The 20 most influential TV antiheroes of the last 20 years

“Omar comin’!” Those two words struck fear into every drug dealer working the Baltimore streets in David Simon’s top-down, five-season study of crime, corruption and poverty. As a stick-up man who only targeted drug dealers and their associates, Omar (Michael K. Williams) possessed the most unshakably consistent moral code of any character on the show.

Walter White’s post-cancer diagnosis transformation from high school chemistry teacher to ruthless drug kingpin (turning "Mr. Chips into Scarface ,” as series creator Vince Gilligan famously said) made for one of the most darkly fascinating personal journeys in television history. Gilligan’s writers were fearlessly inventive in their plotting, but it’s impossible to imagine the White’s tragic evolution resonating so deeply with anyone other than the brilliant Bryan Cranston in the role.

A brutal, unapologetically corrupt LAPD detective, Vic Mackey (Michael Chiklis) was the full-throttle force of nature protagonist of Shawn Ryan’s critically acclaimed FX show. Mackey may routinely abuse his power as a member of law enforcement, but he justifies his amoral actions — including murder — by arguing he’s doing everything to protect and provide for his family.

As suavely embodied by Jon Hamm, advertising executive Don Draper may be the most seductively likable serial philanderer in the history of fiction. We learn early on in the series that Draper is himself the fictional creation of Dick Whitman, who stole the identity of a deceased fellow soldier in the Korean War. Ergo, everything Draper does is a clear-eyed choice: the cheating, the emotional abuse, the creative selfishness and, on occasion (particularly in his dealings with Peggy Olson), the tough-love encouragement.

The eloquently profane proprietor of the Gem Saloon is essentially the devil of Deadwood, but for business and industry to flourish in the nascent days of the American West, you need a devil to manage the unsavory capitalistic details. Swearengen often operates in opposition to law enforcement (indulging in murder from time to time), but he is first and foremost a practical man; he welcomes law and order so long as he can play a pivotal role in defining the terms of both.

Westeros is rife with antiheroes. In terms of the most fascinating, it’s probably a toss-up between the Lannister brothers, Tyrion and Jaime; in that case, let’s go with the one who didn’t launch Bran Stark out of a window. Given the prejudice and disrespect engendered by his dwarfish stature, Tyrion’s had to rely on his wits for most of his life. He is a well-practiced schemer, capable of seeing several moves ahead of his adversaries, but his path to power is complicated by his inconvenient conscience.

America’s fascination with serial killers has been massively overexploited via film, television and literature, so it takes a unique hook to stand out from the mass-murderer crowd. For a large chunk of its eight-season run, “Dexter” managed this trick by introducing us to a forensic specialist for the Miami Police Department who moonlights as a vigilante serial killer of serial killers. Even when the series lost its way narratively, Michael C. Hall’s charismatic portrayal of the title character made it difficult to turn away.

Kerry Washington took television by storm as the formidably savvy political fixer Olivia Pope on Shonda Rhimes’s “Scandal.” Washington made it easy to root for Pope throughout the series’ seven seasons, but Rhimes and her writers portrayed her as a morally lax operative forever in danger of being derailed by her overly ambitious nature. Pope could be a ruthless, hardly heroic customer. 

Most of the uproarious misadventures encountered by the crew of the Planet Express have been brought about by this hard-drinking, mad-at-the-world robot. For all his selfish bluster, Bender does have a conscience buried deep in his circuitry, but it generally requires a second party — usually Fry or Leela — to activate it. As a result, he’ll let moral quandaries (e.g. the time he became a god to a species of tiny aliens) spiral well out of control before ultimately, usually doing the right thing.

When Vince Gilligan announced he was spinning off a new series for the scheming attorney from “Breaking Bad,” no one expected he’d wind up crafting one of television’s most emotionally devastating long-form tragedies. Now heading into its fifth season, the story of how a gifted, down-on-his-luck lawyer (Bob Odenkirk) is driven to increasingly nefarious associations keeps surprising, even though we know it all ends at a Cinnabon in Omaha, Nebraska (or does it?).

