The Wire's Michael Kevin Darnall and Michael K. Williams

Gay characters haven’t had a visibility problem in pop culture in years. But when it comes to minority representation, quality is more important than quantity, and there was a time when most gay male characters were portrayed as stereotypically effeminate nellies. If they weren’t obsessively coordinating weddings, they were investing themselves in their girlfriends’ rom-com drama, as if they didn’t have problems or love interests of their own. As gay men have become more visible, so has the idea that gay men come in all shades of humanity, including the darker shades most often associated with heterosexuality. Pop culture has gradually figured out that gay guys can be brutal badasses, and that a bullet to the back of the head is no less deadly if the shooter checks out your butt first.

1. Omar Little, The Wire

The denizens of The Wire’s Baltimore projects have a deep phobia around infamous stick-up man Omar Little (Michael K. Williams), but it isn’t homophobia. It’s a perfectly reasonable fear of an outlaw who totes around his double-barreled shotgun as conspicuously as possible, and has a proven track record of unloading it on anyone who crosses him. Omar is introduced alongside his boyfriend Brandon (Michael Kevin Darnall), though you’d never know their relationship status since they’re first seen planning to rob the Barksdale drug syndicate. In the following episode, after they execute the hit, a contrite Brandon beats himself up over identifying Omar by name during the robbery. Omar is characteristically unruffled. “I don’t really care you shouted me out,” he says. “Everybody in these projects been knowing Omar, you heard? I just don’t want them coming down on y’all, baby boy.” Omar puts his arm around Brandon and pulls him into a loving embrace, and their partner-in-crime John Bailey (Lance Williams) looks on with slight bemusement. Omar implies his interest in John too, but John politely rebuffs him and shuffles away. John doesn’t look horrified or disgusted by the intimate exchange, more like he keeps forgetting that Omar and Brandon are lovers and he’s the third wheel. [Joshua Alston]

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2. Vito Spatafore, The Sopranos

The code of masculinity among the gangsters of The Sopranos is as old world as the cuisine at Nuovo Vesuvio. The men in this world are expected to be breadwinners, to protect and intimidate through extreme violence, and to sleep exclusively with women. Even the slightest deviation from these roles reflects poorly on a man and his family (both types)—hence Tony Soprano’s initial secrecy about being in therapy, or the entire cast’s less-than-enlightened views on homosexuality. By the time mob capo Vito Spatafore is caught giving an early morning blowjob to a security guard, there are five seasons full of gay slurs telegraphing what comes next. After running into some associates who are shaking down a leather bar, Vito flees to New Hampshire, a self-imposed exile that nonetheless injects some hope into the show’s bleak final season. In Vito’s romance with a short-order cook, The Sopranos hints at a new form of escape for its insecure wise guys: They needn’t die, or betray their family—they could just try living a life that isn’t dictated by ancient Sicilian bullshit. That bullshit eventually catches up to Vito, but his fate serves as a powerful push against the gangsters’ code. Who he loves is not a choice, but joining the Mafia was, and it’s the latter that seals his doom. [Erik Adams]

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3. Sam Adama, Caprica

Given Battlestar Galactica’s preference for exploring its characters’ homosexuality exclusively in the off-season, in TV movies and webisodes, there’s no reason to expect its prequel series to expand the tent. And it doesn’t immediately. At first Sam Adama (Sasha Roiz) is just a defendant in a criminal case, a known member of a crime syndicate, the D’Angelo Barksdale of Caprica. By the end of the two-hour pilot, he shows us what a mob enforcer does exactly. He sneaks into his target’s house at night—shirtless, the better to display his beefy bod and the two daggers sticking out of his pants—wakes the guy up so he knows it’s coming, and then brutally slashes him to death. In later episodes come the twist: This macho badass dates men! Well, he dated men—well, he tried to date men—he tells his nephew on a walk. It’s a fly-by line, a testament to queer normalization in this universe, but in the next episode, it’s impossible to miss: Sam goes home to his concerned husband Larry (Julius Chapple). Try as Larry might, he and Sam don’t have nearly the intimacy of Sam and his murder victim. What couple could? [Brandon Nowalk]

