Roaring Rampage of Revenge: While he was locked up in Arkham between Seasons 1 and 2, a group of guards liked to beat the crap out of him on a regular basis (not that he didn't deserve it). In Season 2 he's spending his time hunting them down and murdering them one by one.
He Who Fights Monsters: In Season 2, to the point of recruiting Scarecrow to work for him by promising his old job and office back in return.
Trauma Conga Line: First, Arkham is carjacked by the Joker and forced to act as an accomplice to his kidnapping of Bolton. Then he is taken to his house, tied up along with his wife, and told that a bomb will kill her at midnight unless he follows his instructions. Then, after the church incident, he escapes in the middle of shootout between the Joker and Gotham police, only to be captured again after the Joker commandeers a squad car. Then, after being forced to sell the asylum to Lex Luthor, he watches as his house blows up with his wife still inside it. She survives, but is in a vegetative state with little chance of recovery. That in a nutshell is what amounts to his Start of Darkness.
Pragmatic Villainy: Ultimately considers acquiring Arkham Asylum more trouble than it's worth, and agrees to sign it back over to Dr. Arkham. However, Arkham thinks this is merely Lex Luthor Code for "As soon as I get out of here I'm paying a hitman to shoot you in the face", so he has Two-Face shoot Lex in the face instead.
The Casanova: Is apparently able to charm men into bed in extremely short order, usually starting with just a smile. Although, since they are men, this may have more to do with certainothertropes than it does with this one.
Mythology Gag: "I like to keep my involvement with the Wayne family Hush, Hush.