In a September essay at The Comics Cube, Duy wrote, “A lot of comics fans - myself included - would name Dick Grayson as one of their all-time favorite characters. . . . But then if you ask people to name an all-time great Nightwing story, you’d be hard-pressed to get straight answers.”
Duy suggests that Nightwing is just too well adjusted and anchored to create opportunities for great solo tales:
Dick Grayson was the coolest guy in the DC Universe. He was the best big brother you never had. And he was so with it, so together, that there was nothing wrong with him at all. And that was the problem. . . .By which Duy means the pre-1960s, no-faults, catch-the-villain-in-one-issue hero. That would indeed mean little angst, suffering, or frustration. (Which brings up the question: are those elements necessary for a “great” modern superhero story?)
The uncertainty that came with being Robin and the utter detachment and awesomeness (in the purest sense of the word) that came with being Batman wasn’t his. He could look Superman straight in the eye and tell him the real score. And because of the way the DC Universe worked, he couldn’t be put through the wringer like Daredevil has continually been. If you hurt Dick, Batman will come. If you take away his home, his money can buy him a new one. You can’t kill his supporting cast - they haven’t been around long enough for you to form an attachment to them. You can’t introduce things from his deep and dark past, because we’ve already seen his past. He was Robin. We’ve read and seen his adventures. So you can’t mine that.
What’s left when you’ve got an ultraconfident guy with no hang-ups with extraordinary abilities fighting crime? You’ve got, and I hate to say this, a generic superhero.
Duy’s suggestion for making the Nightwing magazine work starts with on “his greatest personality strength, which is his ability to lead and command respect from the entire DC Universe.”
But that of course leads to another, perhaps more powerful answer to why naming great Nightwing solo adventures is tough: because he appears in great stories with other characters. Created as a sidekick, Dick Grayson was defined from the start through his link to another hero; most other comics crime-fighters started as the only hero in their worlds. As Nightwing, Dick remains one of the most important characters in the Batman ensemble. And the character came into his own in a team magazine, The New Teen Titans.
Thus, for respected and beloved stories featuring Nightwing, we can start with The Judas Contract, the story by Marv Wolfman and George Pérez in which Dick takes that crime-fighting identity. That’s #13 in Brian Cronin’s November 2009 fan poll about favorite comics storylines, and on io9’s list of 75 DC Comics volumes every rich fan should own.