Happy Monday, Geekly Gang! Kyra Kyle here with another Geekly Casting. Today’s subject, the comic strip Dick Tracy, is a special case. First, Hollywood already made a Dick Tracy movie in 1990. Second, Warren Beatty retains the rights, so he or someone from his estate on his behalf would have to sell the rights. Third, 1990’s Dick Tracy film was the third story in a proposed trilogy. I mentioned the True Hearts and Tommy Guns Trilogy in a previous Whatcha Reading. I won’t rehash what I said in that post, but we are looking at potential prequel territory. Shooting Dick Tracy as the trilogy it should have always been made into could involve making the first two films, letting the original stand as the final film in the trilogy. Or Hollywood could reshoot and reimagine the finale. Either way works.

It could only be a matter of time (perhaps within the decade) before Dick Tracy gets a reboot, so we’ll be casting a potential movie. Another issue I found while compiling this list is Dick Tracy’s massive cast. 1990 Dick Tracy features dozens of villains. While our Dick Tracy, beginning with Dick Tracy: Big City Blues, trims a lot of that fat, we’re still left with nineteen characters. Yikes! I may go through our justifications quickly. Let’s kick things off with Geekly’s Casting Call for Dick Tracy.

Dick Tracy: Henry Cavill

Originally, I had cast Jon Hamm as Dick Tracy, but he was a little old for who I had cast as Tracy’s love interest, Tess Trueheart. And then I saw this picture (above) of Henry Cavill. Yep! Cavill may make a more convincing Dick Tracy than he ever did Superman. Give him a clean shave, a haircut, and the proper attire, and Cavill is Dick Tracy.

Tess Trueheart: Deborah Ann Woll

Deborah Ann Woll has done it all as an actor. She brings life to comedic, dramatic, and action roles, and she’ll need to tap into all of that with Tess Trueheart. At times, Tess can be Dick Tracy’s empathetic better half with a razor wit. And at others, she’s unafraid to mix it up with some of Tracy’s rogues.

While Tess is depicted as blond in the comics, Dick Tracy (1990) gave Tess red hair to differentiate her from Breathless Mahoney. This was a good choice, and I wouldn’t mind another redheaded Tess Trueheart.

Emil (Pops) Trueheart: David Schwimmer

To the best of my knowledge, David Schwimmer has never portrayed an older father-figure, and I’d like to see him in a role like that. Pops Trueheart doesn’t show up for too long in the Dick Tracy Trilogy–he famously passes away in the comic strip–but Schwimmer could give a memorable performance as Pops Trueheart before the fateful night.

Lilly (Momma) Trueheart: Connie Britton

Since I went with an actor I’ve never seen as a warm and doting father-figure, I had to cast someone like Connie Britton as Lilly (Momma) Trueheart. Despite Dick Tracy‘s setting of Chicago (gangsters and all that), I always read Momma Trueheart with a Southern drawl. I don’t know why. When I put both of these aspects together, I came up with Connie Britton. Britton pulled off a convincing drawl in Friday Night Lights. Hi, y’all.

Chief Brandon: Idris Elba

Honestly, I saw a picture of the classic Chief Brandon and immediately thought of Idris Elba–sorry, Sir Idris Elba (congrats!). I struggled to cast a diverse group of actors in Dick Tracy and had to go with instincts like this as much as I could. We’re talking Chicago in the Twenties and early Thirties, so diversity can prove difficult. Elba is one heck of an actor, and Dick Tracy will need an accomplished actor to portray Chief Brandon.

Pat Patton: Tom Hiddleston

Does Tom Hiddleston look the part of Pat Patton? Maybe. The two may be close enough in appearance, but Pat occupies an odd space in Dick Tracy lore. He has as much, if not more, experience than Dick Tracy, which is why he eventually takes over as Chief after Brandon leaves the role. So, Patton’s actor should slot somewhere close to Tracy’s age, younger than Chief Brandon, and definitely older than the next character on this list, Sam Catchem. In some media, Patton is portrayed with a slight Irish accent. Hiddleston isn’t Irish, but I’d like to hear him try a slight Irish accent.

Sam Catchem: Jeremy Allen White

Sam Catchem is new to the force. He’s as likely as Tracy to get involved in action sequences, and Jeremy Allen White is just the man for those action sequences. He pulled off some crazy moves as Kerry von Erich in The Iron Claw. White didn’t look too similar to Kerry, but you know who he looks more like? Sam Catchem. And White is one hell of an actor.

Steve the Tramp: Josh Brolin

Because of his look as Marv in Sin City, I first thought of Mickey Rourke to play Steve the Tramp. Rourke could still play the role today, but I don’t know about five to ten years from now. Brolin could also give a stellar portrayal of the small-time crook who uses children to commit crimes. Through most of the Dick Tracy Trilogy, Steve the Tramp is reprehensible. Good thing whoever portrays the character will do so under a mountain of prosthetics.

The Kid (Junior): Unknown

The Kid, the eventual Dick Tracy Junior, is impossible to cast given the parameters I set for myself. The rights to Dick Tracy will, at best, become available in the next five to ten years. Any young actor I could cast as The Kid, would age out of the role by the time Dick Tracy would become a reality. In fact, we’d have to cast an extremely young actor (like under eight years old when the movies begin, so I may have to cast someone who hasn’t even been conceived). Eek!

Patricia “Breathless” Mahoney: Ever Anderson

Ever Anderson (Evelyn Nesbit from The Artist) may seem like she’s on the young side to portray Breathless Mahoney, and you might be right if Dick Tracy began filming tomorrow. But the Patricia Mahoney we’ll see in Dick Tracy: Big City Blues is a Mahoney who’s unsure of herself. She reads very young. Patricia grows into Breathless Mahoney, and Ever Anderson could easily pull off this metamorphosis.

