With The Batman, The Penguin, and Christopher Nolan's Dark Knight trilogy all drawing ideas from it, The Long Halloween has become the most influential Batman comic ever

If you ask comic book fans what the most influential Batman stories are, they will probably cite Frank Miller's Batman: Year One or The Dark Knight Returns . They're not wrong, necessarily, but hands down the single most influential comic on modern Batman movies and TV shows – particularly HBO's currently airing The Penguin – is Jeph Loeb and Tim Sale's The Long Halloween and its sequels.

Published by DC in 1996 and 1997, the 13-issue series charted Batman's investigation of Holiday, a killer who murders people on, well, holidays. It was itself a sequel to three Halloween specials Loeb and Sale had published in Legends of the Dark Knight (which are collected as Batman: Haunted Knight) and was followed by two sequels: Batman: Dark Victory, and Catwoman: When in Rome. Though Sale passed away in 2022, Loeb worked out one final story with the artist, and the first issue of the closing chapter of this "trilogy" was published last week by DC Comics under the title Batman: The Long Halloween - The Last Halloween .

Spoilers for Batman: The Long Halloween

Part of what makes The Long Halloween and its sequels so influential is the period where it's set in Batman continuity. Batman: Year One by Miller and David Mazzucchelli presents a younger Batman just being introduced to Gotham, and it ends with a tease of the Joker, something that Christopher Nolan's Batman Begins directly picked up on. However, the book is mostly concerned with Batman's relationship with Jim Gordon, and the crime families of Gotham; the Falcones in particular.

Loeb and Sale picked up the ball Miller and Mazzuchelli left behind and ran with it, presenting a canonical Year Two for Batman that charted the fall of the mobs and the rise of the freaks in Gotham City. Most of the plot of The Long Halloween involves Holiday targeting members of the Falcone and Maroni crime families, picking them off one by one. Meanwhile, villains like Riddler, Poison Ivy, and more start popping up in the city… And as the Falcones recruit them to help out against Holiday, the mantle of power begins to pass from the old-school mobs to the new-school supervillains, with Holiday bridging the gap… He's one of the freaks but also is revealed to be Alberto Falcone, the scion of the Faclone crime family. His reveal as the killer is, essentially, the death knell for the mobs. It's that fraught tension that powers the series and has made it a classic, and it's that same tension that has enamored countless film and TV makers.

There's no better example of this transition than one of the main characters of The Long Halloween: Harvey Dent. He's an ally of Batman's, a DA trying to do the right thing in Gotham. But when he is caught in the middle of the spiraling gang war between the Falcones and Maronis, he ends up having his face hideously scarred. And thus he becomes Two-Face, one of the very freaks that has been causing the mob families to run around like chickens with their heads cut off in the first place.

Anyone with a passing familiarity with Nolan's Batman movies, Matt Reeves' The Batman , The Penguin, or even Fox's Gotham (particularly Season 4) can see the DNA right on the surface. While Batman Begins used elements of The Long Halloween, the characterization of Harvey Dent, Jim Gordon, and Batman's relationship in The Dark Knight is straight from the comic book series. Similarly, The Batman wears its influences on its sleeve… The whole plot of the movie sets Batman in year two of his career and shows the death of Carmine Falcone (John Turturro) thanks to the machinations of The Riddler. And not for nothing, but the opening of the movie is set on – when else? – Halloween.

Spoilers for Batman: Dark Victory

The Penguin picks up right from there, with the Falcones and Maronis in disarray… And more importantly the return of Sofia Falcone (Cristin Milioti), a key figure in The Long Halloween who is later revealed to be Dark Victory's Hangman killer. And what is Sofia known as in The Penguin when she's released from Arkham Asylum? The Hangman.

It's no accident that The Long Halloween cycle is so influential on The Batman because Matt Reeves was literally a student of Jeph Loeb's. Reeves posted as much on X (formerly Twitter) back in 2018, noting that Loeb was one of his screenwriting teachers at USC. But funnily enough, he didn't make the connection until he started researching for The Batman.

"It's so weird because I didn't know till I did all of this deep dive that it was literally my screenwriting teacher from USC – the person who told me that I should become a writer – Jeph Loeb, who wrote those stories," Reeves said in an interview with EW in 2022. "He was very responsible for me pursuing that because when I went to film school, I was very set on being a director. I'd always written what I was doing as a kid and when I was making short films when I was young because I thought these are the means to get to make a movie. And I never really separated the two. And when I was in [Loeb's] screenwriting class, he said, 'You have to continue pursuing this because this is something I feel you can do.' When I started going through all the comics and I saw that he'd written [them], I was like, 'This is crazy.' And then I loved it."

So if you're hunting for clues on what might happen next on The Penguin, where Reeves might go in The Batman Part II , or simply want to know what Gotham City was like before its monthly Joker attacks then look no further than The Long Halloween, Dark Victory, and the currently running The Last Halloween – a body of work that continues to influence the future of the Dark Knight's onscreen adventures, while looking back to his past.

Batman: The Long Halloween - The Last Halloween #1 is out now from DC. The Penguin is streaming now on Sky and NOW in the UK and on HBO in the US.