11. 24 - Season 5 Finale - (6:00 a.m. - 7:00 a.m.)
There has been plenty of heart break for Jack Bauer but the end to his fifth day was one of the worst. What began with the jaw-dropping deaths of David Palmer, Michelle Dessler and - the audience assumed - Tony Almeida, only got worse. After taking down the corrupt US President Logan and stopping the unleashing of nerve gas upon Los Angeles, Jack Bauer found himself captured by Chinese agent Cheng Zhi. Jack never really got to have happy endings but this was one of the worst. He faked his death at the end of season four to avoid the Chinese but by returning to the fold and becoming a hero once again, he found himself on the Cheng Zhi's radar and this time he couldn't escape his fate. Smuggled out of the country - and subsequently tortured for two years - this was one of the most shocking, bleakest cliffhangers in the show's history. Of course, it all happened again with the Russians in the closing moments of season nine's Live Another Day, proving once and for all that Jack Bauer is the unlikeliest man on the planet.