A Love Letter To Omar Little And The Man Who Made Him
Credit: Paul Schiraldi/HBO

Working as a background dancer in music videos was how the late Michael K. Williams entered the entertainment industry—but it was his portrayal of a freelance stickup man in Baltimore that made him a star of historic and narrative-shifting proportions. 

As many have long professed, there is more than one way to be gay. Still, when it comes to how gay Black men are portrayed on screen, our depictions have too often been drowned in conventional stereotyping. Many actors have lent their talents to the act of changing this—but few characters have risen to the stature and success of Omar Little, the gay Black man who wielded a pistol against his enemies in The Wire

Omar first appeared in the third episode of season one of the HBO drama, which debuted on June 2, 2002. Customarily wearing a duster camouflaging a shotgun, a large caliber handgun and a bulletproof vest, he ominously whistled “The Farmer in the Dell” when approaching his targets. When bystanders saw him walking down the street, they’d shout “Omar comin’!” and run in fear—not of his queerness but his fearlessness. 

Credit:Paul Schiraldi/HBO

As ruthless as Omar could be, though, he operated with some semblance of morality, as evidenced by his refusal to harm civilians or even curse. There was also the tenderness he held for his grandmother, with whom he attended Sunday service each week. Omar was a sexual being, too—which is not always an easy feat for any gay character, much less one who is a Black male.  

Many Black men across the sexual spectrum are as complicated as Omar, but rarely has that complexity been shown on television. He provided visibility and, in the process, helped expand people’s minds about who a gay Black man could be. His portrayal was a direct testament to the talent and depth of Williams, the actor who brought him so powerfully to life.  

David Simon is the celebrated creator of The Wire, but it was Williams’s genius, commitment to his craft and general love for Black people that made Omar the defining character he was. As Simon himself wrote in an essay following Williams’s passing, the actor was consistently “weaving more depth and nuance into a character that he ultimately made iconic and timeless.” And when season two of The Wire shifted focus from the Baltimore projects to the docks, to concentrate on the issues of the White working class, it was Williams who challenged that decision. He reminded the writers that they were stewards of a show chronicling Black life in a predominantly Black city.  

“For me, Omar Little was the heartbeat of The Wire,” says writer–producer Kirk A. Moore, whose credits include For Life, American Crime and 13 Reasons Why. “He gave face and brought empathy to disenfranchised people. There was a humanity to him not often given to Black LGBTQ characters. He looked like the guys I dated. He felt normal. Omar didn’t feel like a ‘poster boy’ or some grand statement for all Black gay men.” 

Credit:Paul Schiraldi/HBO

After Omar died during season five of the show, in 2008, Williams continued to push queer Black male representation on television. This included his work on Lovecraft Country in the role of Montrose Freeman, who, unlike Omar Little, didn’t have the freedom to know whether he was gay, because he was trapped by what he thought a Black man was supposed to be. The same goes for his role as Leonard, a gay Black Republican East Texas veteran in the country-music business, in Sundance TV’s Hap and Leonard—a drama based on the Joe R. Lansdale book series focusing on male friendships in America.  

“I think we sometimes forget that many Black people are socially conservative—especially when factoring in religion,” says Moore. “Williams’s Leonard felt like an expansion of what he was already doing in his career: giving voice to lives we often take for granted, and further proving that gay Black men have more layers worth exploring in film and TV.” Williams’s storied career has been a constant testament to that notion. And while losing him on September 6, 2021, remains painful, his body of work and the good it did to broaden people’s perceptions of gay Black men is a legacy that can never be overstated. 

Michael Arceneaux is the New York Times best-selling author of I Can’t Date Jesus: Love, Sex, Family, Race and Other Reasons I’ve Put My Faith in Beyoncé and I Don’t Want to Die Poor. 

*This article appears in the May/June 2022 issue of ESSENCE on stands now.