After his latest comic project, writer Marc Guggenheim has "Riddle Me This?" on the brain.

The executive producer of The CW's superhero drama "Arrow" has made a home for himself at DC Entertainment's digital comics division, where tie-ins to his TV show and a recent "Adventures of Superman" serial have allowed him to stretch his comics writing muscles. Starting tomorrow, Guggenheim's latest digital-first work debuts -- a new "Batman: Legends of the Dark Knight" three-part tale with artist Federico Dallocchio centering on the Riddler. And for this project, the writer is getting more interactive with digital readers and readers of this interview.

CBR News spoke with Guggenheim about the story, and the writer explained what drew him towards a new kind of take on Edward Nygma and the special features digital readers can unlock if they're clever enough. He also offers fans a chance to win something from his own personal collection if they can answer a riddle of his devising via Twitter.

CBR News: Marc, "Legends of the Dark Knight" is your latest comics project for DC Entertainment. With jobs like this and your recent "Adventures of Superman" story, do you find yourself saying things like, "I have one killer Batman story to get out," or is it more of a challenge to yourself to craft a one-off story with the character in this digital format?

Marc Guggenheim: I think it's more the latter. I didn't have a Batman story burning a hole in my pocket. I've always wanted to write more Batman -- I did a "Batman Confidential" arc a couple of years ago, and that's obviously a favorite character of mine, as I think he's a favorite of most people's. But all the Batman ideas I had in my notebook didn't really work in the 30-page space of the "Legends of the Dark Knight" series. So for this project, I started from ground zero and asked myself if there was a story I could tell which would work in this medium. I started by thinking in terms of villains, because when you're doing something that's out of continuity and thus is more of an evergreen story, you want to make a statement about Batman as opposed to do something that's going to affect his life.

When I was thinking about my statement about Batman, my mind immediately went to his antagonists. Right away, I ruled out people like the Joker, because I didn't think at this time I had anything new to say there. I thought a lot about who's interesting, and my thoughts started to trend towards the Riddler, a really interesting character because he's sort of Joker-esque. He's got this gimmick where he's always sowing the seeds of his own destruction. And the more I thought of that, the more I saw this really interesting psychological dynamic to play with. Batman functions so well in the psychological space since he's such a psychologically evocative character, so the idea of a villain that is basically self-destructive is really intriguing, and I don't think many people have explored that with the Riddler. I'm always trying to tread new ground, and the more I thought of this, the more I felt it would be an interesting arena for that. I thought it gave me a chance to reinvent the Riddler a bit. Because this is an evergreen, I have some latitude on that. I don't want to spoil the end of the story, but you'll see by then that this is a Riddler pretty different from any we've seen in the comics before.

RELATED: Guggenheim's "Adventures of Superman" Questions Everything You Know About the Man of Steel

The Riddler is one of those villains who's more clever than most of us. Was it a challenge to make this case compelling as you thought up riddles and clues for him to leave Batman?

I approached him from the standpoint that he's ten times smarter than I am, and ten times smarter than Batman. That makes him less of a punching bag and more of an interesting villain. I guess you could say that I tried to take a [Christopher] Nolan-esque approach to the character. I wanted him to be formidable and be Batman's equal, if not superior. So yeah, that required me to come up with a lot of interesting clues, and in keeping with the spirit of riddles and clues, I embedded little codes and odd tricks into the comic itself. So part of the fun of this experience is that it's interactive. If you figure out the clues, you'll be able to download my draft of the script.

That's a new wrinkle for your digital work. Since this is your third assignment in this space, after the "Arrow" digital comics and the Superman story, do you feel a bit more confident in being able to play with the format in those ways?

I've really enjoyed working with [editor] Alex Antone. What's really great about working with him is that he encourages me to take crazy risks and try different things. He's always game for the nutty stuff I have to pitch, and when it came to this idea, he was all in. I hope it works. It's tricky to craft something that's challenging enough that not a million people can solve it, but you don't want to do something so obscure and so obtuse that no one could crack it. And I'm not exactly a game designer, so this is a bit of a new venture. Actually, do you want to have some fun with this?

Always!

Okay, the title of the storyline is "Herded Limits." The first person who Tweets to me what the significance of the title is, I'll send something cool to them. It's a weird title, but there's definitely a meaning to it. I'll leave it to the readers to see who can figure it out first.

Your artist on this series is Federico Dallocchio who is a new name to a lot of readers. It seems the digital stories leave some more leeway on the artist's drawing board. What has he done with this story?

What Federico's done is that he's really embraced the evergreen nature of this. His Riddler is both evocative of Riddlers past -- because the character has had many looks over the decade -- but also feels really unique and new. He's also a little younger, which is cool. Usually he's drawn as a bit of an older man, but he's given our Riddler a youthful exuberance which plays into the character itself and our take, which as I said is different than has been done before.

And his Batman is wonderful. It's funny; we didn't even talk about what Batman's costume should be, but he instinctively drew my favorite version, which is the one with the more oval-ish Bat Symbol on it. It's got an old school utility belt. There's just a vibrancy and dynamism to Federico's style that I think really works for this book. Even with 30 pages to play with, the panel-to-page ratio is kind of killer, and Federico did a wonderful job of telling all the story I needed told without things feeling too cramped. His panel design is very dynamic, and it really keeps the book from feeling claustrophobic.

So what's next for you in comics? Are you going to keep returning to these DC digital books? Do some more "Arrow" tie-ins? Something else entirely?

It's funny -- I've finally carved the space in my schedule for a monthly book. Back when I was doing comics with much more regularity, I could do a few monthly books. I don't have the bandwidth for that now, but I'd really like to get one book that I could pour my heart and soul into. I feel like I've learned a lot in the past two years about my comic book writing. I'm particularly proud of my "Adventures of Superman" story, and now this "Legends of the Dark Knight" tale. I feel like my craft has come up a level. Now I'm just waiting for a call from an editor, and I'll be off to the races.

Guggenheim's "Legends of the Dark Knight" story kicks off Tuesday, November 19.