For roughly two decades, Michael K. Williams’ career exploded on the small screen. While the Emmy-nominated actor’s career really started in the music videos he appeared in and choreographed (he told Complex back in 2017 that he’d choreographed Crystal Waters’ “100% Pure Love” video), it wasn’t until the early 2000s when Williams really started hitting his stride. He’d sink his teeth into characters that felt larger than life; even if he felt typecast, that was only because he was so damn good at breathing life into these characters. That scar across his face and his raspy voice may have been perfect for some of the more sinister figures he’s portrayed, but on the inside, his intellect and compassion for good material forced him to put on, every time he hit the stage. He had a gift, and through the medium of television, we were able to see him live in these characters for seasons, adding layers of beauty to every line read, wasting no movements, and always scoring.
Michael K. Williams defied the odds, taking on the role of The Wire’s Omar Little and becoming an icon. He then followed that up with equally impressive work on the acclaimed Boardwalk Empire. These two series helped further establish HBO as an impact player in the world of producing original TV, and much of that is credited to the performers they choose to put in these roles. It’s tough to recall too many performers of his time that were as consistent as Williams was. He could have you crying one moment, then, with a quick smile and a one-liner, have you crying from laughing. The world has truly lost a gem.
The shock of Williams’ death is going to be felt for a bit. Many of us routinely binge The Wire, one of the greatest televisions shows of all time. The Primetime Emmys are in two weeks; Williams is currently up for an Emmy for his work on HBO’s Lovecraft Country. He’d just booked a role in the upcoming George Foreman biopic. For the last two decades, we’ve known that if Michael K. Williams was in it, he was going to bring that fire—for us. Williams was a man of the people; just take a look at how those who loved him and enjoyed his work speak about what he meant to the game and in their lives. That’s why we’d like to highlight some of his finest television work of the last 20 years.
'The Sopranos'
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Character: Ray-Ray
Appeared: “Army of One” (Season 3, Episode 13)
Where to Watch: HBO Max
While not his first acting gig, nor his first TV work, Williams appeared on the Season 3 finale of The Sopranos, “Army of One” (a.k.a. the one where Jackie Jr. gets what’s coming to him), 20 summers ago. After Jackie Jr. gets into some hot water after failing to stick-up a card game, he has to hide out in the projects. Heading over to Boonton, Jackie Jr. stays with Ray-Ray (Williams) and Ray-Ray’s daughter, who fails to teach Jackie Jr. how to play chess (which is a brilliant way of highlighting just how ill-equipped the younger Aprile was for this mob life). It’s in this same Boonton project that Jackie Jr. meets his demise. We never see Ray-Ray again in The Sopranos, but that might be because he was about to embark on one of his career-defining roles.
'The Wire'
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Character: Omar Little
Appeared: Seasons 1-5
Where to Watch: HBO Max
Many would say that Williams’ portrayal of Omar Little is his greatest work. They wouldn’t be wrong, although we imagine some fans of other HBO series would beg to differ. The chants of “Omar coming!” during Season 1 of The Wire usually indicated that Omar, decked out in an ankle-length black trenchcoat to conceal the shottie he always toted, was indeed on the way to handle some business… a.k.a. stealing drugs from drug dealers to make his way. It was a dangerous lifestyle, and he wore his role in the game with pride, carrying a code (he didn’t curse) and honor way past the Barksdale beef that consumed his being for his run on the series. It was a complex character—it was rare to see a series like this feature a homosexual drug thief as one of its most beloved characters, but that was all due to how Williams carried it. And how he delivered every line. If you haven’t watched The Wire yet, rectify that, if for nothing more than to see a role that Williams deserved some Emmy love for.
'Boardwalk Empire'
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Character: Albert “Chalky” White
Appeared: Seasons 1-5
Where to Watch: HBO Max
It may start looking like Michael K. Williams only worked for HBO, but part of that is because a) Williams was on fire and b) HBO was good with keeping amazing talent around. “Coming from The Wire and going to work on Boardwalk Empire is like lightning striking in the same place twice,” Williams told The Baltimore Sun in 2011. “I’ve been so fortunate to have these roles.” Fortunate is one thing, but it felt like the work Williams put in more than made him fit for these opportunities. Williams’ calm yet dangerous demeanor fit perfectly into the role of Chalky White, who controlled the Black crime trade in Atlantic City during this Prohibition Era-set crime drama. Chalky came out swinging early, taking over operations and taking out the Klan while giving fans a new debate topic: Omar or Chalky? In Williams’ words, Chalky was “iconic,” again telling The Baltimore Sun that, “For me to portray a prominent, strong black man who’s successful in 1920 is such an homage to my ancestors and to the struggle and pain of my family members who walked before me. To get to portray this character with class and dignity and strength is a humbling experience, and I’m really grateful to be given the opportunity.”
Williams’ work as Chalky White is also important, as it was the first role to grant him an acting award: He won the Screen Actors Guild Award for Outstanding Performance by an Ensemble in a Drama Series as a part of the Boardwalk cast in 2011. He was also nominated for an NAACP Image Award for Outstanding Supporting Actor in a Drama Series.