4. Teddy Bass, Sexy Beast

A former mobster who’s given up crime for a life of sunbaked luxury, Gary “Gal” Dove has no interest in revisiting his dangerous past. So when the terrifying Don Logan (Ben Kingsley in an Oscar-nominated performance) shows up at his door to recruit him for a London bank heist, there’s already plenty of dread surrounding the crime. Adding to the already Pinter-thick tension is Teddy Bass (Ian McShane), the crime lord who’s organized the caper. McShane’s made a career of playing characters whose testosterone and sociopathy levels are so high, they threaten to poison everyone around them, and Bass is no different. Instead of using the reveal of his sexuality to convey sensitivity, the film simply makes him more brutal and calculating. As Teddy allows the bank chairman to take him from behind so he can get information on the vault, the camera holds on McShane’s sweaty face, his teeth clenched and his eyes bugging out while the wheels turn in his head. Sure enough, he shoots the chairman in cold blood once the heist is over, shattering any illusions of tenderness or even genuinely reciprocated lust. McShane put it more bluntly in a 2010 interview with Out Magazine: “Teddy would do it with a frog if it stopped hopping long enough.” [Dan Caffrey]

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5 & 6. Fante and Mingo, The Big Combo

Having made the subversive, psychosexual Gun Crazy, B-movie virtuoso Joseph H. Lewis upped the ante a few years later by sneaking a gay couple into his noir masterpiece The Big Combo. To modern viewers, violent mob thugs Fante (reedy-voiced man’s man Lee Van Cleef) and Mingo (cop and cowboy character actor Earl Holliman) are clearly more than just partners-in-crime, which is largely a credit to both actors’ performances and to Lewis’ unusually sensitive direction. Introduced as sadistic heavies, the two are tacitly (this was 1955, after all) revealed to be running from something more than just the law. In one of Lewis’ signature long takes, Fante and Mingo talk about their plans for life on the lam (“When we get out, let’s never come back…”) while hiding out from the cops. The relationship comes through in the laidback intimacy between both characters—made all the more complex by the glance Fante throws when Mingo touches his arm—and through inflection. In the space of a single protracted shot, The Big Combo manages to not only give two seemingly irredeemable bad guys a complicated emotional life—it makes them sympathetic. [Ignatiy Vishnevetsky]

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7. Unnamed IRA Hitman, The Long Good Friday

Bob Hoskins’ Harold is the head of London’s gangster underworld in 1980’s The Long Good Friday. The movie is about his very bad holiday caused by Colin (Paul Freeman), his friend and henchman. Colin is first seen pocketing some money that belongs to the IRA, setting off a series of events that includes, but does not conclude with, Colin’s death. The instrument of Colin’s demise is a very young Pierce Brosnan in a tight black bathing suit, successfully cruising Colin at a pool. But as soon as Colin goes in for the embrace, Brosnan’s unnamed IRA hitman stabs him and leaves him for dead. Colin’s homosexuality is never played in contrast to his life as a gangster. It’s his downfall, but his fate would be no different if he was being seduced by a hit woman instead. [Molly Eichel]

8. Bill Rawls, The Wire

The Wire doesn’t usually quite go so far as to say that its cops are just another gang in Baltimore, but it does say that gang violence and drugs are the fault of systemic issues in both government and the police. The avatar of those systemic issues, especially early, is Major Bill Rawls. He’s petty, profane, over-masculine, and cruel; he’s only shown caring about the numbers and never about actually making the city a better place. His most sympathetic moment for nearly three seasons comes when he calls the show’s ostensible hero a “gaping asshole.” So it’s both a quick chuckle and deeply humanizing when the show takes a moment for a scene in a gay bar to show the (married with children) officer Rawls. For a lesser story, this would only have been a joke, but John Doman’s exceptional portrayal combines with The Wire’s depth to make this a revelation about how this three-dimensional character may have become who he became. [Rowan Kaiser]

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9. Felipe Lobos, Power

Pop culture’s ultra-macho, violent gays are often strong, silent types, as if they’re afraid they might accidentally out themselves if they’re too expressive. Kudos to Starz’ Power for creating Felipe Lobos (Enrique Murciano), a ruthless drug wholesaler whose larger-than-life personality would set off alarms for anyone curious about his sexuality. But when you’re as quick on the trigger as Lobos, there’s no need to fear backlash. In the show’s first season, Lobos is limited to brief, infrequent appearances during which he comes across vaguely eccentric more than anything. He becomes a more central character in season two, which at one point finds him relaxing in a luxurious grotto, as kingpins are wont to do, and receiving fellatio from a man. The reveal is milked for shock value, but once it’s out, Lobos’ sexuality doesn’t define the character. Even when he orders a Shirley Temple later in the episode, it just seems like that’s what he’s got a taste for. Lobos walks a fine line: He’s not flamboyantly gay; he’s flamboyant and gay. [Joshua Alston]

