I messed-up with the title but compensated with the tags. This is actually a reading order for the very beginnings of Batman and family. In short, it's a must collection.
Batman Origins
Legends of the Dark Knight #1
Batman Year One or Batman #404-407
Legends of the Dark Knight #2-5
Dark Moon Rising: Batman and the Monster Men #1-6
Dark Moon Rising: Batman and the Mad Monk #1-6
The Man who Laughs
Legends of the Dark Knight #11-15
Four of a Kind
Legends of the Dark Knight #6-10
Legends of the Dark Knight #16-20
Legends of the Dark Knight #65-68
The Long Halloween
Turning Points #1
Legends of the Dark Knight #21-23
Batman Confidential #1-5
Dark Victory
The Robins, Barbara Gordon and Harold (Mr. Fixxit)
Batman Chronicles: The Gauntlet
Turning Points #2
Batgirl and Robin Year One
Nightwing #101-106 [Dick becomes Nightwing]
Batman #408-410 [Jason Todd Year One]
Batman #416 [Nightwing briefly returns and dons Jason his Robin suit]
A Death in the Family #426-429 [Jason Todd tragedy]
Batman #436-439 [Tim Drake Year One]
The Killing Joke
Batman Chronicles #5 [Oracle Year One]
Batman and Son [Damian Year One]
Batman #458 [Harold]
Resurrection of Jason Todd
Teen Titans Volume 3 #16 (2004)
Batman #608-619 [Hush Story Arc] [Foreshadowing Only]
Batman Annual #25
Red Hood: The Lost Days #1-6
Batman #635-650