7. Batman Fails To Save Jack Drake
2004's Identity Crisis gets a lot of criticism, almost all of which is absolutely deserved. There is one moment in it however that manages to tug on the heartstrings, shedding some of its more problematic elements.
One of the running plotlines is the relationship between Tim Drake (the third Robin) and his father Jack. This plotline comes to a head in the fifth issue when Captain Boomerang shows up at Jack's house. Jack is able to call Tim, and as they talk Tim begs Batman to save his father. Unfortunately, they don't make it in time, and both Captain Boomerang and Jack end up dead in Tim's kitchen.
What makes this sequence truly heartbreaking is how much you can visibly see it affecting Batman. He knows this feeling all too well, and sees it as yet another failure on his part.