Jeph Loeb Talks Last Halloween: Honoring Tim Sale, The Penguin, and more

Jeph Loeb and Tim Sale’s Batman: The Long Halloween is considered one of the greatest Batman stories ever told. However, with Tim’s passing in 2022, plans for a future installment of the series were put on hold. In 2024, Loeb will team up with a series of talented artists for Batman: The Last Halloween, the final chapter of the original comic. We spoke to Loeb about honoring Sale with the comic, the original plan for Last Halloween, and the influence the original story had. Check out our conversation below.

“Gotham City learns to fear Halloween once more as a terrible event threatens to destroy Jim Gordon's life and puts Batman and Robin's teamwork to the test more than ever before. In a city of liars, masked vigilantes, and criminals... can anyone be trusted?”

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What was the original plan for the comic, and how did that change with Tim's passing?

The original plan was to do a ten-part murder mystery that would tie off the loose ends from The Long Halloween and from Dark Victory and from Catwoman in Rome. And even things that I had planted in the first three Halloween specials that I thought, you know, it'd be cool if we could tie it all together. And Tim and I worked on a ten-part outline of what it was going to be. And I wrote the first two scripts with Tim in mind because I write very specifically for a very specific artist.

He started three pages, which are very rough — they're almost sketches. DC is going to re-release the special on September 8th, which was the last thing that we did. The special now becomes the prologue for the story. So it's the last Halloween zero. And it's super cool. It's got ten pages of interviews and artwork from Tim. Those three pages are in there to show that this is where we were going.

And then Tim was gone. And you can't explain it. And so I took it, and I put it in a drawer and said, well, that's not something I'm ever going to touch. And about a year went by. And Richard Starkings, our letterer and our designer, and our inspiration in so many ways, and Mark Chiarello, who was for 20 years the art director at DC and also our editor on Dark Victory. We just started talking about what we should do with Last Halloween. Should we just sort of let it go? And they managed to sort of get me to think about it differently, to think about it instead of something that I'm doing without Tim. Maybe it was something that we could do for Tim.

And so I liked that idea. And then Chiarello came up with this image that's still in my head, which is, he goes, just imagine if we could get all these artists together to do this. And when it gets collected, imagine Tim sitting in a rocking chair on Pa Kent's porch in some mythological Smallville, and he's looking through it, and he's just smiling because it's all the artists that he loves. And that was the key. Like, instead of trying to find people who drew like Tim or trying to get superstar artists that are going to do this for Tim, let's find people who were Tim's inspirations, people that Tim would say to me constantly, “Look at this, this guy's super cool.” And sometimes I knew them, and sometimes I didn't know them, and he taught me about them.

How do you begin that process of finding the artists?

We made a list together, and I started asking. And it is a testament to Tim that all ten artists, like, as soon as I said we're doing this thing with Tim, they were like, “I'm in.” And I was like, well, you should kind of hear what it is. And they would go, “I'm in, whatever it is. I'll stop whatever I'm working on.”

And so, you know, it starts with Eduardo Risso from 100 Bullets. Super cool. The legendary Klaus Janson. Mark Chiarello is doing interior work — Mark is a brilliant illustrator. Cliff Chang, who I adore. Bill Sienkiewicz is doing interiors… He was one of the first people to do it. And it's so gorgeous. Dave Johnson, who hardly ever does interior work now and just beautiful covers, and Becky Cloonan, who just walked out with every single Eisner that there is. Chris Samnee, I just adore. And then Matteo Scalera, who did One Bad Day with Mr. Freeze, is doing a wrap-up of it because I needed somebody who could do all of the characters. And Matteo is just capable of doing all of that.

Then we're doing multiple covers, but they serve a purpose in that the A cover is all pieces of Tim Sale artwork that no one has ever seen.

And so it now became a different thing. It became a gift from Tim to me in the sense that these are people that I've never worked with before. So I had to sort of relearn how to tell a story that was not for Tim but worked towards their strengths. But by the same token, they all have; they were all inspired largely by the same people. I told the artists, “I want it to look like your work. I don't want you to be drawing like Tim, but I do want you to use Tim's designs. So it is Tim's Batman. It is Tim's Catwoman. It has to all fit together with the other stuff.

What is it like to see the influence the original stories have had, especially on the kind of continuity and tone of what Batman is and what that world is?

