2 Years After The Wire, Michael K. Williams Played Another Iconic Gangster Character in This Period Drama With 92% on Rotten Tomatoes

Cable television revolutionized the medium at the turn of the 21st century, pushing the boundaries of what television could be. Its full potential wasn’t realized until the end of the ’90s, when its hit crime drama The Sopranos experimented with the TV form in a huge way. While fans know what The Sopranos did for TV, they might not realize that it wasn’t the only series ushering in the wave of cinematic television viewers are so accustomed to today. A few years into The Sopranos‘ impressive run, another crime series debuted in 2002 that capitalized on the new cable format. While David Chase and Co. were telling a distinct story of a family, David Simon was telling the story of a city in The Wire.

The Wire deserves a lot of credit for helping to change the TV form as it continued to prove that TV was beginning to look and feel a lot more like cinema. What it often gets credit for is its utilization of POV, as the series never had a real protagonist outside of Baltimore itself. The city was explored on every level as the seasons went on, with cops, criminals, and politicians being some of the main areas of focus. In later seasons, the school system and the press were also explored at great length. This provided viewers with a comprehensive view of the city and what made it distinctive. However, within every environment depicted in Baltimore, compelling characters drove every individual storyline forward. Of all the characters, Omar Little was arguably the best, and the late Michael K. Williams portrayed him with incredible skill and complexity. However, just a couple of years after The Wire, he did it again with another character in another crime series.

Omar Little Is One of the Most Iconic TV Characters Ever

What really separated The Wire from other gangster shows during cinematic TV’s «golden age» was the approach and execution of telling the story. No one character ever felt like the main driving force of events in the series, as multiple characters had a huge impact on their personal environments. McNulty was a big presence among the police, Carcetti stole the spotlight among politicians, and Michael Lee became a greater influence on his classmates throughout the school storyline. However, no character had as much impact in the series as Omar Little did. The most creative aspect of Omar’s role in the show was that he was the lone wolf archetype of the series.

Every other character fits into a larger cog in the machine in some way, while Omar drifted through Baltimore with his own distinct rules and code that was separate from everything else. Omar was a key character in the criminal arena of the series, where powerful drug dealers like Avon Barksdale, Russell «Stringer» Bell, and Marlo Stanfield ran «the game» and made the rules. This is why Omar Little was so popular among fans, because he played «the game» his way, making up his own rules for his own survival. This would naturally lead to Omar being caught in the middle of various turf wars as well as being a target for the leading gangsters in town.

Omar Little was not a drug dealer like most criminals portrayed in the series, but instead a master thief and mercenary presence. Omar had no crew, no corner and no chain of command as he made his own rules that allowed him to thrive as well as survive within the criminal environment of Baltimore. However, as integral to the story as Omar is, a lot of credit has to be given to two people in particular for why Omar was such a dynamic presence in TV history. David Simon wrote a wild card player into the game he crafted, making Omar different from other characters on The Wire. This made Omar’s arc more appealing as audiences rooted for him to overcome the system he was actively battling against. It also made him a metaphor for what it means to rebel against the capitalist system in America when it isn’t working.

With all of this being said, Omar would be nothing without the perfect performer to play him. Michael K. Williams is probably one of the most underrated actors of his generation, simply due to his legendary presence on television being overlooked by whatever great talents were thriving in the feature film industry at the same time. Williams was a special actor who audiences will surely miss, as he had a way of playing distinct characters that transcended those around him. Williams brought Omar to life with a confidence and aura that is truly unmatched.

His line delivery often stands out in The Wire with iconic quotes like «But the game is out there, and it’s either play or get played» and «It ain’t what you takin’ but who you takin from.» Yet, what might be Williams’ biggest accomplishment is that he played another epic gangster character just two years after The Wire ended.

Michael K. Williams Also Played Chalky White in Boardwalk Empire

During the 2000s, there was an incredible run of crime shows that have come to define TV as audiences know it today. The Sopranos and The Wire were the first, but throughout the initial fifteen years of cinematic television’s reign, instant classics like The Shield, Breaking Bad, Sons of Anarchy, Dexter, Weeds and Deadwood were essential landmark shows that paved the way for the future of the medium. Another one that was incredibly impactful was Boardwalk Empire, which provided a great hook for audiences that revolved around prohibition-era gangsters.

