Original Gangster: A Side-by-Side Comparison of Omar Little and Chalky White

Image via Complex Original

Chalky White: Though our introduction to Chalky comes via his illicit dealings in the crime-filled landscape of 1920s Atlantic City, in the fourth-ever episode of Boardwalk Empire we learn a bit about native Texan Chalky’s past in an amazing scene in which Chalky tells a story about his father—a talented self-taught carpenter—who was hanged by a half-dozen men simply for being black. It’s implied that Chalky, who would have been a child at the time, witnessed the brutal execution, and as such led him down the criminal path.

Omar Little: Unlike many of his gun-wielding colleagues, Omar Little was not born bad. But he did grow up in a family, and in a city where crime is simply a way of life. Shortly before The Wire’s fifth season premiere, HBO created a series of character prequels, one featuring a very young Omar who is recruited by his older brother Anthony (a.k.a. No Heart Anthony) to rob a man in 1985. Omar’s legendary moral compass is already well established, leading his accomplices to determine that he’s not cut out for the criminal lifestyle.

Chalky White: Many of Boardwalk Empire’s characters are based (at least partially) on real-life people, and Chalky White is one of them. Except unlike Nucky Thompson (who is the televised version of Nucky Johnson), Chalky was based on Chalky Wright, who was a boxer, not a gangster. “He was a boxer from the West Coast,” Williams explained during an HBO Q&A. “Although Chalky from Boardwalk Empire isn’t a boxer, but what it took for him in those days—fighting all the white boxers and dealing with all the racism in the sport—I took that and infused it into Chalky White the character.”

Omar Little: Though real-life Baltimore stick-up man Donnie Andrews, who passed away in 2012, is the most frequently cited inspiration for Omar’s character, The Wire creator David Simon has mentioned a number of other local criminals—including Shorty Boyd, Ferdinand Harvin, Billy Outlaw, and Anthony Hollie—as other real-life personalities who share traits in common with Omar.

Chalky White: Though Chalky’s eye begins to wander as the series progresses and family relationships change, our introduction to him is as a family man—husband to a well-educated wife, Lenore, and father to three kids, Lester, Maybelle, and Adeline.

Omar Little: Though he was orphaned as a child, Omar was raised by his beloved, god-fearing grandmother, Josephine, whom he regularly accompanies to Sunday church service. As for his love life, that’s one aspect of Omar that makes him so unique in the tough-guy circles in which he runs: He is a proud gay man who maintains close and loving relationships with a few different partners throughout the series’ run.

Chalky White: Though Chalky tends to put business first, or at least put up that front, he can be shrewd—and cruel—when the situation calls for it. But at his heart, he is a man who acts out of responsibility and loyalty to his loved ones, and as such is guided somewhat by a self-defined moral compass.

Omar Little: It’s hard to mention Omar’s name—or read anything about his character—without hearing/seeing the phrase “moral compass.” Though he’s not averse to robbery or even murder, Omar’s most defining characteristic is that he only sets his criminal sights on bad guys. (He also abhors profanity.) Like West Baltimore’s own robbery-prone Robin Hood, Omar lives (and dies) by his own rules of righteousness.

Chalky White: As one of Atlantic City’s most prominent (and prosperous) black businessmen, Chalky White stands as the unofficial leader of the city’s African-American community. He’s an ally to the most powerful white politicians, as he has the ability to buy them the black votes when needed (for a sum). And he has the undying support of his fellow citizens because he isn’t afraid to share the wealth and step in as a mediator when racial tensions arise within the city.

Omar Little: Omar, too, is a bit of a legend in his neighborhood—mostly because he is a fearless fighter and a cunning stick-up man. When you see Omar coming, you know something’s about to go down, which is why you’ll hear neighborhood residents young and old yell out that “Omar Comin’” whenever he—with his trusty trench coat and shotgun—walks down the street.

Chalky White: Perfectly-tailored suits were the basic uniform of Atlantic City’s most powerful players (and bootleggers), and Chalky’s sartorial choices were some of the most impressive of them all. With a penchant for three-piece suits and subtle plaid prints, Chalky’s look was never complete without his ever-present bow tie.

Omar Little: With the exception of Brother Mouzone, you’d be hard-pressed to find anyone wearing a bow tie on the streets of West Baltimore (and live to tell about it). But Omar, too, has his own street style-inspired outfit of choice: it’s casual at its most basic level, as in jeans and a sweatshirt. And it is topped off with the most important (and iconic) elements: a bulletproof vest (smart) and a dark brown duster that’s big enough to conceal his favorite accessory—a shotgun!

Chalky White: Bootlegging isn’t Chalky’s only business venture; he’s also a nightclub owner with an ear and eye for, and love of, music.

Omar Little: In the second season of The Wire, while waiting to be called to the witness stand, Omar assists the bailiff with a tricky crossword puzzle clue asking for the Greek God of war. The answer, Omar tells him, is Ares. He admits that he’s long been fascinated by Greek mythology.

Chalky White: Chalky has expended a lot of time and energy in building up his brand, and when it comes to the Machiavellian question of whether it’s better to be loved or feared, he leans firmly to the latter. Case in point: Dunn Purnsley, Chalky’s jail cell antagonist-turned-dedicated henchman.

Omar Little: Omar’s crew is small and tight-knit, and it operates like an honest to goodness family (that happens to hold up drug dealers on a regular basis).

Chalky White: Like many great television gangsters before him, Chalky White’s many criminal wheelings and dealings eventually caught up to him by the end of the series. Chalky lived life loudly, and he certainly didn’t go out with a whimper—it took a full firing squad to take Chalky down.

Omar Little: Though Chalky’s passing was a tragic one, Omar’s demise came in the most ironic of ways: While making a quick stop at the bodega around the corner, he is shot by an innocent-looking young boy—just the kind of kid he dedicated his life to protecting.

Chalky White: Though Boardwalk Empire never shied away from killing off even its most beloved characters (see: Richard Harrow, Jimmy Darmody, and Owen Sleater), Chalky’s death was still one of the hardest for fans of the show.

Omar Little: Like Chalky, Omar’s many fans mourned his passing on the show. But Omar was able to one-up (well, two-up) Chalky in the fan department. In 2008, then-senator Barack Obama told the Las Vegas Sun that The Wire is his favorite TV show and that Omar is his favorite character. (Top that, Chalky!)