Name a single definitive story for each character

[Batman Begins 2005]

I'll have a bash at the ones I know best...

Batman: Year One
Jim Gordon: Year One
Dick Grayson: Batman Reborn
Damian Wayne: Batman Reborn
The Joker: The Killing Joke
The Riddler: Hush
Two-Face: The Long Halloween

Thoughts on my list?

[HunterDoodle]

Batman: Dark knight Returns
Dick Grayson: Battle for the cowl
Jason Todd: Death in the family
Joker: Killing Joke

[Conway]

Batman: Dark knight Returns
Dick Grayson: Battle for the cowl
Jason Todd: Death in the family
Joker: Killing Joke

See I view Battle for the Cowl not so much as a Dick Grayson story but a story about the relationship between the four Robins. I think they tossed it for the New 52 but it really was the definitive story about those relationships.

Dick asserts himself as the top dog and proves he worthy to train Damian. Jason returns to crime fighting but makes it clear he's not going to do it by Bruce's rules and is forced to accept Dick as the authority of those rules. Tim is almost killed by Jason and fights with Damian, he comes to terms with the fact that it's time for him to go solo and get away from Damian but he's not ready to be the Bat. Damian is a little jerk that approves of Jason's methods but listens to Dick and is there to save Tim's life in the end.

[JBatmanFan05]

See I view Battle for the Cowl not so much as a Dick Grayson story but a story about the relationship between the four Robins. I think they tossed it for the New 52 but it really was the definitive story about those relationships.

Dick asserts himself as the top dog and proves he worthy to train Damian. Jason returns to crime fighting but makes it clear he's not going to do it by Bruce's rules and is forced to accept Dick as the authority of those rules. Tim is almost killed by Jason and fights with Damian, he comes to terms with the fact that it's time for him to go solo and get away from Damian but he's not ready to be the Bat. Damian is a little jerk that approves of Jason's methods but listens to Dick and is there to save Tim's life in the end.

It might be definitive if it were written better (actually, even just well at all), but I found its writing terrible. Too bad Snyder didn't write it. Huge disappointment for me as it should have been this great story to match its importance (now I don't even count it my head canon for Morrison's run). All the characters felt off or bland/generic, especially Jason (Winick wrote Jason infinitely better). Damian is suddenly picking up chicks and incapable of fighting. Black Mask and Jason lack any depth or interesting anything. The story itself is all over the place and ill-focused.

I don't think there is one discrete four Robin story that's definitive (Morrison's amazing run is not singular enough, too many arcs). Maybe this new Eternal can rectify that.

[RubberLotus]

Joker: Fool's Errand (Detective Comics #726)
Two-Face: The Eye of the Beholder (Batman Annual #14)
Penguin: Cracks (Showcase '94 #7)
Poison Ivy: Hothouse (Legends of the Dark Knight #42-43)
Riddler: Questions Multiply the Mystery (Detective Comics Annual #8)
Killer Croc: Requiem for a Killer (Batman #471)
Ra's al-Ghul: Birth of the Demon

[JBatmanFan05]

Joker: Fool's Errand (Detective Comics #726)
Two-Face: The Eye of the Beholder (Batman Annual #14)
Penguin: Cracks (Showcase '94 #7)
Poison Ivy: Hothouse (Legends of the Dark Knight #42-43)
Riddler: Questions Multiply the Mystery (Detective Comics Annual #8)
Killer Croc: Requiem for a Killer (Batman #471)
Ra's al-Ghul: Birth of the Demon

Can't much argue with those. I like that you went with less obvious and popular ones.

Birth of the Demon is such a great origin for Ra's (and Norm's art doesn't hurt either!). I didn't read it right way, but when I did, I thought it was such a great tragic and sympathetic origin for such a tyrant as Ra's. The sheer injustice against him & his wife, after all they did. You feel as sated as Ra's when you see him getting his revenge.

[TheBatman]

Bruce Wayne-Batman: R.I.P
Dick Grayson: Batman Reborn
Jim Gordon-Batman: Year One
The Joker-The Laughing Fish
Two-Face-The Long Halloween
Ra's Al Ghul-Tales of the Demon
Harley Quinn-Mad Love

[doolittle]

Jason Todd: Difficult to pick. There`s For The Man Who Has Everything/Under The Red Hood/The Cult. But UTRH is the definite modern Jason story.