Mahoney also begins the Dick Tracy Trilogy as a brunette. She doesn’t transition into a blonde until after she’s under Texie Garcia’s control.

Ribs Mocca: Adam Driver

Ribs Mocca barely appears in the original Dick Tracy movie. You may think we don’t need an actor of any acclaim for Mocca, but Mocca’s a far bigger deal in the True Hearts and Tommy Guns’ first two storylines. A war rages among Mocca, Lips Manlis, and Pruneface, with Texie Garcia flying under the radar with her own hustles. Adam Driver as Mocca makes sense because Mocca is the most junior of the mob bosses. He obtains incriminating evidence on Manlis and uses it to weasel his way into a higher position. Driver would make an excellent Ribs.

Lips Manlis: Bill Hader

Like so many other Dick Tracy villains in the 1990 movie, Lips Manlis didn’t get nearly enough screen time. Manlis is one of the biggest crime bosses. Heck. Big Boy Caprice begins the Trilogy working for Manlis. That scene in Dick Tracy, where Big Boy puts Manlis in the bath, was cathartic. And Manlis is a devilish bastard you love to hate. With the context of the previous two stories, fans will cheer Big Boy giving Manlis the bath.

With that said, Bill Hader may be an odd choice for Lips Manlis, but Hader has proven he can play this character type. Hader’s star turn as the title character in the dark comedy Barry proves he can play an unhinged character with a ton of depth. And Manlis requires depth and can get unhinged.

Pruneface: Michael Shannon

Michael Shannon as Pruneface may be typecasting, but I don’t care. Pruneface is another one of the major crime bosses. He specializes in sabotage and explosives. Not necessarily in that order. Whoever portrays Pruneface needs to have presence, and Shannon has proven he has that in spades.

Texie Garcia: Shorhreh Aghdashloo

I love Shorhreh Aghdashloo’s iconic husky voice. Texie Garcia is yet another crime boss (albeit one who hides in the shadows) and needs to have an actor with plenty of gravitas. Aghdashloo’s voice oozes cool. She looks the part. She may be on the older side to portray Garcia, but Garcia barely shows up in the Dick Tracy movie (the third story of the Trilogy). Instead, she dominates Mahoney’s origin in the first two stories.

Numbers: Stanley Tucci

“Numbers” Nelson is one of those rare made-for-the-1990 Dick Tracy movie characters. The only comic book you’ll find Numbers in is the True Hearts and Tommy Guns Trilogy. While Numbers eventually works for Big Boy Caprice, who’s more of a minor character in the beginning, he starts as Texie Garcia’s accountant. Brilliant character actor Stanley Tucci could give a great performance as Numbers without breaking a sweat.

Jack “Big” Frost: Sean Bean

At first, I had cast Sean Bean as B-B Eyes and DJ Qualls as Jack “Big” Frost, but I couldn’t pass up a funny and swapped the two actors. Minor Spoiler: Jack “Big” Frost dies at the end of the first movie, Big City Blues. We have to keep Sean Bean’s streak of dying in movies alive.

B-B Eyes: DJ Qualls

Again, I had DJ Qualls as Jack “Big” Frost and swapped him for B-B Eyes. I didn’t care for this side of the swap, but it grew on me. First, Qualls doesn’t usually get too many prominent roles, and B-B Eyes is one of the second story’s focal points. Second, Dick Tracy puts on a B-B Eyes mask and goes undercover as the mobster, and watching Henry Cavill putting on a DJ Qualls mask would be amazing. Finally, I can see Qualls as B-B Eyes. He may be a better choice than my original pick, Sean Bean.

Big Boy Caprice: Paul Giamatti

While Paul Giamatti would never get confused with Al Pacino, he looks more like the comic strip version of Big Boy. Pacino gave a good performance in the original Dick Tracy film. The movie didn’t work in a lot of ways, but none of those ways was because Pacino gave a flat performance. But Big Boy begins the Trilogy as a mouse. Caprice becomes Big Boy over the course of the first two stories. Giamatti would have no problem pulling off this kind of character arc.

Flattop: Keanu Reeves

While researching this post, I saw someone else fan-cast Keanu Reeves as Flattop “Jones.” I can see that. Flattop is Dick Tracy’s most recognizable and beloved foe. He was even the first comic strip character to receive a funeral. People mourned the loss of Flattop like they would the loss of a loved one. Why not cast a beloved actor as Flattop? It also doesn’t hurt that Flattop could’ve been John Wick in another timeline and with a different moral compass.

Mumbles: Jeremy Renner

Mumbles is another character where I saw the picture and immediately thought of an actor: Jeremy Renner. I may have seen a caricature of Renner that looked exactly like Mumbles. And Mumbles is yet another popular Dick Tracy villain. Even though his name is Mumbles, Mumbles doesn’t mumble. He speaks too fast and slurs his words. I could see Renner having fun with the character’s speech patterns, but when push came to shove, and a dramatic moment was warranted, Renner could dig deep for Mumbles’s inner calm.

88 Keyes: Leonardo DiCaprio

88 Keyes (or Keys), named after the 88 keys on a piano, is nothing short of a lady’s man. In the Dick Tracy Trilogy, 88 Keyes may be a little older than he was originally in the comic strip, but he remains a man who gets by on his looks. DiCaprio may have some experience with that. It also doesn’t hurt that 88 has underhanded plans for days. He lets everyone think he only cares about the ladies, but he has real criminal ambitions. DiCaprio knows how to obfuscate his character’s true intentions. He’d make a dapper 88 Keyes.

Those are my picks to portray Dick Tracy characters in a hypothetical Dick Tracy Trilogy. Who would you cast? Let us know in the comments. Thank you for reading, and wherever you are, I hope you’re having a great day.