dried up and the cash disappeared,” The Star wrote, “Contreras makes clear that his friends adopted a violent business model best suited to their skills and limited options: they robbed drug dealers. They called themselves joloperos—stickup kids.”

Such a real-world account of the cognition and development of a stickup boy adds to the impact of what Nas was rapping about. It also adds to the mythos of Omar—the reality and grit of the character, granting him an anchor in this world and ensuring his respect in the fictional portrayal.

“It’s tragic that he’s gone.”
Terry Gross of NPR’s ‘Fresh Air’

The first report I read of Williams’ death gave no conclusive cause of death. It was demoralizing enough just to know that he had passed away. However, of course, now, police sources have confirmed that it was a drug overdose. Heroin, they say—but what they mean is fentanyl. A fate that, personally, hit very close to home—I lost a good friend recently to the same drug, and have lost track over the years of how many others I’ve known who have passed.

During an interview with Terry Gross for NPR’s Fresh Air, Williams provided further insight into the soul behind Omar:

“I play Omar from a very painful place. You know, it’s a very dark state of mind to be in, a very painful state of mind. And that’s—I identify a lot with him on that level, you know, having overcome a lot of pain in life … So, you know, Omar in my book and my eyes, I don’t play Omar as an alpha male, not one to beat on his chest. And he’s a very, very sensitive dude. He comes from a very humble place. You know, growing up in the hood, we always knew the quiet one, the one that would kind of go inside. That’s the one you kind of—you watch out for.”

An actor is a good actor when they can embody the character they are playing, almost like feasting on their psyche. Most of the best acting performances of all time—Heath Ledger as The Joker, Daniel Day Lewis as Daniel Plainview, Jack Nicholson as Jack Torrance—rely on method acting in order to convey to the audience the inner-workings of the character. However, the genius of Williams’ performance of Omar, is that—despite openly admitting that he could hardly take the character seriously at first, as he “couldn’t fathom that anyone…would run away from” him “in total fear”—he came from the same painful space. Having grappled with addiction for the better part of his life, there’s no doubt that what Williams said is true: playing Omar, for him, is “a very dark state of mind to be in, a very painful state of mind. And that’s—I identify a lot with him on that level, you know, having overcome a lot of pain in life.”

I will echo what Gross said at the end of the program where she replayed the aforementioned interview in saying that his loss is a true tragedy. There’s no sense in waxing philosophic about the woes of the drug problem, the many ways it is killing us and jeopardizing a new generation; but there is a sense that this was somehow preventable. And maybe this is a gesture of the most profoundly misplaced transference, but having waded through the world of addiction—both as an occupant and observer—there’s always more that could have been done. But it wasn’t for a lack of trying. Williams had had time of sobriety. In the Fresh Air interview he is quoted in saying that he sought the help of a reverend from the Christian Love Baptist Church during the filming of The Wire. But somewhere along the way, he must have fallen off again. Whatever it was that pushed him back into it, who knows. But what I do know is the pain and loneliness of that dark process. And that’s the tragedy.

There’s no doubting that Williams was a rare talent. He brought joy out of the portrayal of even the most sordid individuals, and embodied a true artist in the execution of characters who, if played by another soul, may have fallen on deaf, uninterested ears. It’s my hope that he, like so many of us, found solace and love in his work. I pray he found peace at least a few times here, in this life. And if that’s not the case, I hope he’s found it wherever he’s at now.


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