10. Paul Smecker, The Boondock Saints

“Masculine” probably isn’t the first word FBI agent Paul Smecker’s colleagues would use to describe him, yet he’s clearly the biggest alpha male in a movie filled with them. Played with a permanent, condescending scowl by Willem Dafoe, he’s first introduced putting a hapless detective in his place at a murder scene, introducing himself by flashing his badge and saying “that’s who the fuck I am,” and he spends much of the movie cutting down his intellectual inferiors. By the time he’s shown in bed with a younger man, it’s less of a reveal than a confirmation—we’ve already seen him reconstruct a crime scene while dancing to opera, after all. Smecker treats his one-night stand with the same brusqueness as he treats all his underlings, swatting him away and calling him a fag when he dares to try cuddling with him. There’s nothing sensitive or subtle about Boondock Saints’ portrayal of homosexuality, but there’s nothing sensitive or subtle about Boondock Saints, period. So when Smecker spends the film’s climax gunning down gangsters while dressed in drag, it’s supposed to be a sign of character growth. Smecker has come to terms with who he is: a gay man, yes, but first and foremost an agent of violent vigilante justice. [Evan Rytlewski]

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11. Sonny Wortzik, Dog Day Afternoon

Although John Wojtowicz (the real-life inspiration behind Dog Day Afternoon) has cited several inaccuracies in the film, the Oscar-winning script actually portrays him with a great deal of sympathy, at least for 1975. For one, there’s his charisma, elevated to crowd-rousing heights by Al Pacino. Two, when his sexuality gets revealed halfway through the film, it’s done matter-of-factly, with little ridicule over the fact that he’s committing a bank robbery so he can pay for his transsexual wife (Chris Sarandon) to get gender-reassignment surgery. Sonny may not be as intimidating or violent as other characters on this list (he’s somewhat of an imbecile when it comes to crime), but that makes him all the more atypical. He’s not depicted as a lowlife or pervert—just a petty thief who’s heartbreakingly desperate. [Dan Caffrey]

12. Eddie Dane, Miller’s Crossing

We meet immense mob enforcer Eddie “The Dane” (J.E. Freeman) in the first scene of the Coen brothers’ noir romp Miller’s Crossing. When The Dane’s boss, Johnny Caspar, says he wants the head of bookie Bernie Bernbaum (John Turturro) for screwing up the odds on some fixed fights, Leo O’Bannon (Albert Finney) suggests the fault may lie with another bookie, Mink Larouie (Steve Buscemi). Caspar disagrees, saying, “Mink is Eddie Dane’s boy.” Leo jabs, “Of course, The Dane always knows about the fix,” adding, “a lot of people know.” The subtext here is that The Dane and Mink are lovers and that it’s not exactly a secret, a notion the Coens—like their characters—only hint at for the majority of the movie. The script is similarly demure about a second gay relationship between Mink and Bernbaum. Tom Reagan (Gabriel Byrne) tells Mink, “If The Dane finds out you’ve got another amigo, well, I don’t peg him for the understanding type.” The film only speaks blatantly about The Dane’s homosexuality once, later in the story when he emerges as Reagan’s chief adversary and the kind of guy who beats up his own muscle to make a point. Reagan suggests that “love” is the reason The Dane would betray Caspar to save Mink. Caspar acknowledges the relationship, but only by repeating, “I know Mink is The Dane’s boy.” It’s clear that mobsters avoid discussing The Dane’s sexuality not to be coy, but to avoid crossing the scariest guy in the business. [Matt Wayt]

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13. Winston Baldry, The Mexican

As gay hitman Winston Baldry in The Mexican—Gore Verbinski’s curious romantic comedy from 2001—James Gandolfini isn’t conflicted about his sexuality. He’s conflicted for the same reason his more famous role of Tony Soprano is conflicted: his deep well of emotions doesn’t always benefit his job title and vice versa. Still, that doesn’t keep him from becoming a confidant to the erratic Samantha (Julia Roberts) after kidnapping her. But even when offering romantic advice on her troubled relationship with Jerry (Brad Pitt), he never loses his brooding edge, the sense that he could easily put a bullet in her head during one of their cozy chats. J.H. Wyman’s script—flat and convoluted whenever Gandolfini isn’t in it—goes as far to directly reference how different Winston is from the gay stereotypes usually seen on the silver screen. When Samantha infers that being homosexual can’t be conducive to being a hitman, Winston growls back at her: “What does my sexual orientation have to do with anything you’re talking about?” Amen to that. [Dan Caffrey]

