#ugh....the hesitation to put Titans Vol. 1 on here but knowing it portrays his relationships with the rest of the Fab Five the best...

[fantastic-nonsense]

i don't know if you've already made a post about this but what comic(s) do you think have the best characterisation of cassandra cain and dick grayson?

My instinctive response to this ask was to just answer "Prodigal and Batgirl (2000)" and be on my way. Instead, I took a little bit more time to think about what my answer should be and what information might be useful to people looking for comics featuring a well-characterized Dick and Cass. So, with that said:

Dick:

Robin: Year One (2000)

New Teen Titans/Tales of the Teen Titans (1980 & 1984)

Batman: Year Three (1989)

Batman: Prodigal (1997)

Titans Vol. 1 (1999)

Nightwing/Birds of Prey: The Hunt for Oracle (2000)

Gotham Knights (2000) #1-12

Peter Tomasi's run on Nightwing (1996)

Batman: The Black Mirror (2010)

Batman: Gates of Gotham (2011)

Listen. All of these comics have their flaws. Many of them feature dated and occasionally poor treatment of various characters/social issues. I'm still holding a grudge against Devin Grayson for her Nightwing run and will until the end of time, and thus the inclusion of Titans Vol. 1 and her first Gotham Knights arcs might seem a bit odd. But I also think this is a pretty solid list of comics that portray Dick in ways that feel consistent and faithful to his core characterization; they're also some of the comics that feature Dick at his best.

Cass:

Batgirl (2000): specifically the Puckett/Scott run (#1-37) and the Gabrych run (#38 & #58-73)

Bruce Wayne: Murderer?/Fugitive (2003)

Gates of Gotham (2011)

Tynion's run on Detective Comics (2016)

Batman and the Outsiders (2019)

Batgirl Vol. 1 was and continues to be the golden standard of how to portray Cass. She's never reached those heights again. Other comics featuring Cass wish they were Batgirl Vol. 1, but it was a true "lightning in a bottle" run that has yet to be replicated. That being said: Murderer/Fugitive (which takes place during Cass's Batgirl run) is great, and Gates of Gotham features the only solid pre-reboot Cass characterization post-Evil Cass arc.

Post-Flashpoint!Cass is a bit of a different animal, but within the context and limitations placed on her appearances until Dan Didio's departure from DC in 2020, she's best characterized and treated in Detective Comics Rebirth and Batman and the Outsiders.

Honorable mentions: these comics either weren't quite on the same level of "good characterization" to make the list or just didn't highlight the character as much as they could have, but I still really like what the creative team did with them in the space they were given:

Dick: Nightwing (1996) #6 (for being a fun depiction of Dick and Tim's early-days relationship), Teen Titans (2003) #6 (great characterization of Dick. So-so characterization of...several other characters), The Resurrection of Ra's Al Ghul (I love Dick's characterization here, and it's one of my favorite Bat books, but he's just not in it all that much), and Batman & Robin (2009), which...I'll get into my complicated feelings about Morrison's B&R run some other time, but generally: I like Dick's characterization in this comic a lot in isolation. It becomes much more difficult to square, however, when you take everything else going on during the Reborn era into account.

Cass: Mariko Tamaki's Shadows of the Bat: The Tower (2021) event and "Sounds" short from the DC Asian Superhero Celebration (2021) anthology. They're nice and have some great Cass moments, but they're either too short (Sounds) or too focused on other characters/the overall plot (The Tower) to truly do her justice.