5. No Mans Land
The Joker has taken a lot from Commissioner Gordon. He has tried to drive him insane, paralyzed his niece (at the time) and has endlessly threatened the city he is sworn to protect. Yet, perhaps the cruelest blow was yet to come in the terrible dance between the Joker and Jim Gordon. With Gotham paralyzed after an horrendous earthquake, Joker had carved a path of terror through the ruins with his gang, shooting innocents and nearly ending the life of Huntress. Yet the most cruel of blows came when, trying to defend an abandoned group of innocent babies, the Joker did what he always does best and ended the life of Jims wife, Sarah with a bullet to her head. The tragic part is that this is probably not the end of Jokers torment upon the Commissioner.