Well, if you’re specifically looking for good stories featuring Grayson as Batman, I’ll recommend two:
The Black Mirror, which was written by Scott Snyder, and drawn by Jock and Francesco Francavilla (which is a criminally fantastic creative team). It ran in the last nine issues of the first volume of Detective Comics.
Also (sort of) by Snyder, I’d recommend Gates of Gotham, which is a miniseries. It was plotted by Snyder, and scripted by Kyle Higgins. It was drawn by Trevor McCarthy and Dustin Nguyen.
As for Dick Grayson stories in general, I’d check out Grayson, the DCYou series written by Tom King and Tim Seeley, and drawn by various artists, but mostly Mikel Janin, and the Rebirth volume of Nightwing, up until issue 50, where it goes totally off the rails.
I’m going to agree with Batwing52’s recommendations. I just finished Grayson (it’s here on DC Universe) and it’s fantastic. Nightwing Rebirth takes place right after the Grayson series ends, so you may want to read Grayson first. However, it is not vital to the understanding of Nightwing Rebirth.
Chuck Dixon’s run on Nightwing’s first solo series in the 90s/00s explored Dick choosing his own town and reconnecting with the Batfamily. There are some good Nightwing and Robin bonding moments in the series (with Tim and Jason). The Great Leap arc at the end of that series was interesting and leads into stories that push Dick into becoming the Bat.
If you like Dick and Damian’s relationship, Nightwing 2016- #42 is a story told by Damian about his awesome brother coming to his rescue.
I’m thirding Batman: Black Mirror. Hands down, one of my favorite Batman stories ever, and certainly one of my favorite Scott Snyder stories. It’s pretty dark though, so just know that. It has a couple of graphic images.
I’ll also second Grayson. It was one of the first series’s I read on this app (a long while ago now) and I enjoyed it a bunch. Not the biggest Tom King fan in general, but between Grayson and Mr. Miracle, he’s got some decent work. The fact that he’s an ex-CIA officers gives him a unique perspective for Grayson—which is more of a spy thriller story than a traditional Nightwing superhero story.
Im a big Scott Snyder fan so I’ll probably read Black Mirror next. I’ve heard good things about the Grayson series as well so I was probably going to check it out while on my Grayson kick. Thanks for the recs!
I can’t speak on Dick as Batman cuz I’ve never gotten around to any of that. But definitely read Grayson! It’s honestly my favorite series of the character. Chuck Dixon’s run is close after that. And when it comes to Rebirth, Seeley kinda lost the spark from Grayson. It really started getting good when they changed creative teams. The Untouchable was great! The Bleeding Edge was interesting. I really liked the take on Dick’s relationship with technology, but sadly that story was never finished because of Batman #50 and the terrible amnesiac Ric fiasco.
For more of Dick and Damian’s relationship you might wanna read Nightwing Must Die, and issues #42 and #43 all from Rebirth. Issue #43 also includes Arsenal if you’re interested in him. His interactions with Damian are hilarious and Nightwing kinda plays the parent.
And the first 9 issues of Kyle Higgins run on Nightwing (Traps And Trapezes and Night Of Owls) are actually way better than most people will give them credit for. But from what I understand if you like Dick’s run as Batman you’d like his run.
I’ll lend another voice of support for Grayson, as it was the best New 52 book to star Mr. Grayson.
As for Dick in Rebirth, I found Nightwing to be all over the map, very hit and miss. Rather, give Titans a whirl instead.
Dick is still front and center as the leader of the Titans, but the book also provides insights into the friendships he has with everyone on the team while being far more entertaining than Nightwing has ever been.