Written by Jeph Loeb
Penciled by Tim Sale
Inked by Tim Sale
Colored by Gregory Wright
Published by DC Comics
Not only does Batman boast one of the greatest rogues’ galleries in all of comics, his villains have become so iconic that his rogues’ gallery rivals that of Andrew Jackson’s, Axl Rose’s, and that of the 1978 New York Yankees. The villains that torment the Dark Knight are so impressive that any one of them can carry a compelling story by themselves. However, something as monumental as the heavy hitters like Joker, Catwoman, Penguin, and eventually Two-Face all coming together during the events of The Long Halloween is only a small part of that story’s overall success. There are so many things that make The Long Halloween the seminal Batman story that it becomes impossible to try and isolate one specific facet as being solely responsible for the success of the storyline.
What immediately separates The Long Halloween from other Batman stories, is that like The Killing Joke, Batman is more of a supporting character. Although Batman is obviously the protagonist, the main character is Harvey Dent, the man who because of the events of the story becomes the Freudian villain Two-Face. Whereas The Killing Joke presented a possible origin story for the Joker, in The Long Halloween, writer Jeph Loeb and artist Tim Sale mastermind the definitive and tragically predestined fate that would befall Harvey Dent.
Literally, metaphorically, and emotionally, The Long Halloween begins and ends with Harvey Dent. Readers first meet the hapless, yet dedicated Harvey Dent as he is being accosted by mob goons. As readers learn more about him, and the tribulations that he has gone through, it becomes impossible not to sympathize and support him. From his abusive childhood at the hands of his father, the repeated attempts on his life, and impotence caused by his stressful job as Gotham’s district attorney, their sole beacon of hope, their Apollo, Harvey Dent becomes the focal point of The Long Halloween. Without such a strong emotional resonance that Loeb forges between the reader and Harvey Dent, this iconic story would have very easily fallen apart. By the end of the story, Harvey Dent has been transformed into the psychopathic Two-Face who gives in to lawlessness and chaos, a being who functions as the id to Dent’s superego.
The battle for Gotham would be waged in the soul of Harvey Dent.
The loss of Harvey Dent as a figure of justice, and as a crusader doesn’t go unannounced by Gotham’s other crime fighters, Batman and Jim Gordon. Up until their final conversation, readers are constantly presented with the age old quandary of why bad things happen to good people. However, Gordon’s last words to Batman raises an even more poignant question: “Was toppling the mob worth losing Harvey Dent?”. This question, along with the final twist of this murder mystery will stay with readers long after finishing the story and even after multiple reads.
The unraveling of Dent’s sanity, which runs parallel to, and often intersects the Holiday Killings (murders that are being committed on holidays) serve as the backbone of the story. Underneath the surface however, another battle is being waged between the Mafia, the traditional criminals of Gotham, and the Freaks, the new breed of costumed criminals such as the Joker, Poison Ivy, and Catwoman. The continuity of The Long Halloween is perfect because it positions itself right at the tipping point of this struggle, right where the mob starts to lose control and the Freaks begin to claim Gotham as their own. As Gotham’s descent into a breeding ground for crazier, wilder criminals occurs, so too does Two-Face’s emergence as a tether between the two worlds become more pronounced. Within this magnificent story, Jeph Loeb manages to weave three interweaving crises: the internal battle for Dent’s soul, tracking down the Holiday killer, and the war between the Mafia and the Freaks. The theme of all of these wars is to leave yourself behind as Gotham is changing from what it once was to the city that readers are more accustomed to. In Loeb’s magnum opus, he takes readers on a ride and shows them how the Gotham City in Batman: Year One which belonged to the mob, became the Gotham City of Arkham Asylum: A Serious House on Serious Earth where the Freaks have already laid their claim.
When it comes to storytelling and crime fighting, there are two versions of Batman; there’s Batman the detective, the one who fights the mob and your average two-bit criminal. This is the Batman who loves Catwoman. There’s also Batman the superhero, the one who stops the Joker from poisoning the water reservoir, and the one who has to prove his innocence when Man-Bat attacks. This is the Batman who’s in love with Talia Al Ghul. Because of the shifting balance of power between the mob and the costumed villains, Jeph Loeb manages to rectify both versions of Batman into one coherent character who was initially after the mob, but is now equipped to handle the supervillains. Loeb’s Batman is unstoppable but not infallible; he is more than a man, but not superhuman, as he can stop the Joker from gassing the city on New Year’s Eve, yet he is susceptible to Poison Ivy’s seduction. More importantly however, Batman can stop the Holiday Killings without figuring out who the killer is. Loeb’s Batman is one who will win, but not without a cost. The ultimate cost being the loss of Harvey Dent, one of the last good men in Gotham.
One of the hidden gems of the story is Harvey’s loyal and eternally loving wife, Gilda Dent, the Penelope to his Odysseus. She is the lone voice of sanity, looking in from the outside as she too is slowly warped by the twisted world of Gotham City. While Harvey’s story is that of a fall from grace, Gilda’s is one of innocence lost. With such a wealth of material to springboard from, it’s one of the biggest shames in modern comic storytelling that no subsequent writer has adequately examined the relationship between Harvey and Gilda Dent.
The Long Halloween is not only the greatest Batman story ever written, it’s also the most perfect, the most complete portrait of Batman and the world in which he lives and operates in. There’s so much going on in the story, so much plot, so much intrigue, so many characters, and so many memorable moments. However, because of the craftsmanship that went into The Long Halloween, it never feels bloated or overwhelming. Every plot point is set up perfectly and is then paid off nicely, and every pertinent character gets their moment in the sun. Of particular note is the altercation between Joker and Harvey Dent as the former breaks into the latter’s home. What Loeb seems to understand is that both characters occupy completely antithetical roles. The Joker is pure chaos and sociopathy. Two-Face was borne from repressed emotion and relies on his coin to make decisions for him as he feels the weight of both outcomes equally on him, so he has to defer his judgement. The war between Harvey Dent and Two-Face is still being waged which is why he has to use his coin to make decisions.
In relation to Batman, Joker is the ultimate, the archfiend who is Batman’s equal and opposite. By contrast, Two-Face is Batman’s biggest failure. The monster known as Two-Face serves as a constant reminder of Batman’s inability to save one of his allies and prevent Dent’s madness from becoming all enveloping. Two-Face was born because Batman failed. He failed to trust Harvey Dent during the Holiday killings, and then he failed to stop mob boss Sal Maroni from hurling acid in Dent’s face. That failure will haunt Batman forever in the form of Two-Face.
“The Long Halloween is more than a comic book. It’s an epic tragedy”. -Christopher Nolan
For someone who had never read, nor even heard of Batman before, The Long Halloween is the best introduction to the Caped Crusader. Unlike Batman: Year One or The Dark Knight Returns, this masterpiece by Jeph Loeb and Tim Sale is an epic. It’s not as boring as Year One nor is it as retrospectively over-the-top and self-gratifying as TDKR. Everything that readers want in a Batman comic is found within the pages of The Long Halloween: an intriguing murder mystery, justified appearances by memorable villains, elements of The Godfather, character examinations, and a strong emotional core centered on one of Batman’s most important villain. From the Vito Corleone inspired Carmine Falcone to the Joker reciting lines from “How the Grinch Stole Christmas” as he breaks into a house, The Long Halloween presents Batman and his accompanying universe at its most concentrated and seamless. Simply put, The Long Halloween is a perfect comic. It should be at the very top of any Batman fan’s “Must Read” list, and for those who’ve already read it, The Long Halloween deserves to be read and enjoyed again and again.
 If you don’t believe me, just read Hush, written by Jeph Loeb ironically enough.