Michael K. Williams’ 10 Best Roles, Ranked

The world of film and television suffered a major blow with the sudden passing of Michael Kenneth Williams, the supremely talented Emmy-nominated actor behind such iconic roles as Omar Little from The Wire and Chalky White from Boardwalk Empire, among others.

A terrific actor who made every project he was a part of better, Williams will be missed by not just his friends and family, but fans across the world as well. With a heavy heart and an air of genuine gratitude, it’s only right to look back and celebrate the creative legacy the talented actor left behind after 54 short years on Earth.

10 Tariq Khalil – Inherent Vice (2014)

Often cast in intensely dramatic roles, Williams showcased how funny he was in Paul Thomas Anderson’s 1970s-set stoner detective comedy Inherent Vice. After finishing the role of Tariq Khalil, Williams spoke at the New York Film Festival about how excited and nervous he was to come from the fast-paced world of TV and work with director Paul Thomas Anderson and lead actor Joaquin Phoenix, and how safe he felt in such a new process.

The result was a rare comedy performance that showcased the actor’s deadpan delivery and droll sense of humor. As the fictional leader of the Black Guerrilla Family, Williams effortlessly plays off of Phoenix’s stoned detective. It’s a small yet crucial performance that hinted at Williams’ previously untapped comedic potential.

9 Ken Jones – When We Rise (2017)

Another memorable performance was Williams’ searing turn as HIV-positive veteran and gay rights activist Ken Jones in the 8-part miniseries When We Rise. The show documented the compassion, humanity, and dogged determination to fight for equal rights for the LGBTQ+ community in 1970s San Francisco.

As Jones, Williams imbues the real-life activist with a warm and inclusive countenance, telling hivplusmag.com, “If I want to help heal my community, I don’t want to alienate the people in my community. It doesn’t work. I have to embrace everything, everyone.” This empathy comes through in his performance as he creates a relatable character who is simultaneously rigid in his quest for equality and compassionate in understanding the flaws of his friends and enemies.

8 Robert – 12 Years A Slave (2013)

In yet another important true story, Williams’ brought heartbreaking humanity to his role as Robert in the Best Picture-winning 12 Years A Slave. Despite limited screen time and minimal lines of dialogue, Williams is able to convey through his eyes and body language a long history of hurt and abuse, especially in the scene where he’s bound in the basement.

Robert also shows a level of dignity the other characters are too afraid to show, as he’d rather attempt an escape than continue to live in imprisonment. It’s a small role with a major impact on the film’s narrative as Robert helps Solomon (Chiwetel Ejiofor) decide how to safely maneuver through the plantation.

7 Leonard Pine – Hap & Leonard (2016 – 2018)

After Williams showcased his funny side in Inherent Vice, he was ideally cast in the role of Leonard Pine in the darkly comedic mystery series Hap & Leonard. As a Vietnam vet with severe anger management issues, Williams stole the show away from seasoned actors like James Purefoy and Brian Dennehy.

With 18 hour-long episodes to fully explore the character, Williams was afforded a substantial amount of time to portray the complex flaws and virtues of Lenard. In particular, Williams expertly communicated Leonard’s rage and frustration of being left behind by a society that no longer has any use for him. The believability of the character, mixed with Williams’ effortless comedic timing, resulted in a memorable performance that went largely unnoticed by critics and audiences alike.

6 Jack Gee – Bessie (2015)

With the added pressure of accurately portraying another real-life character, Williams earned his first Primetime Emmy and Satellite Award nominations for his role as Jack Gee in Bessie, the HBO musical biopic and one of Queen Latifah’s best movies. After marrying the popular blues singer Bessie Smith in 1923, Jack became his wife’s business manager, which created a rift between their business and pleasure as Bessie grew in popularity. Williams gives such a convincing performance as the insecure husband that he helped the film win an Emmy for Outstanding Television Movie.

5 Freddy Knight – The Night Of (2016)

Williams deservingly earned his second Primetime Emmy nomination for his commanding performance as Freddy Knight on the HBO miniseries The Night Of. As the highly intelligent prisoner who runs his own economy from the inside, Freddy goes out of his way to help a young man named Naz (Riz Ahmed) who may or may not be rightly booked for murder.

In addition to the forceful gravitas Williams demonstrates on screen as the prison’s alpha dog, it’s the moral ambiguity Freddy operates under that makes his character so fascinating. He sees himself in Nas and vows to help him avoid a similar path despite the damage done to his intimidating reputation in prison.

4 Bobby McCray – When They See Us (2019)

It’s clear that Williams was a socially conscious actor who aligned himself with important, real-life stories that can make a difference. As such, he earned his fourth Primetime Emmy nod for his role as Bobby McCray, the compassionate father of Antron McCray, one of the five wrongfully accused Central Park Five Members in one of Netflix’s best miniseries, When They See Us.

Directed by Ava DuVernay, the notorious miscarriage of justice underscores the odious racial profiling and deep-seated discrimination in the legal system, with McCray at the forefront of voicing the need for change. As the frustrated father, Williams creates a convincing portrait of a parent desperate to save his son from being jailed for a crime he didn’t commit.

3 Montrose Freeman – Lovecraft Country (2020)

The profound sadness of Williams’ passing is compounded by the fact he just earned his fifth and most recent Primetime Emmy nod for his role as Montrose Freeman in the HBO original series Lovecraft Country. As Atticus’ (Jonathan Majors) obstinate and opinionated father, the tough love he shows actually steels the young man for the perilous monsters to come.

Of course, the entire premise of the series involves Atticus’ search for Montrose, which takes him on a harrowing sojourn through the American landscape in the 1950s with his companion Leti (Jurnee Smollett). The depth and dimensionality of Monstrose are matched by his parabolic character arc as a loving father who must confront his past to forge a better future for his son.

2 Chalky White – Boardwalk Empire (2010 – 2014)

With 56 episodes aired between 2010 to 2014, Albert “Chalky” White is the longest performance Williams gave in his illustrious career. With a peerlessly powerful screen presence, the likable Boardwalk Empire racketeer was not only a loyal affiliate of Nucky Thompson (Steve Buscemi), but he was the de facto spokesman for the Black community as a whole during a time of severe oppression and discrimination.

With years of preparation and hours of screen time to fully flesh out the character, the historical import of the character is only outdone by Williams’ splendid characterization that never feels cliched or stereotypical. Williams never lets the audience forget that while Chalky is flawed and makes mistakes, he’s still a decent man trying his nest to navigate the deadly gang wars of Depression-era Atlantic City.

1 Omar Little – The Wire (2002 – 2008)

A landmark character in a watershed TV show, Williams completely redefined what TV villains looked like when he assumed the role of Omar Little on HBO’s hit crime drama The Wire. Genuinely terrifying and endearingly tender at once, Omar is a Baltimore stick-up man feared by anyone on either side of the law that dares to cross his path.

With his trademark facial scar, large duster concealing an arsenal of weaponry, and whistling “A-Hunting We Will Go” as he calmly stalks his enemies, Omar’s frightful demeanor is countered by the surprisingly intimate moments he has with his grandmother, his male lovers, and refusal to kill innocent bystanders. Shattering stereotypes across the board in the most authentic way imaginable, Omar Little will likely remain Michael Kenneth Williams’ finest acting role and one of the best performances in the new Golden Age of Television.