Dick Grayson has been around since 1940, so you could do a lot of reading. If you're just getting into the character, trade paperbacks are a good way to go because you get a complete storyline. If your funds are limited, check your local library!
The Basics
Batman: Dark Victory - contains a recent origin story
Batman Chronicles: The Gauntlet - Dick proves he is street ready
Robin: Year One - modern version of Dick's first year as Robin
Teen Titans: Year One - modern version of how the Teen Titans began
New Teen Titans: The Judas Contract - the original debut of Nightwing back in 1984
A Lonely Place of Dying - the origin of Tim Drake but Dick really shines in this story arc
Nightwing: Year One - more recent (2000s) version of how Dick became Nightwing
Infinite Crisis - DCU-wide story that really brings home Dick's importance to Batman and the DCU
Batman: Battle for the Cowl - events that lead up to Dick becoming Batman
Batman: The Black Mirror - the darkest (and probably best) story of Dick as Batman
*Dick Grayson really comes into his own as a leader and an independent hero in New Teen Titans. If you have the time and are interested in deeper background to the character, read some of this series.
Nightwing Solo Series (1996-2009)
Nightwing: A Knight in Bludhaven (solo series #1-8)
Nightwing: Rough Justice (#9-18)
Nightwing: Love and Bullets (#1/2, 19, 21-22, 24-29)
Batman: Cataclysm (includes Nightwing #19-20)
Nightwing: A Darker Shade of Justice (#30-39, Secret Files #1)
Nightwing: The Hunt for Oracle (#41-46; Birds of Prey #20-21)
Nightwing: Big Guns (#47-50, Secret Files #1, Eighty-page Giant)
Nightwing: On the Razor’s Edge (#52, 54-60)
Batman: Officer Down (includes issue #53)
Batman: Bruce Wayne Murderer? (includes issues #65-66)
Batman: Bruce Wayne Fugitive (includes issues #68-69)
Batman: War Games (includes issues #96-98)
Nightwing: Year One (#101-106)
Nightwing: Mobbed Up (#107-111)
Nightwing: Renegade (#112-117)
Nightwing: Brothers in Blood (#118-124)
Nightwing: Love and War (#125-132)
Nightwing: The Lost Year (#133-137, Annual #2)
Batman: The Resurrection of Ra’s al Ghul (includes issues #138-139)
Nightwing: Free Fall (#140-146)
Nightwing: The Great Leap (#147-153)
Batman: R.I.P (Batman #676-683)
As Batman
Batman: Prodigal - takes place when Bruce's back was broken by Bane
Batman: Long Shadows (Batman #687-691)
Batman: Life After Death (Batman #692-699)
Batman: Time and the Batman (Batman #700-703)
Batman: Eye of the Beholder (Batman #704-707, Batman #710-712)
Batman: Gotham Shall Be Judged (Batman #708-709, Red Robin #22, Gotham City Sirens #22,
Azrael #14-18)
Batman and Robin: Batman Reborn (#1-6)
Batman & Robin: Batman vs. Robin (#7-12)
Batman & Robin: Batman and Robin Must Die! (#13-16; Batman: The Return)
Batman & Robin: Dark Knight vs. White Knight (#17-25)
Batman: Gates of Gotham
Justice League of America: Team History (#38-43; Dick only in 41-43)
Justice League of America: Dark Things (#44-48)
Justice League of America: Omega (#49-53)
New Teen Titans and Outsiders
The New Teen Titans Omnibus (collecting all of the NTT stories)
The New Teen Titans: Terra Incognito
New Teen Titans: Who is Donna Troy?
New Teen Titans: Terror of Trigon
JLA/ Titans
JLA: The Obsidian Age - Dick leads the JLA as Nightwing
Outsiders: Looking for Trouble (#1-7)
Outsiders: Sum of All Evil (#8-15)
Outsiders: Wanted (#16-23)
Outsiders: The Insiders
Outsiders: The Good Fight (#34-41)
Outsiders: Pay as You Go (#42-46)
Outsiders/Checkmate: Checkout (#47-49)
Teen Titans/ Outsiders: The Death and Return of Donna Troy
Titans: Old Friends (#1-6)
Titans: Lockdown (#7-11)
In case you are interested in the old stuff:
The Batman Chronicles (reprinting all comics in order starting in 1939; 11 vols. so far)
Batman Archives (reprints Batman stories from Detective Comics)
Batman: The Dark Knight Archives (reprints of Batman from Batman)
Batman: World’s Finest Archives (reprints World’s Finest Batman stories)
Batman: The Dynamic Duo Archives (reprints of Batman and Detective Comics issue starting in 1963; the other Archives start in 1939)
The Robin Archives (reprints Robin’s solo stories from Star-Spangled Comics)
The Silver Age Teen Titans Archives (reprints original Teen Titans from the 1960s)
Showcase Presents Batman (reprints of Batman and Detective starting in 1964; eventually moves into the 1970s when Batman and Robin had solo adventures)
Showcase Presents Robin the Boy Wonder (reprints Robin solo stories from late ‘60s and early ‘70s)
Showcase Presents Teen Titans (reprints the original Teen Titans series of the 1960s and 1970s; two volumes so far, which is about 2/3 of the run)
The New 52
Nightwing: Traps and Trapezes - He learns dark secrets about his past
Nightwing: Night of the Owls - He continues to learn about his past and connection with the court of owls
Nightwing: Death of the Family - The Jokers comes after each Batfamilly members. To get to Dick, he distroys Haley's Circus that Dick had rebuilt.
Nightwing: Second City - Dick moves to Chicago to find more about his parent's death
Nightwing: Setting Son - Even after moving away from Gotham, he is still haunted by it.
Forever Evil - Dick Grayson's secret identity is revielded to the world
Grayson: Agents of Spyral
Grayson: We All Die At Dawn
Grayson: Nemesis
Grayson: A Ghost in the Tomb
Rebirth
Nightwing (2016) - Dick Grayson returns to his Nightwing identity and becomes the protector of Bludhaven for the first time in the Rebirth Universe.
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