Steve Buscemi plays «Nucky» Thompson, a New Jersey figure who leads a double life as a bootlegger and politician throughout the 1920s. One of the show’s most memorable qualities was the inclusion of a unique ensemble and characters ranging from big-shot politicians to low-level gangsters. What made these characters even more unique is that they were often based on real-life historical figures from the Prohibition era in America. Whether it was Al Capone, Lucky Luciano or Joseph Kennedy, iconic faces always showed up throughout the series. One of Nucky’s greatest allies in the story is Albert «Chalky» White, who is loosely based on a real-life boxer with a distinct background. Chalky is a bootlegger in Atlantic City, New Jersey, and the unofficial leader of the African-American community in town.

Similarly to The Wire, Boardwalk Empire’s creator, Terence Winter, deserves considerable credit for the way he constructed the series. Every major character is given a sufficient arc throughout the series, and at times, specific characters take center stage in individual seasons. Chalky White is immediately portrayed as an important figure who is not to be underestimated. Chalky is clever, tough and, most importantly, loyal. Despite having differences with Nucky at times, the two characters share a mutual respect and a solid, loyal bond to one another throughout the series.

​​​​​​​In many ways, Nucky and Chalky run Atlantic City together, keeping everyone in line and fending off enemies that challenge their businesses. Their relationship is greatly tested in season four, which focuses heavily on Chalky’s arc as he battles a gangster looking to usurp his hold over the African-American community in New Jersey. Nonetheless, Chalky comes out on top in the war, but it costs him greatly.

Chalky’s greatest attribute proves to be his loyalty, as he remains the greatest ally Nucky has until the very end of the series. Chalky goes through a lot and eventually obtains the ending he deserves in disheartening and poetic fashion. Similarly, like The Wire, it is Michael K. Williams’ performance that makes all the difference. Williams embodies what makes Chalky different from Omar by being a man who plays by the rules and manipulates them to his benefit when necessary. Once Winter focuses the story even more on Chalky’s arc, the emotional connection audiences feel to Chalky comes through his devotion to his family, and Williams evokes this emotional connection to the fullest extent. While Chalky never became the most memorable character on the show, he was still one of the most iconic in the «golden age» of TV.

Omar and Chalky Represent an Important Dichotomy In Exploring Criminality

Michael K. Williams essentially shined as an actor and proved his versatility by portraying two different kinds of gangster figures on TV. Omar and Chalky both represent criminality in America, but do so in different ways. It is a huge credit to Williams for being able to embody these differences and still make the same point about American society.

Criminality is always rooted in places of survival, desperation, greed and defiance. Both Omar and Chalky express these important themes, but portray different layers of them. While greed is inevitable in the life of a criminal, Omar comes from a place of defiant desperation, as his environment has shaped him into a specific kind of presence in Baltimore.

Meanwhile, Chalky (who represents these qualities in an older American society) embodies the idea that greed corrupts all. In the end, Chalky causes a great deal of chaos around him due to his selfish pursuit of maintaining power and influence. Omar didn’t need power to survive, but it came to be Chalky’s greatest flaw. In both instances, these tragic figures are a product of the «American dream» and how criminality derives from a place of defiance against the oppressive systems of American capitalism.

Despite being decades apart, Omar and Chalky share a common thread, and the characters’ similar fates convey a deeper message about the world. Michael K. Williams was a once-in-a-lifetime actor, not because he could take on any kind of role and have an impact, but because he took on two similar roles and had the same impact twice. Both shows are classics of cinematic television and should be remembered for many things. Michael K. Williams is just one of the most memorable things.

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  The Wire

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    Dominic West Jimmy McNulty

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    Lance Reddick Cedric Daniels

  The Baltimore drug scene, as seen through the eyes of drug dealers and law enforcement.

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  Boardwalk Empire

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    Shea Whigham

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    Kelly Macdonald

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    Stephen Graham

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    Steve Buscemi

  An Atlantic City politician plays both sides of the law by conspiring with gangsters during the Prohibition era.

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