'Hap and Leonard'
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Character: Leonard Pine
Appeared: Seasons 1-3
Where to Watch: Netflix
While not a mainstream TV hit (possibly due to it airing mostly on Sundance TV instead of a bigger channel), the three-season Hap and Leonard might be up your alley. Williams plays Leonard Pine, a gay Vietnam war vet who, as you can see in the above clip, is unafraid to both be himself and dish out a little lesson in respect. The offbeat comedy is set in the 1980s, and is based on writer Joe R. Lansdale’s Hap and Leonard book series. The show is an ill series of violence, comedy, and dope characters; it was perfect for Williams to really stretch out and have some fun in. With each season being six episodes, this could be an underrated gem for the right viewer out there.
'When They See Us'
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Character: Bobby McCray
Appeared: Season 1 (limited series)
Where to Watch: Netflix
“When the police want what they want, they will do anything.” Those words were uttered by Williams as he portrayed Bobby McCray, Antron McCray’s father. Antron was of course one of the Black boys dubbed “The Central Park Five,” who were falsely accused of (and prosecuted for) the rape of a jogger running through Central Park in 1989. The Ava DuVernay-directed series brought us inside the prisons and court rooms and personal lives of these Black boys and their families. The above scene is one where Williams channels the anger and frustration of someone who understands the system and wants to help his son navigate it unscathed; it’s tough to see. While first playing it calm, McCray’s anger and frustration boils over. It’s a powerful scene, and one that puts Williams’ ability to fully amplify our voices on full display.
'Lovecraft Country'
![Character: Montrose Freeman
Appeared: Season 1 (limited series)
Where to Watch: HBO Max
Prior to the release of Lovecraft Country, I got to be a part of a press roundtable interview with Michael K. Williams about his work as Montrose Freeman on Lovecraft Country. In a complex series (it’s literally a melting pot of genres focused around a Jim Crow-era tale of a Black man battling Lovecraft monsters and the monsters of the racist South), Williams plays a complex, stubborn man. Williams’ Montrose Freeman is a closeted Black man dealing with his own internalized homophobia and how to be who he is in the world. His relationship with his son is strained, and through this adventure, he learns a lot about his father.
Anyways, during this junket, I only got one question to ask Williams, due to the format. I’d asked him if he had purposefully taken on back-to-back Black father roles, or if that was just how the ball bounced. “I don’t get caught up in telling Black stories,” Williams expressed. “I tell good stories from the Black experience, so it just… We’re all human.” It gets deeper than that, though, as Williams realized that maybe he could use his gifts in a way that could help his people get to see what they may not have grown up with.
“In regards to the father figure roles,” Williams continued, “I’m a man of a certain age and a lot of our children are young people that I consider my kids now, my young people. The family structure has been so severely ruined due to mass incarceration and drug addiction, poverty, you name it. These little girls have their mom for that bond and that identity thing to take the cue off of, but where are our young men getting that from when we’re not there? So to have a piece of art [that] explores what a father/son relationship looks like in the Black community with all of the issues that come with it, right now, is powerful. Especially right now.”
Williams’ work on Lovecraft earned him a Primetime Emmy Award for Outstanding Supporting Actor in a Drama Series nomination; he already won the Critics’ Choice Television Award for Best Supporting Actor in a Drama Series. With the Emmys just a few weeks away, Williams quite possibly could net a posthumous Emmy win.](https://img.youtube.com/vi/Mp4_XYzKakQ/mqdefault.jpg)
View this video on YouTube
Character: Montrose Freeman
Appeared: Season 1 (limited series)
Where to Watch: HBO Max
Prior to the release of Lovecraft Country, I got to be a part of a press roundtable interview with Michael K. Williams about his work as Montrose Freeman on Lovecraft Country. In a complex series (it’s literally a melting pot of genres focused around a Jim Crow-era tale of a Black man battling Lovecraft monsters and the monsters of the racist South), Williams plays a complex, stubborn man. Williams’ Montrose Freeman is a closeted Black man dealing with his own internalized homophobia and how to be who he is in the world. His relationship with his son is strained, and through this adventure, he learns a lot about his father.
Anyways, during this junket, I only got one question to ask Williams, due to the format. I’d asked him if he had purposefully taken on back-to-back Black father roles, or if that was just how the ball bounced. “I don’t get caught up in telling Black stories,” Williams expressed. “I tell good stories from the Black experience, so it just… We’re all human.” It gets deeper than that, though, as Williams realized that maybe he could use his gifts in a way that could help his people get to see what they may not have grown up with.
“In regards to the father figure roles,” Williams continued, “I’m a man of a certain age and a lot of our children are young people that I consider my kids now, my young people. The family structure has been so severely ruined due to mass incarceration and drug addiction, poverty, you name it. These little girls have their mom for that bond and that identity thing to take the cue off of, but where are our young men getting that from when we’re not there? So to have a piece of art [that] explores what a father/son relationship looks like in the Black community with all of the issues that come with it, right now, is powerful. Especially right now.”
Williams’ work on Lovecraft earned him a Primetime Emmy Award for Outstanding Supporting Actor in a Drama Series nomination; he already won the Critics’ Choice Television Award for Best Supporting Actor in a Drama Series. With the Emmys just a few weeks away, Williams quite possibly could net a posthumous Emmy win.