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14. Matt Wozniak, Shades Of Blue

In NBC’s cop drama Shades Of Blue, Ray Liotta plays a crooked, homicidal cop as only he can. Liotta’s history of playing gangsters and psychopaths factors into the scandalized response to the third episode, in which his character, Lt. Matt Wozniak, abruptly starts making out with Donnie (Michael Esper), his department’s chief of internal affairs. It’s heavily implied that the two have sex, in case anyone thinks it’s just a creative way of breaking the conversational tension. Wozniak is actually bisexual, according to creator Adi Hasak, who insists Wozniak isn’t just using his wife Linda (Lolita Davidovich) as a beard. But considering the high degree of machismo and homophobia within police culture, it’s doubtful any of Wozniak’s colleagues would consider that a significant distinction. [Joshua Alston]

15. Ronnie Kray, Legend

In last year’s Legend, Tom Hardy did double duty as two halves of London’s infamous Kray crime empire, embodying both slick, short-tempered playboy Reggie and his certifiably insane twin brother Ronnie. The latter proves to be the more interesting of these real-life gangster brothers: Convinced of the importance of embracing who you really are, Ronnie makes no attempt to hide his illegal activities—nor, for that matter, his preference for men, which the film treats as matter-of-factly as he does. Being openly gay was brave in the 1960s, but Legend makes the case that that the Kray brothers were so widely feared—for their influence and their brutality—that all of London had no choice but to accept it, even as Ronnie hit the nightlife with hunks on both arms. With Hardy in the (dual) role, summoning that mumbling intensity that’s become one of the Bronson star’s signatures, Ronnie is both fearsome and oddly endearing: A man committed to being himself, without shame or regret, whether that means inviting prominent politicians to his all-male orgies or settling any dispute with vicious violence. [A.A. Dowd]

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16. Francisco Flores, Traffic

They say the way to a man’s heart is through his stomach, but the way to his secrets is through his penis. That’s why spy fiction so frequently relies on men losing their faculties when given or promised sex, but the proposition is usually made by a coquettish woman. That approach wouldn’t have worked on Francisco “Frankie Flowers” Flores (Clifton Collins Jr.), a hitman for the notoriously violent Tijuana drug cartel in Steven Soderbergh’s Traffic. Frankie Flowers prefers the company of men, so Javier Rodriguez (Benicio Del Toro, in an Oscar-winning performance) steps in as the irresistible bait, locking eyes with Frankie in a Mexican gay bar and offering to light his cigarette. Frankie winds up being kidnapped and tortured for details about his employer, which is horrible, but no one can argue he was treated differently because he’s gay. [Joshua Alston]

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17. Andrew Larrick, The Americans

Being gay often becomes a liability in macho criminal, law enforcement, or military settings, where masculinity is both highly revered and incredibly fragile, and any deviation from cartoonish machismo is viewed as a fatal weakness. In the second season of The Americans, KGB sleeper agents Philip and Elizabeth Jennings (Matthew Rhys and Keri Russell) turn this to their advantage, blackmailing naval officer Andrew Larrick (Lee Tergesen) into becoming an informant, lest they expose him as a gay man. Andrew initially acquiesces, but the rage bubbles up inside him. He’s furious at the Soviets for killing his friends in battle, and for dangling his sexuality like a guillotine over his head. He goes from being Philip and Elizabeth’s puppet to their most terrifying adversary, methodically stalking them in a quest for vengeance and leaving several dead bodies in his wake. [Joshua Alston]

18. Robert Quarles, Justified

As the big bad of Justified‘s third season, Robert Quarles (Neal McDonough) was presented as a tonal opposite to the show’s prior low-class gangsters. Between his three-piece suit, Dale Cooper-esque appreciation of the Harlan County climate, and ever-present grin, Quarles appeared totally in control of himself and ready to conduct business. Yet as his plans started to fall apart in the face of Raylan Givens (Timothy Olyphant) and Boyd Crowder (Walton Goggins), an ugliness started to seep through his bonhomie. Gradual digging revealed that he was less supported by the Detroit mafia than exiled by them, his various stories of family life turned out to be a cover for some darker urges involving male prostitutes. Those urges followed him all the way to Harlan, culminating in “Guy Walks Into A Bar” when a young man tracked Quarles down demanding answers on a missing friend—and ending with that young man tied up in Quarles’ bathroom. Heightening the horror of the scene, Quarles continued to hang his suit up, still more committed to the facade than the ugly reality. [Les Chappell]

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