Thought something like this would be useful and since I'm re-reading through the 160-300 Tim Drake issues I might as well write it up. This is not complete. I will add more to it later, as I go through the books. If you have any suggestions, questions or comments, post it ^.^
When you see a ">>>" it means that this set of events happens within the same space of time as an arc listed above it.
For those Stephanie Brown fans out there, bare in mind this is a Tim Drake guide, but Stephanie Brown more or less begins to co-star starting at around Robin #40. She is an important part of Tim's story and as such so is her story. Most if not all of Stephanie's important appearances can be found within this guide... and those that are likely not to be should be in the Stephanie as Robin issues in Batman and 'Tec, and her other appearances should be easily found by reading through Batgirl vol 1-3. I'm pretty sure the only other appearances she has are in Birds of Prey (maybe) and Batman, Inc. (maybe for like 2 issues)
There are some issues which are bad in my opinion, such as just about anything with the General, but the General plays an important role down the line so I suggest reading a few of those arcs even though I think they're not all that great.
When I mention a story arc by name it generally means I think you should read that entire story arc. I mention this because some stories have prologues, epilogues, and spin offs. Those should all be read in my opinion as part of the arc. This is important because not every arc has been collected completely, like No Man's Land. It roughly spans the entire year of 2000 in at least 6 series, Off the top of my head I can think of at least 9 series that was involved with the cross over. Some of these arcs have little to do with Tim and others have a lot to do with him, but if I'm listing it it's because it's for you to understand what is happening in the story and to gain a better understanding of Tim Drake and the settings he is in.
Establishment Comics (Comics that place Tim in canon in the past, but he plays no role in that comic)
Batman #436-439 - Year 3
Introduction and Training
Batman #440-442 & New Titans #60-61 - A Lonely Place of Dying (Tim Drake plays a major role and is introduced)
Batman #443-445
Batman #448-449
'tec #615
'tec #618-621 - Rite of Passage (Tim Parents are kidnapped and Batman goes to save them
Important or Character Development comics in Year 1 (Year13) of Tim Drake as Robin
Batman #455-457 (Tim gets the Robin suit)
Robin vol 1 (Tim goes to Paris for Training)
Batman #465 (Tim's first night as Robin)
Batman #466 (A one issue story concerning how Robin views heroes)
Batman #467-469 - Shadow Box (King Snake attacks B&R)
Robin Anual #1 (Tim Drake's first encounter with Anarky as Robin [They met earlier as Money Spider and Unknown boy before Tim was officially Robin])
Robin vol 2 (Tim has to defend Gotham from Joker)
'tec #644-646 - Electric City (A good story with B&R dealing with a vigilante and murderer)
Batman #480 (Jack Drake gets out of the hospital)
Batman #481 (minor scene, Jack Drake buys the house next door... like 1 page, it can be skipped)
'Tec #647-649 (introduction of Spoiler)
Robin vol 3 (Tim and Huntress team up for the first time)
Important or Character Development comics in Year 2 (Year14) of Tim Drake as Robin
Robin Annual #2 : Bloodlines (Introduction of Psyba-Rats)
Batman #488, 'Tec #657, & 658 (Tim Trains Azrael)
Batman - Knight Fall
Batman - Knight Quest
>>> Showcase '93 #11 & 12 (Tim seeks advice from Dick)
>>> 'tec #668 transitions to Robin vol4 #1
>>> Robin #1&2 Robin (Robin escapes the Batcave, meets Shotgun, deals with the Speedboyz, and Arthur Brown escapes Blackgate)
>>> Robin v4 #3-5 (Spoiler & Tim's 2nd meeting. Cluemaster foiled)
>>> Showcase '94 #5, Robin #6, and Showcase '94 #6 (Tim and Huntress team up again)
>>> Robin #7 (Bruce Wayne and Jack Drake return to Gotham)
Batman - Knights End
Robin #10 (Zero Hour caused Tim and Dick Robin Team up)
Robin #0 (Robin and Nightwing talk about the Robins on the past... A recap issue and leads into Prodigal)
Prodigal (Shows Tim and Dick's interaction as Batman and Robin)
Troika (Bruce upgrades Batman and Robin's gear while fighting KGBeast)
Robin #15-16 (Spoiler get's kidnapped)
War of the Dragons (Massive battle between top martial artists)
Robin #19-20 (First meeting with the General)
Robin #21-22 (Tim's first use of Alias Alvin Draper)
Important or Character Development comics in Year 3 (Year15) of Tim Drake as Robin
Batman #526 (Bruce and Tim have an important Talk)
Robin #25-26 (Tim learns a lesson. Spoiler & GA (Connor) appear. Spoiler becomes serious vigilante. Technically starts the issue prior but are the previous 2 issues are an arc that isn't important and everything important from that issue recapped here. Also there is an "end" at the end of #25 but the story continues in #26 save for without GA)
Contagion
'Tec #697-699 (Tim gets Locked in a cell with a bunch of villains, shows his fingerprints are flagged as Alvin Draper)
Legacy
Robin #35 (Robin and Spoiler save people during Final Night)
Robin #40-41 (Tim and Ariana events. Robin and Spoiler team up to take on some Ghost Dragons)
Robin #43-44 (Robin and Spoiler take on the Mighty Baffler!)
Robin #45 (Tim has a bad day ^.^ not essential, but shows a bit of what Tim has to deal with)
Robin #46 (Tim doubts himself. Somewhat of a continuation from #26)
Robin #47-48 (Another General adventure that plays out later on)
Robin #49-52 (Robin goes back to Paris to start his training over and Shiva and King Snake turns up)
Cataclysm
Aftershock
Young Justice: The Secret (The first team up of Robin, Superboy, and Impulse)
Brotherhood of the Fist (sequel to War of the Dragons)
Young Justice #1 (Young Justice officially forms. No other mention save for YJ's dissolution will be mentioned. It's a great read and happens in continuity, but none of what happens in its pages is important. You should still read it though.)
Robin #56-61 (Robin and Spoiler start dating. Spoiler reveals she's pregnant. Tim's friend is murdered.)
Important or Character Development comics in Year 4 (Year16) of Tim Drake as Robin
Road to No Man's Land
No Man's Land
>>> Robin #62-66 (Tim moves to Keystone city, teams up with Flash, and then moves back to Gotham Heights)
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