Since the story has a broad setting but an intensely personal dynamic to dive deeply into, it’s more a relational piece than big action; because of that, you need some high-power talent! If you haven’t read the story, it’s an exploration of heroes through the eyes of a “Robin”, a junior partner to a main hero. It’s a fantastic story, and one that actually uses post-modernism well by asking good questions and then answering them: what defines a hero? What are those qualities? And once we know what makes a hero, what do we decide to do for ourselves with that knowledge?
Since we’re VERY used to Batman films, my first Astro City film would focus on doing what we haven’t seen from caped crusader films: exploring a universe through the eyes of the “sidekick” as he comes of age and learns an important lesson.
So the characters and cast:
Brian Kinney/Altar Boy: Timothy Chalamet
I’m not actually a fan of Timothee Chalamet. BUT… he is the spitting image of Brian Kinney, aka, Altar Boy. I mean, seriously: he could walk in and start playing the role immediately. I haven’t seen much of his work, but if he can actually pull of Paul Atreides, than he has got the stuff for Altar Boy! One of the keys to the character is that he has to look like someone you think you could pick on, right before kicks the holy hell out of you. At the same time, he also needs to portray a wide range of emotions, not all of them positive. So an actor who can convincingly show how to be heroic in public and have a personal crisis partway through the film necessitates an actor who is more than just a pretty face.
I’d much prefer a young actor with a lot of martial arts training who has a bit more muscle on him, but until I can think of one, Timothee will do.
The Confessor: Jason Issacs
The senior hero, the “Batman” for Astro City, if you will. I love the Confessor’s design and appreciate that under the mask, the character isn’t some young, buff 20-something sprout. Without spoiling anything, we find out that the Confessor was initially an immigrant to Astro City and was a clergyman, so it works for him to be older and have an accent.
So to play him, I love Jason Isaacs for the role. He’s mature, distinguished, has a killer voice, and since the costumed character wears a mask, Isaacs doesn’t have to do a ton of martial arts. A stunt double can be subbed in.
Crackerjack: Ryan Reynolds
It’s a short list. Crackerjack is in his prime during this storyline, but coming up in later ones, will be approaching retirement. Reynolds is a great choice because he can do the humor for the role for “Confessions”, and then have the gravitas for a much bigger part of a future storyline of the character being forced into retirement.
Jack-In-The-Box: Denzel Washington/Michael B. Jordan
To me, this is a no-brainer. Denzel is the man: I’ve enjoyed seeing him in films since I was a kid, and he already is a hero in my book! He’s the only actor I’d want to be Jack in “Confessions”, because his very next appearance is a “passing of the torch” story to a successor, played by Michael B. Jordan.
Michael is an incredible talent who has already played super heroes before, and he’s locked down incredibly physical roles that entailed some drama. He’s the perfect candidate to pick up the torch and run with it.
Glue-Gun: Nathan Fillion
It’s a cameo role, what can I say? Fillion has his own series to do, (The Rookie) where he’s the good guy; so a cameo is likely all he could fit.
That said, I think he’d be perfect for the role of Glue Gun, the super-villain who wants to be taken seriously but never is, especially after getting his %^& knocked out by a bus boy in a room full of super heroes.
Mordecai Chalk: Stephen Lang
This one was ridiculously easy. It’s not a huge role, but Lang will crush it anyway.
Gunslinger: Diego Luna
Anyway, that’s off the top of my head. This gets way too long otherwise.
I’d try to stick as closely to Kurt Busiek’s story as much as possible; I think Confession would be an awesome, small introduction into the world of Astro City through the eyes of someone deciding to become a superhero. An unlike a lot of films that focus in on “Batman”, this one focuses on the partner. It’s a fantastic story dealing themes of honor, selflessness, heroism, and of course, fatherhood, since that’s an inciting factor for the whole story.
But most important is the ending message: even after you’ve broken down heroes and seen what’s beneath the mask, great stories, (and true heroes) look to build something back up. Brian Kinney’s journey is all about deconstructing heroes to finally appreciate what it takes to be one, and then choosing to take the hard road himself.