50. Sniper Wolf - Metal Gear Solid
An incredibly skilled sharpshooter who has a love for wolves and dogs, which prompted Otacon to fall in love with her. She provided one of the best moments of Metal Gear Solid when, after she wounds Meryl, Snake confronts her in a sniper battle in the snow, and upon her death she shows regret at having joined Liquid's plot, calling herself a dog, before Snake assures her she was a wild, untamed, wolf.
49. Vladimir Makarov - Call Of Duty: Modern Warfare 2
Makarov is the chief antagonist of Modern Warfare 3, yet the moment that earns him his place on this list is the controversial airport mission of Modern Warfare 2. Believing that you are infiltrating Makarov's group, you join him and his men as you perform a massacre at an extremely busy airport. The scene is actually brutal and harrowing, lending you a great hatred towards Makarov and his plans.
48. LeChuck - Monkey Island
An undead pirate who was known for his cruelty and sadism, LeChuck became undead after finding the treasure of Big Whoop and willingly dooming his own soul for eternity, in exchange for demonic powers. His main goal was to make Elaine Marley, with whom he had an unhealthy obsession, his wife, as well as assuming complete control of the seas by obtaining ultimate voodoo powers.
47. The Creeper - The Suffering: Ties That Bind
During his life the Creeper was an infamous pimp who sated his murderous appetite by killing 50 - 200 women. He appears as a grotesque, overweight man in a large trenchcoat, behind which are the corpses of several women, connected to Creeper by bladed tentacles that protrude from their mouths. His is a horrific villain due to his claim that 'Blood is the best lubricant', an infamously disgusting line.
46. Officer Frank Tenpenny - Grand Theft Auto: San Andreas
Officer Tenpenny is the policeman at the head of C.R.A.S.H, an anti-gang unit in San Andreas. However, Tenpenny is also incredibly corrupt and regularly skims money from each rival gang, as well as killing anyone who gets in his way with the power of the law behind him. Tenpenny regularly convinces good cops to help his cause and believes that some crime must be overlooked for the greater good.