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)

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