Chuck sure did love writing about those Batboys. Here’s a 3-volume map of his lengthy stint on Nightwing.
Nightwing Annual 1
Batman Annual 23
Nightwing Secret Files & Origins
Birds of Prey 20
Birds of Prey 21
Action Comics 771
Nightwing 80-Page Giant
Nightwing: Our Worlds at War
Nightwing: The Target
Batman: The 10-Cent Adventure
Batman 600 (minus the backups)
Batman Annual 23 is part of the JLApe annual crossover, but it’s basically a extended (and pretty fun!) Nightwing one-shot. This is where Blockbuster meets and takes in Grimm the gorilla, which plays a key role in the “Hunt for Oracle” crossover soon to follow.
Nightwing 23 is part of the “Brotherhood of the Fist” crossover & Nightwing 53 is part of the “Officer Down” crossover.
Action Comics 771 is where Nightwing (with Supes’ help) takes down Torque’s Intergang suppliers. Superman/Nightwing team-ups are always fun, and Chuck writes them both perfectly here. This is actually one of the best Nightwing issues he wrote, IMO.
I left in the beginning and conclusion of the Bruce Wayne: Murderer/Fugitive storyline so the Nightwing comics during that time made sense. Batman 600 portrays a key relationship change between Dick and Bruce, and with Scott McDaniel back on art duties, it fits right in. I think it definitely needs to be included, even if you leave out The 10-Cent Adventure & Batman 605.
Nightwing Annual 1 chronologically takes place before the entire series, but putting it first would be weird, so I just stuck with publication order. It’s also by Devin Grayson, not Dixon, and is completely standalone, so it could be removed if you really wanted, but it’s a good story and Greg Land seems to actually be drawing people instead of tracing them at this point in his career.