Advance Wars: Dual Strike - multiple times due to medal requirements
Atelier Rorona: The Alchemist of Arland - 2, though had to load a save file near the end multiple times to see all the endings
Atelier Totori: The Adventurer of Arland - 2, see above
Disgaea DS - 2 for the actual end, more if you include other endings
Earthbound - 2
Final Fantasy IV - 2, GBA and PSP
Phoenix Wright: Ace Attorney - 3
Phoenix Wright: Ace Attorney Justice for All - 3
Phoenix Wright: Ace Attorney Trials and Tribulations - 3
Shin Megami Tensei: Devil Survivor - at least 12 times for both itself and its remake to get all endings
Tales of Symphonia - 3
Time Hollow - 2
That's all I can think of right now. At the moment going through a second play through of Fate/Extra.
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Congrats to 2011 Rivalry Rumble Guru winner, SuperNiceDog
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