Okay, this thread has been burning a hole in my brain ever since I read it. Tim was my gateway character from casual comic book fan to I must own and read everything. I probably own and read 90% of his starring or co-starring comic book appearances. I actually have a Word document full of all this info, but I’m not sure where I placed it, so I’ll do it from memory and Googling. I’ll try to separate the reason I recommend the story from the issues to avoid spoilers in case you care.
Batman 408-409 (Origin of Jason Todd)
Batman 410-411 (Relationship of Robins to Two-Face)
Death in the Family (Death of Jason Todd)
Batman Year 3 (Technically First Appearance of Tim Drake though just a cameo. Also sets stage for Dick and Bruce’s relationship at the time)
Lonely Place of Dying MUST READ (Tim’s first real appearance and crucial story line)
Detective 608-609 (Introduction of Anarky, one of Tim’s main villains)
Detective 618-621 MUST READ (Death of Tim’s mother and severe injury of Tim’s father)
Batman 455-457 MUST READ (Tim earns the right to be Robin)
Robin (1st Miniseries) MUST READ (Tim’s first solo adventure where he learns what kind of hero he wants to be and meets recurring villains King Snake and Ghost Dragons)
Batman 465 (Tim’s First Adventure as part of the Dynamic Duo)
Batman 467-469 (Rematch against King Snake and Ghost Dragons
Robin II: Joker’s Wild MUST READ (Tim’s first encounter against the villain that killed the last Robin)
Batman 480 (Tim’s Father released from hospital)
Detective 647-649 MUST READ (First Appearance of frequent ally and girlfriend, Spoiler)
Batman 654-654 (First Appearance of Robin villain, The General)
Robin III: Cry of the Huntress (Tim meets ally, the Huntress)
Knightfall (The whole series is a classic, but if you don’t want to read the whole thing, you could start at Detective 496 and work to the end. You’ll get the crucial bits. Find a reading order online because Knightfall crosses over between Batman and Detective Comics. (Batman is broken and Jean-Paul Valley takes the mantle which deeply affects Tim and sets up for Tim’s solo series)
I haven’t even reached Tim’s first ongoing series and I’ve already spent way too long on this. I’ll come back to it later. Suppose I need to get my complete list and create a thread for this.