There are no pure-of-heart heroes in this outrageously entertaining Showtime drama from creators Brian Koppelman and David Levien; all of the main characters are liable to pull a heel turn at any given moment. Though he should be the most despicable person in the series, “Billions” is at its delectably nasty best when the writers have us rooting for Damien Lewis’ cocky hedge fund mastermind Bobby Axelrod.

The mercurial and troubled Slayer, played to pissed-off perfection by Eliza Dushku, veered from hero to bad girl to hero again throughout the combined narratives of “Buffy the Vampire Slayer” and its spinoff “Angel.” Even when she pulled a total heel turn during the third season of “Buffy,” viewers were rooting for Faith to conquer her demons and find her way back to the path of righteousness. Fortunately, the writers realized she was far too interesting a character to relegate to straight villainy.

The would-be criminal kingpin of Harlan, Kentucky, generally served as the antagonist to Timothy Olyphant’s quick-draw U.S. Marshal Raylan Givens, but when far more dangerous outsiders made a play for a piece of the town’s illicit business, Givens and Crowder could briefly find common cause. After a memorable run on “The Shield,” Walton Goggins' portrayal of Crowder was a six-season tour de force.

Josh Holloway’s ruggedly handsome con man became a fast favorite of “Lost” viewers. Though initially positioned as an antagonist to Jack, Sawyer eventually ingratiated himself with his fellow survivors and emerged as the show’s Han Solo. When the writers wised up and romantically paired him with Evangeline Lily’s Kate, their combustible chemistry threatened to throw the entire ensemble's dynamic out of whack.

Considering the twisty, ethically ambiguous doings at Westworld, Ed Harris’ maniacally driven guest, The Man in Black, frequently finds himself playing the role of sadistic villain. Judged on the optics (i.e. the sheer number of hosts he murders and the pleasure he seemingly takes in doing this), he’s anything but sympathetic. But his quest to get at the central mystery of this misbegotten theme park is one of the most compelling arcs in this oft-confounding series.

If the “Eastbound and Down” narrative had been told from a different, decidedly saner perspective, the character of Kenny Powers might very well be its antagonist. Danny McBride cut an indelibly loutish figure as the former Major League Baseball fireballer forced to teach gym class at his former middle school. His victories are often pyrrhic and typically come at the horrible expense of innocent (or less terrible) people. There are glimmers of a decent person in Powers, but they’re easily blurred by his selfish impulses.

It’s difficult to tag Bill Hader’s contract killer, Barry Berkman, as an antihero. Yes, it’s somewhat encouraging that he wants to leave behind his murderous past, but the point of the show thus far isn’t one of redemption or simply, smugly letting Barry off the hook. But we’re helplessly drawn to the character, particularly when he’s juxtaposed with the remarkably lovable acting teacher Gene Cousineau (Henry Winkler).

Joseph Weisberg’s critically acclaimed AMC drama compelled viewers to root for Russian sleeper agents working to bring down the United States government in the 1980s, and this is a testament to the deeply lived-in performances from Keri Russell and Matthew Rhys. It was an impressive six-season balancing act that never took the easy way out by having them betray Mother Russia as a means of redeeming them in the eyes of American audiences.

As the Vice President of the Sons of Anarchy, Jackson “Jax” Teller (Charlie Hunnam) is a violent man in a brutally violent business, but compared to some of his compatriots, he’s practically a boy scout. Shawn Ryan’s biker series took great pains to not prettify its sleazy milieu, and, to that end, Teller definitely does some terrible things (like walking out on his pregnant wife who subsequently overdoses on heroin). But the character is on something resembling a righteous path, which sets him apart in this world.

David Chase’s groundbreaking HBO series hooked viewers with the then-peculiar notion of a hulking mob boss seeking therapy to treat his worsening anxiety disorder. As brought to life by the late, great James Gandolfini, Tony Soprano was, for a time, the most relatable murderer in television history. The longer we hung out with Tony, the less we sympathized with him, but that lingering emotional fragility, and his unswerving loyalty to his family, led us to foolishly believe he could be redeemed. This was never in the cards, but we still enjoyed his company every step of the way.