Damn, do I love Jason in The Cult. Read it for the first time a few weeks ago.

[batnbreakfast]

Bruce Wayne- Year One (Miller)
Barbara Gordon- Batgirl Year One (Beatty?)
Black Mask- Catwoman (Brubaker)
Two-Face- Gotham Central/Half a life (Rucka)
Ra's Al Ghul- Death and the maidens (Rucka) don't care for Bond villain Ra's

[Zainu]

Hmmn. Honestly, all of Cassandra's early Kelley Rucket run issues all served well as stand-alone stories, but honestly, if I had to pick one..then...the one where Cass had to face down Shiva. I loved that one, and I think that the character exploration done there really showed Cass's true mettle/colors. Get her first run(or at least, issue #1-10).

Be warned though, Cass is too lovable, and once you fall in love, there is no going back(at least, that was the case for me).

[H4l3quin]

Batman-Year One
Joker-The Killing Joke / Batman 663 / Going Sane (I can't decide)
Scarecrow-Cycle of Violence
Bane-Knightfall
Riddler-Zero Year
Two Face-Long Halloween

[heyevaxx]

I'll toss out two more Cass Cain definitive story options:

Batgirl v1-33 2002-12 "Father's Day" Puckett/Scott
This is the one where she goes in disguise to Blackgate to try to get some info from her father. But memories of Cain's murder and framing of Bruce and of Cain's training/abusing her overwhelm Cass and she explodes. "Who do you think you are?!" after smashing through the bullet proof (but not Cass proof!) glass. The art, dialog, pacing, everything is perfect. And we even get a bonus scene at the start with Cass hitting a meta "hard enough to crush a human skull." And wow! was it ever a hard hit! The final scene with Bruce giving her a gift is one of their nicest moments.

Batgirl v1-50 2004-05 "Tough Love" aka "Batgirl vs. Batman" Horrocks/Leonardi
This was the iconic showdown between a willful teenage fighting savant and a micro-managing hyper-controlling vigilante overlord. Who won? The readers! This was the culmination of friction between Cass and Bruce the culminated in a fight under Bruce's direction. He wanted to find her true allegiance and he knew that she can best communicate through motion and fighting. In the end, she's claims to follow no person - not her parents, Babs, or Bruce - but the Bat symbol and what it represents. The final bit was gold with Bruce and Babs talking. I love Babs saying "You're crazy" after he explains this was therapy and his reply "So they say, but it works" with a smile. So good!

[JBatmanFan05]

Batman #663 "The Clown at Midnight"....I reread it recently and it's even more brilliant and subtle than I even remembered, maybe it's more definitive than I previously thought. It's almost or perhaps underrated. What the story doesn't get credit for enough is how Grant humanizes Joker in it. My new favorite line in it is: "Maybe he is special, and not just a gruesomely scarred, mentally-ill man addicted to an endless cycle of self-annihilating violence. Stranger things have happened."

[Unfinishedsentenc]

Zero Year is a Bruce Wayne story so for Riddler I'd say either "Riddler's Reform" from BTAS or the 1995 Detective Comics Annual #8 (my personal favorite). For some of the others:

Mad Hatter - Mad as a Hatter (BTAS)
Joker - Either Killing Joker or Return of the Joker
Killer Croc - Joker's Asylum: Killer Croc
Zsasz - Hardcore Nights (Streets of Gotham run)
Clayface - Mud Pack
Harley - Mad Love (BTAS)
Ivy - House and Garden (BTAS)

[Unfinishedsentenc]

Batman #663 "The Clown at Midnight"....I reread it recently and it's even more brilliant and subtle than I even remembered, maybe it's more definitive than I previously thought. It's almost or perhaps underrated. What the story doesn't get credit for enough is how Grant humanizes Joker in it. My new favorite line in it is: "Maybe he is special, and not just a gruesomely scarred, mentally-ill man addicted to an endless cycle of self-annihilating violence. Stranger things have happened."

Yeah, that's a great one. Harley was spot-on too (and actually used as a tool to help humanize Joker in this case). One of my favorites.