Remembering Michael K. Williams: How to watch his most memorable roles

Michael K. Williams
(Image credit: Photo by Rodin Eckenroth/FilmMagic)

Actor Michael K. Williams died at the age of 54 on Monday, Sept. 6. Williams was a fixture on a multitude of HBO series, including his most famous role as Omar Little in the classic crime series The Wire, however he lent his talents to both the big and small screen, comedy and drama, and in more recent years documentary work.

Williams’ career began as a dancer in music videos before he got his first credited acting job in Bullet, a crime drama that starred Mickey Rourke and Tupac Shakur. He would appear in Martin Scoresese’s Bringing Out the Dead and an episode The Sopranos, as well as a number of other small credits, before landing the role of Omar Little on The Wire in 2002, where he quickly became recognizable, not least of all for his facial scar (which he got in a knife fight when he was 25). 

Other TV roles included a brief run on Alias, playing 1920s gangster Chalky White in Boardwalk Empire and memorable roles in miniseries and TV movies like Bessie, The Night Of and When They See Us. He also was part of the titular comedic duo of Hap and Leonard.

On the film side, Williams was a fantastic supporting actor with roles in films like Gone Baby Gone, The Road, 12 Years a Slave, Inherent Vice, Kill the Messenger, Ghostbusters (2016) and more. According to IMDb, there are two films that Williams completed and will be released sometime in the near future called Surrounded and 892.

The actor was also branching out into some non-fiction work, mostly with Vice on projects that included Black Market with Michael K. Williams, which dove into the world of illegal trading.

Williams was nominated five times for a Primetime Emmy, including a nomination for the upcoming 2021 awards for HBO’s Lovecraft Country. Surprisingly, despite it being his most iconic role, Williams was never nominated by the Emmys for his work in The Wire.

It’s sad to think that we will no longer have an actor of Williams’ caliber to entertain and enthrall us, but he leaves behind a legacy of great performances to enjoy. Here’s just some of them (many of them available on HBO Max).

The Wire (2002-2008)

The Wire Michael K. Williams

(Image credit: HBO)

Where else would we start but The Wire? Omar Little was a Baltimore stick-up man, who Williams described to the New York Times in 2017 as “this dark-skinned outspoken man in the hood who didn’t care what anyone thought of him. He is everything I wished I could be.” Williams’ performance was a fan-favorite in the series, touting his sawed-off shotgun, leading an openly gay lifestyle and having an aversion to cussing, far from the kind of stereotypes you can often see in crime dramas. This is the iconic role for Williams; the launching pad for all that would come later. 

Boardwalk Empire (2010-2014)

Boardwalk Empire Michael K. Williams

(Image credit: HBO)

A few years after the end of The Wire, Williams would turn in his shotgun and Baltimore for tweed suits in 1920s prohibition Atlantic city as the gangster Chalky White on Boardwalk Empire. White was a key ally for Steve Buscemi’s Nucky Thompson, helping to run the bootlegging operation. But because of the setting, Williams’ Chalky was using the means to try and further his, his family and his community’s place; his character and Williams’ portrayal were always highlights, giving an extra dimension to the series. 

12 Years a Slave (2013)

12 Years a Slave Michael K. Williams

(Image credit: 20th Century Fox)

Williams' time in 12 Years a Slave is short, as he plays another captured man who is being transported to the south to be sold into slavery alongside Chiwetel Ejiofor’s Solomon Northup - his character dies shortly after we meet him as he believed that he and his fellow captees should try and fight their way to freedom, tragically dying when he attempted to do so. However brief his time was in the film, Williams burns the screen, as practically everyone does in the ensemble, in this powerful, Oscar-winning film. 

Hap and Leonard (2016-2018)

Hap and Leonard

(Image credit: Sundance TV)

Hap and Leonard only ran for 18 episodes (three six-episode seasons), but it showcased a different side of Williams that many hadn’t seen, his comedic sensibilities. Starring as the latter half of the titular duo, Williams’ Leonard along with James Purefoy’s Hap go searching for buried treasure in some southern swamps, only to have to deal with Hap’s ex-wife, washed up revolutionaries, a pair of psychotic killers and the cops. 

When They See Us (2019)

When They See Us Michael K. Williams

(Image credit: Netflix)

When They See Us, Ava DuVernay’s epic depiction of the Central Park Five - a group of teenagers wrongly convicted of killing a woman in Central Park in the 1980s - is an emotionally wrenching story detailing the impact of such false accusations not only on the kids who were charged with them, but their families as well. Williams plays the father of one of the boys, Bobby McCray. Williams is devastating as a father scared for his son who convinces him to sign the false confession that led to his eventual conviction. Williams received his fourth career Emmy nomination for this role. 

Michael Balderston

Michael Balderston is a DC-based entertainment and assistant managing editor for What to Watch, who has previously written about the TV and movies with TV Technology, Awards Circuit and regional publications. Spending most of his time watching new movies at the theater or classics on TCM, some of Michael's favorite movies include Casablanca, Moulin Rouge!, Silence of the Lambs, Children of Men, One Flew Over the Cuckoos Nest and Star Wars. On the TV side he enjoys Only Murders in the Building, Yellowstone, The Boys, Game of Thrones and is always up for a Seinfeld rerun. Follow on Letterboxd.