1. Mickey Doyle, Boardwalk Empire
As far as mob henchmen go, Mickey Doyle is the pits. His jokes fall flat, his work ethic is near nonexistent, and his loyalty for boss Nucky Thompson is constantly in question. He’s been pinched by the feds a number of times for liquor violations, putting Thompson’s operation in danger each time, and, honestly, if U.S. Marshals had offered witness protection in the ’20s, Doyle probably would have sold Nucky up the river 10 times over by the show’s third season. How he’s still alive—especially with his absolutely creepy laugh—is completely inexplicable, and yet, were Thompson to kill him, viewers would probably deride the boss (who’s a little greasy himself) for being a heartless jerk. Some fights, just can’t be won.
2. E.B. Farnum, Deadwood
With his clammy hands, greasy hair, and even greasier attitude, hotel owner E.B. Farnum doesn’t have all that many redeeming qualities. While he’s certainly a go-getter, Deadwood viewers get the feeling that even though he’s pledged loyalty, he’d sell town boss and certified badass Al Swearengen out in a second if the chance arose. Swearengen and his crew—swarthy and sweaty Dan Dority, Johnny Burns, and Silas Adams—certainly don’t like E.B., making it anyone’s guess as to why they haven’t killed and replaced him with a much more capable spy and innkeeper. Who knows, though? It might be that the only reason he’s even alive is that they’ve taken pity on him for being such a simp, what with his terrible diction and predisposition for digestive problems.
3. Uncle Junior, The Sopranos
It’s common knowledge that Sopranos creator David Chase originally planned to knock off Tony’s mother, Livia, at the end of the show’s first season, but when it came time to pull the trigger (or rather, lower the pillow), he couldn’t bear to part with actress Nancy Marchand. But apparently Chase never gave any thought to Tony whacking Corrado “Junior” Soprano, even though it was Uncle Jun who actually ordered the hit on Tony while Livia merely gave her tacit approval. That’s all good for those in the viewing audience, given that Dominic Chianese’s wry performance was one of the series’ ongoing pleasures. Instead, Junior was arrested at the end of the first season and continued to be a thorn in Tony’s side, even while under house arrest and slipping into dementia. Tony’s leniency nearly proved fatal again in the sixth-season première, when his increasingly unbalanced uncle mistook him for an old enemy and shot him in the gut. And yet Uncle Jun made it to the end of the series, surely becoming the only man to take two shots at Tony Soprano and live to tell the tale (if only he could remember it).
4. Benjamin Linus, Lost
He was only supposed to be around for a couple of episodes and was designed to put a face on the still-mysterious Others during the show’s second season, but showrunners Damon Lindelof and Carlton Cuse were so taken with Michael Emerson’s performance that they transformed Ben Linus into one of the program’s central characters. This wily-tongued manipulator was constantly in danger, yet managed to talk his way out of just about any life-threatening situation. Sure, he often found himself beaten to a bloody pulp, yet always had another card to play that ensured his survival. By the end of the series, most survivors of Oceanic 815 grew tired of trying to kill him, and settled for grudgingly appreciating his uncanny ability to avoid death’s grip. Ben couldn’t always take advantage of every situation, but the man could sure take a punch.
5. Paulie Taglia, Crime Story
Michael Mann’s Crime Story was built around an obsessive, running battle between two powerful antagonists: top cop Mike Torello (Dennis Farina) and rising crime boss Ray Luca (Tony Denison). Of all the weapons in Torello’s arsenal, none inflicted more damage on Luca than his own first lieutenant, Paulie Taglia, a stumpy, rubber-faced hood played by former career criminal John Santucci. In their first scene together, Luca was seen whaling on Paulie after one of the sidekick’s many screw-ups; Paulie later tried to make it up to his boss by rescuing him from a shoot-out, only to take him to a safe house that was actually a nuclear test site. The dynamic between the three characters was perfectly summed up in the closing minutes of the second-season finale, which turned out to be the conclusion of the series. Torello and Luca are slugging it out aboard a small private plane, while Paulie is seated next to the pilot. But rather than settle the eternal question of which of the macho men would win in a fistfight, Paulie impulsively shoots the pilot for calling him “dummy,” and the place crashes into the ocean.