It was so incredibly kind because I think, as a fellow geek, one of the frustrations is that directors and writers don't give enough credit to the source material and to the people who really got them interested in the first place. And with Matt Reeves, who did the last Batman story, it was to the point where, like, I got embarrassed [laughs]. I was like, guys, you don't have to talk about me like I appreciate it. And please talk about Tim all you want. But, you know, just part of the reason why I wanted to revisit these characters is that they do have such an impact.

In this new Penguin series, the main antagonist is Sofia Falcone. Every single time I see a trailer or anything of it, I'm just like, how cool is that? Because I also work on that side of the business, too. So, seeing all of those things mixed together, I'm honored. That is the best way I can answer it. 

What makes the dynamic between Harvey Dent and Batman so special?

They are very much alike in so many ways. I mean, it's a cliche to say, but they are two sides of the same coin.

You know, the idea is that, in many ways, Harvey was going to be Gotham's white knight. I mean, that's how they saw him. And when he got his face destroyed, and Two-Face emerged, that's who Harvey always was. He just needed to get out.

For Bruce, he went the other way. His life was completely destroyed, and he decided, “I'm going to make this promise to rid the evil of the city that took my parents’s life.” So I think that what you have is such a great dynamic of someone who is determined to clean up the city and another guy who's determined to clean up the city, but not the way that Batman would do it. Like he's doing it with two .45s and as many of the freaks as possible.

When people ask me what's the difference between Long Halloween and the last Halloween, I tell them that Long Halloween was really a story about how the freaks took the city from organized crime. And then the Last Halloween is organized crime saying, “yeah, we never really went away. So we're going to have to have a conversation about this.”

Speaking of the freaks, one thing I really love about this entire series is that Solomon Grundy and Calendar Man have appeared in every story so far. What makes them such interesting villains, and how do they fit in a story that’s more grounded?

I've always felt that there aren't any really ridiculous villains. It's just how you use them.

I will say that when we started with Calendar Man, you know, Tim said to me, “Wait, are we doing this guy that's got like pages hanging off of him?” I said, “Think Hannibal Lecter, let's go in that direction.” And Grundy, to me, was so horrific, particularly the way that he drew him. And so there's that. We also had fun with the Mad Hatter.

I learned something from this story. Like I used to always say — now Tom King has proved me wrong — but there's never really been a good Penguin story. And I've used Penguin, so I include myself in that. But, you know, once I had Klaus Janson, I was sort of like, oh, this is cool. And absolutely, the movie has proved that if you make him a crime boss, he's a really interesting character.

I just try to find characters that maybe you don't know. And if you twist them a little bit, always towards madness, you're going to find some fun there.

Obviously, the Long Halloween introduced the killer holiday. And we've seen kind of different iterations of what Holiday could be. Are we going to see more of that name show up in this book?

Let me just say that I don't know how to tell the story that wraps it all up without involving a Holiday. That's the best way that I can answer. 

What is Batman and Robin’s dynamic going to look like in this book?

Well, Dark Victory was really about Robin's origin, and it ended with him becoming Robin. So now I wanted to tell a story that is, OK, now you've been Robin for a while. I let the continuity mavens try to figure out how this could all take place in Year One. Tim always drew him like he was eight. And I was like,
“he’s not eight. He's 10. Like, I understand you don't have kids, but you draw him like he's a tiny person.” And so what I had to say to everybody was not to draw him the way that Tim drew him.

He's 13 years old. He's River Phoenix and Stand By Me. That's how I see him. And he has that kind of tough guy image. I mean, the thing about Dick that I love is that, unlike all the other Robins, Dick came from a world of action and adventure. Like he loves being Robin, he's an acrobat. He's out there for the show. And it's obviously something that he and Batman don't always agree on because Batman is continually looking at him, going, “This is not a game. This is not this is not a circus. Because he can't actually say, “Dick, what I'm afraid of is that you're going to die.”

So, like, it is a very unique father/son relationship that I completely adore, right? I mean, when you see Cliff Chang's issue four, which focuses more on Robin than on Batman, you'll really get a sense as to what that relationship is like and how Dick deals with being in this world.

Thanks so much to Jeph Loeb for taking the time to do this interview! Batman: The Last Halloween releases on September 25th, 2024.