Played By - Roger Cross, Episode - Day 6: 9.00am-10.00am Jack Bauer saw many of his friends die during the original eight seasons of the show, but rarely was he the one to end their lives, usually saving his bullets for the overwhelming volume of adversaries he is pitted against in each episode. One that he did have to kill, however, was Curtis Manning in season six, after working closely with the man, a fellow CTU operative, during the previous two seasons. Following Jack's rescue of renowned yet supposedly reformed terrorist Hamri Al-Assad, Curtis' professionalism is overridden by his personal loathing of the man, who was responsible for the torture and execution of several of Curtis' men during an operation in Iraq. Unwilling to accept that the target of his hatred is set to receive a pardon for the assistance he can provide in tracking down his former lackey Abu Fayed, he goes to kill him, refusing to lower his weapon when Jack commands him to cease. As Curtis fails to relent, Jack regretfully puts a bullet in his neck, killing his ally and prompting him to break into tears a short while afterwards.
5. Edgar Stiles/Lynn McGill
Played By - Louis Lombardi/Sean Astin, Episode - Day 5: 6.00pm-7.00pm/7.00pm-8.00pm The conspiracy that begins with the assassinations of David Palmer and Michelle Dessler and spreads through three seasons to season seven incorporates a series of nerve gas attacks in season five. The target of one of these attacks is CTU, and though several of the people present, including Jack Bauer, his daughter Kim and Chloe O'Brian, are able to seal themselves temporarily in certain areas of the building, others are not. This is exemplified in a highly tragic fashion, as the group are powerless to do anything as they witness the likeable if somewhat pathetic Edgar Stiles emerge in an unprotected area, unsure of what is going on. As he becomes overwhelmed with the horrible symptoms of exposure, he dies painfully in front of them. This death is followed one episode later by a more heroic one, as the detested bureaucrat Lynn McGill opts to redeem himself (being responsible to the attack due to the theft of his access card) by exposing himself to the gas in order to vent it and allow the rest of the people in the building to escape before the gas eats away at the seals and condemns them also.