6. Vinnie Terranova, Wiseguy
On Wiseguy, federal agent Vinnie Terranova (Ken Wahl) worked deep undercover, serving under a string of mobsters and other ethically questionable types. The show was designed to have rapid turnover in its Big Bads, which made it more believable than if Vinnie’s true identity had gone undetected while he served the same master for several seasons. But it was still a wonder that none of his bosses ever decided to pop him just for being a bad gangster. Any major criminal operation that had his fingerprints on it was sure to crash and burn, and if he had a special talent, it seemed to be his knack for getting arrested. In one early episode, his original boss, Sonny Steelgrave (Ray Sharkey), is seen springing him from jail and joking that he needs to teach Vinnie how “to make an escape.” He’s perfectly good-natured about it, but bailing out the newbie eventually stops being amusing.
7. Alex Krycek, The X-Files
Villains on The X-Files rarely stayed around more than a season (most of them even less), so Alex Krycek’s continued survival was impressive in and of itself. But what makes it even more astonishing is that the character, played by Nicholas Lea, was arguably the most relentless opportunist the series ever had, willing to sell out his current masters at even a hint of a better deal down the line. Introduced in the second season as a temporary FBI partner for Fox Mulder (Scully had been abducted by aliens to cover for Gillian Anderson’s real-life pregnancy), Krycek quickly developed into a crafty, relentless opponent, a free agent in a world of constantly shifting ideologies, whose only real goal was to come out ahead. Given how readily the show’s various cabals dispatched the disobedient, it’s impressive that Krycek was able to stay ahead of the game as long as he did, especially considering the number of times an episode ended with him stuck in a seemingly inescapable death trap. Other characters survive through good luck and/or overly lenient bosses; Krycek seemed to stay running on sheer force of will—until he didn’t.
8. Arvin Sloane, Alias
As much as Alias sat squarely on the shoulders of its lead character, double agent and wig aficionado Sydney Bristow (Jennifer Garner), equally important to the show’s success was its main villain, Ron Rifkin’s ruthless, creepily paternal Arvin Sloane. He orders the killing of Sydney’s fiancé in the first episode, and later blows up her partner’s wife while he and the kids watch. But no matter how many times Syd and her cohorts swore revenge, the show found a way to keep Sloane around, at one point even making him the boss of several of the people who had vowed to kill him several times over.
9. Debra Morgan, Dexter
Dexter has made sort of an open question of whether Dexter will ultimately be forced to kill his adoptive sister and sometimes love interest, but that is sort of assumed in a show where the main character is a serial killer. Ever since Deb learned Dexter was a serial killer in the season-seven première and subsequently spiraled (to the degree that she has now killed a handful of people without necessarily following Dexter’s code), it’s seemed more and more as if the titular character would ultimately have to do her in. After all, the code Dexter lives by includes “don’t get caught” as a “get out of jail free” card if any police officers come snooping around. Yes, Deb is keeping Dexter’s secret, but for how long? And can Dexter possibly guarantee that in a world where she seems increasingly like a loose cannon? It’s about the only thing that passes for ambiguity on TV’s dumbest show anymore.
10. Saul Goodman, Breaking Bad
Breaking Bad’s Saul Goodman knows way too much about way too much to have lasted this long. In fact, the very moment that the character was truly defined—very old spoiler alert—was the moment he could’ve died at Walter’s hands in the season-two episode “Better Call Saul.” If Goodman let himself get into that situation by underestimating Walter, how good can his instincts really be? And if Saul Goodman is as connected to as much dirty dealing as he seems to be, he must be the luckiest lawyer alive—he’s the definition of a loose end. Maybe he’s just got multiple “insurance policies” that haven’t been shown on screen.
11. Clay Morrow, Sons Of Anarchy
Clay Morrow murdered and lied his way to the top of SAMCRO, double-crossing everyone who ever trusted him—and beating the shit out of his loyal wife, to boot. There are half a dozen characters—each capable of murder—who have reason to want him dead, the greatest of whom is Jax Teller. Morrow not only murdered Teller’s dad and married his mom, he also put Jax’s wife and kids in mortal danger. There was a moment when showrunner Kurt Sutter should’ve put Morrow out of his misery, and only a ridiculous plot point (the Irish will only work with Clay!) saved him. Still, his time is probably coming.
12. Wynn Duffy, Justified
Actor Jere Burns—who’s not a bad-looking guy—deserves credit for making the character of Wynn Duffy physically look like a weasel at all times. Maybe it’s the voice, or maybe it’s Duffy’s survival-at-all-costs motivation, but the character manages to irritate everybody around him and make viewers’ skin crawl. Duffy is not just a weasel, he’s a weasel among alpha dogs who’s always trying to play a bigger game than he seems capable of. He’s good at talking himself out of tough situations, which has saved his skin at least once—and he’s also got a dumb, understated bodyguard, Mike, on hand at all times.