“The Wire”’s Omar Little was the most memorable character on one of the greatest shows in the history of television. The actor who played him, Michael Kenneth Williams, was also one of the best and most versatile character actors of this—or any—generation. Neither of these statements are hyperbole; a glance at his over one hundred roles reveals his versatility and his daring. When he graced the screen with his piercing stare and his expressive face, he could enliven even the most extraneous of roles. For example, his father in John Leguizamo’s entertaining chess drama, “Critical Thinking” is an unnecessary character, the angry Dad cliché whose own kid can do no right. Yet Williams’ presence is welcome and, in one scene, he subtly suggests personal change in a wholly unexpected, yet realistic way that stuck with me despite my misgivings. He had an uncanny power to disarm, to zig when you think he will zag. He kept things interesting.
Everyone has actors they look forward to seeing, if only for the fleetest of moments, and Williams more than earned that anticipation. Creating one iconic character is enough to solidify a career and to sear a bit of legend into one’s legacy. Williams created at least two icons, adding “Boardwalk Empire”’s Chalky White to his wall of fame. He went from back-up dancer to five-time Emmy nominee, never once betraying his own personal truth and methodology. That’s why his sudden and unexpected transition from this life on September 6, 2021 hurts so much. We can look down the road and imagine what could have been, and what never will be.
The loss is even more painful if one considers how candid and brutally honest Michael Kenneth Williams was with his audience. In this must-watch Vanity Fair video, he leans into how important it is have the type of representation he puts onscreen. His descriptions merge his real-life struggles with his art, and he explains how that art provided a necessary outlet to deal with those issues. For those entrenched in the life that shaped Omar Little, this level of candor invited the character into their hearts and minds. In a 2012 interview, Williams talked about a low point with drugs in Newark, New Jersey, where some people brought him to a well-known pastor who mentored and assisted people in crisis. “Omar needs help,” everyone kept telling the reverend. When Williams revealed his name was Mike, the pastor asked “Who the hell is Omar?” He had no idea. But the streets knew, and those streets tended to one of their own. Williams said he never forgot that, and it inspired him to continuously pay forward the kindness he received.
He earned his debut movie role opposite Mickey Rourke and the late Tupac Shakur in 1996's "Bullet," after ‘Pac saw a picture of Williams’ newly scarred visage (a trademark earned on his 25th birthday) and thought “he looks tough enough to play my little brother.” Never mind that Williams was older; a movie career was born. Soon after, the actor impressed Martin Scorsese during an audition for the underrated “Bringing Out the Dead,” cycling through three different emotional roles consecutively. “Give him whichever role he wants!” Marty told the casting director. As a producer on “Boardwalk Empire,” Scorsese would remember the actor later, casting him as fellow gangster Chalky White opposite Steve Buscemi. This role was enough to cement HBO immortality, but of course, that had already been obtained by “The Wire” and, to a lesser extent, a small role on “The Sopranos.”
Every ensemble benefitted from his presence. In Ava DuVernay’s excellent miniseries about The Exonerated Five, “When They See Us,” Williams is the first episode’s MVP, delivering a heartbreaking, terrifying, and infuriating performance as the father of Anton McCray. This is a man whose understandable fear of police brutality and the possible murder of his son by the NYPD leads him to an act of desperation that has horrific repercussions. These scenes play in stark contrast to the opening moments where Mr. McCray bonds with his son while Special Ed’s “I Got It Made” plays on the soundtrack. The performance is one of extremes, but you can see the same love in Williams’ eyes when he’s ribbing Anton about sports as when he’s demanding he lie and tell the cops what they want to hear. Not many actors can channel such rich layers of conflict with their faces alone.
In the lousy Mark Wahlberg remake of “The Gambler,” Williams is part of a fantastic supporting ensemble along with John Goodman and Alvin Ing. They’re a trio of “bad guys” with whom Wahlberg’s lead is constantly in hock, and they trample the star in every scene they’re in. You wish the film were just those three villains sitting around and swapping war stories instead of having to deal with the whims of a dismal lead performance. The movie is a reunion of sorts between Williams and Wahlberg; back in the days of Marky Mark and the Funky Bunch, they shared music video space together. Speaking of music videos, Williams choreographed and danced in “100% Pure Love,” the best song by Keith Sweat’s sole competition for R&B Whiner of All Time, Crystal Waters.
As in real life, Williams played onscreen mentors and friends to those in the game. Director X’s “SuperFly” remakes the original with the actor in the Carl Lee role as Youngblood Priest’s partner in crime. In the series “Hap and Leonard,” he’s one-half of a friendly duo navigating the waters of a pitch-black comic noir. And in the HBO miniseries “The Night Of,” writer Richard Price and director Steven Zaillian create a juicy role for him opposite Emmy winner Riz Ahmed. Of this performance, Williams said it gave him an unnerving insight into the world his nephew inhabited during his incarceration. Like everything else he learned for, or brought to the role, it shows in the work.
There are so many other performances I could cite, like his comic work on “Community” or his superb work as real-life gay activist Ken Jones in “When We Rise,” the miniseries that first put him in collaboration with his “Lovecraft Country” co-star, Jonathan Majors. His work opposite Queen Latifah’s brilliant performance in “Bessie” remains one of my favorite Williams creations. Hell, he’s even in the 2016 “Ghostbusters” remake! But I must say a few words about the role he’ll be most remembered.
Omar Little is a lot more than the description I keep reading in other tributes. They call him a “shotgun-toting homosexual thug who robbed drug dealers.” Every word in that phrase is hotwired for maximum shock value and nothing more. Little’s sexuality, for example, was certainly a new angle for the type of character that’s stereotypically straight, but it wasn’t shocking to me because the toughest guy in my ‘hood growing up was gay. People stepped to him not because of who he loved, but what he represented—a powerful figure to be feared until the moment someone can take him down. With that knowledge in my head, Omar’s ultimate fate played as an expected anticlimax rather than a startling jolt. He had to “go out like that.”
Until that moment, Williams, “The Wire” creator David Simon, the writers and that incredible ensemble of actors, help elevate Omar Little to greatness. The words he’s given to say, his trademark whistling, his unbreakable code that seemed to come from the actor as some unapologetically Black form of the Method (ditto his occasional tenderness), and the complex plotlines and relationships all work together flawlessly to create something far richer than “a shotgun-toting thug.” The result was some fantastic showdowns between Omar and other characters like Brother Mouzone, moments that sounded like poetry and felt as tense as taut wire. Omar Little’s ascension into the pantheon of television’s most memorable characters is well earned, especially when you consider just how good the other characters on “The Wire” really were.
And Omar was infinitely quotable. Perhaps his most famous quote was an encapsulation of his philosophy: “It ain't what you takin', it's who you takin' from, ya feel me? How you expect to run with the wolves come night when you spend all day sparring with puppies.”
Had the Emmys been paying attention, Williams would have earned more than one award for playing Omar. They did nominate him for other roles five times, however, including a standing nomination for “Lovecraft Country” that could finally net him a trophy posthumously. For now, we need to meditate on how such a great talent could be gone so soon. When asked how he’d like to be remembered, Michael Kenneth Williams said “as one cool-ass dude, you know? Someone who cared. And I would never want anyone to say, ‘Oh, he forget where he came from.’” We know he didn’t forget. And we’ll remember this cool-ass dude. Rest in peace.