Ramsay Bolton (Iwan Rheon) — Games of Thrones
“If you think this has a happy ending, you haven’t been paying attention” were the words spoken by Ramsay Bolton as he took great pleasure in torturing Theon Greyjoy (Alfie Allen); breaking him down, rendering his victim to the state of a submissive dog, and renaming him Reek, forever in his trap. Ramsay, the bastard son of Roose Bolton, fooled us with his boyish looks, mesmerized us with his sadistic nature, and made us consider the depth of darkness that some humans are capable of thriving in.
Gustavo Fring (Giancarlo Esposito) — Breaking Bad
As composed, softly spoken and calm as one could be, Gustavo, also known as ‘Chicken Man’, was one of the most notorious crime bosses in TV history. Seemingly a respectable, decent citizen, his outward demeanor gave little hint of the violence Gus was capable of dealing out. But in fact, he was among the most ruthless villains ever seen on screen, and avenged the loss of his brother, including wiping out his rival’s entire family and committing acts of atrocious brutality, while hardly breaking a sweat.
Negan Smith (Jeffrey Dean Morgan) — The Walking Dead
“Anybody moves, anybody says anything, cut the other boy’s eye out and feed it to his father.” Brutal yet nonchalant and somehow charming, this black leather-clad baddie entranced us with his psychopathic nature, whistling as he went, devoid of empathy, capable of anything in pursuit of his goal. Notorious for his cruel actions, and eloquent and piercing in his monologues, Negan keeps us on the edge of our seats, drawn like a fly to demonic light, captivated by the extent of how far he’s willing to go.
Livia Soprano (Nancy Marchand) — The Sopranos
While Tony Soprano was perhaps this century’s first truly great TV antihero, setting the stage for many wonderful characters to follow, the real villain of the HBO classic was his mom. Livia tried to kill her own son as revenge when he decided to put her in a care home, while her constant narcissism and pessimism sucked the life out of all those around her. “If you want my advice, Anthony, don’t expect happiness,” she once told her grandson. “What makes you think you’re so special?” Actress Nancy Marchand’s role in the show was cut short by her death in 2000, but the writers ensured the character would continue to haunt Tony for many years to follow.
Ben Linus (Michael Emerson) — Lost
Possessing the looks and manner of an everyman, one could be forgiven for thinking that Oceanic Airlines flight passenger Henry Gale, AKA Ben Linus, could be capable of such heinous acts of violence, speaking untruths with quiet confidence, and donning the thorny crown as a master of manipulation. Hailing from the woods outside Portland, Oregon, and moving to the island with his father after his mother died while giving birth, as leader of ‘The Others’, Ben would grow to become the island’s greatest protector and its bona fide bad guy. Inspired to preserve his island at any costs, this unassuming sociopath would sacrifice his own daughter and murder his father to achieve his goals.