Despite one being listed at #2 and the other being listed at #1, Joffrey and Ramsay are a tie for the top position on this list, being as equally loathsome as one another. House Bolton exist in the series to prove that not only the Lannisters and their bannermen are bad. They have an uneasy relationship with the Starks, their liege lords in the North, and are renowned for flaying the skin of their enemies. The head of the house, Roose Bolton, is initially depicted as a cold and cunning individual, yet one who is ultimately loyal to Robb Stark, though it is hinted in A Clash of Kings that all may not be as it seems. Ramsay, Rooses bastard son, is introduced in the same book, as dialogue in Winterfell reveals that he has raped and forcibly married the recently widowed Lady Hornwood before leaving her to starve to death in order to obtain her lands. Ser Rodrik Cassel sets out to bring Ramsay to justice for his crime and ostensibly kills him, taking his servant, an unkempt man called Reek, captive in the process and bringing him to Winterfell. Winterfell soon falls to Theon Greyjoy, however, and Reek secures his release by feigning loyalty to its new master. He then becomes one of Theons subordinates and earns his trust by killing two orphan boys to cover the escapes of Bran and Rickon Stark, before leaving the side of his new master to buy men from the Dreadfort (the seat of House Bolton) to ostensibly help prevent the approaching forces of Ser Rodrik from retaking the castle. Reek returns with a host and butchers Ser Rodrik and his men to reiterate his loyalty to Theon, who opens the gates for them. At this point, Reek is revealed to be the one who was killed and the man in front of Theon is in fact Ramsay, who has been toying with the heir to the Iron Islands for his own amusement. He and his men then proceed to murder every remaining citizen and Ironman remaining in the castle in cold blood, taking Theon captive. Ramsay then disappears for two books, though Roose, initially dismissive of his son, turns on Robb Stark, killing him at the Red Wedding and joining with the Lannisters, who reward him by making him the new liege lord of the North. Ramsay is then legitimised as his heir, having murdered Domeric, Rooses legitimate son, several years prior. In A Dance With Dragons, Ramsay's unspeakable crimes continue as he tortures the captive Theon, removing several of his teeth and finger/toe joints and flaying his skin, as well as seemingly castrating him (though this is only implied). He continues to torture others as well, regularly having his men and hounds both rape and kill subjects. This displeases the returning Roose, who nevertheless remains surprisingly nonchalant about the obnoxious exploits of his offspring, bringing Arya Stark (actually Jeyne Poole) back to the north with him to serve as Ramsays bride, allowing them to cement their newfound claim to the Northern region. Developing a penchant for abusing Jeyne and forcing Theon to watch, Ramsay becomes enraged when the two escape, killing all the individuals involved apart from Mance Rayder, who he puts in a cell in the cold with only the flayed skins of his companions for warmth. Now that Winterfell is surrounded by the army of Stannis Baratheon, how much longer Ramsay will live for is unknown, but he will certainly go down in literary history as one of the most despicable characters to ever grace the page.