Jeph Loeb and Tim Sale got the attention of Batman fans with three Halloween tales (available in the single-volume Batman: Haunted Knight—The Legends of the Dark Knight Halloween Specials). Not long thereafter, then-DC-editor Archie Goodwin suggested they collaborate on a Batman story that would pick up the gangsters from Frank Miller's Batman: Year One. The result was Batman: The Long Halloween (1996-1997), an intriguing blend of superhero stories and film noir.
The Long Halloween may be most distinguished for its elaboration on the character of Harvey Dent. The story picks up not long after the events of Batman: Year One. Batman is a hero still met with some skepticism by the powers that be, though he has an ally in James Gordon and the tentative support of District Attorney Dent. Determined to put an end to the reign of crime boss Carmine "The Roman" Falcone (created by Miller in Year One), Batman, Gordon, and Dent take a rooftop meeting by night. Pledging to not rest until they bust Falcone—and agreeing to bend but not break the law—the threesome embark on a journey of grim duty and uneasy faith.
The journey lasts over a year, as they not only work against Falcone but attempt to unmask a mysterious serial killer called Holiday. Once a month, on a notable holiday, the killer offs one or more members of Falcone's crime syndicate. As in Year One, Gordon's dedication strains his relationship with wife Barbara; Loeb introduces Gilda, Dent's wife, who similarly laments the absences and danger inherent in her husband's work. Batman mostly gets down to business, but his character does come into relief when he's infected by the Scarecrow's fear toxin on Mother's Day, revisiting his parents' murder at a rather inconvenient moment.
Surely, Loeb's story is not as sophisticated, mature, or disciplined as Miller's story, but it is a heck of a lot of fun. Admittedly, Loeb's insistence on fleeting cameos by rogues gallery villains strains the believable bounds of the story, but then again Loeb's fanboy spirit is infectious (I mean, who doesn't love Solomon Grundy?). Some episodes legitimately weave in famous baddies—among them Calendar Man (an appropriate choice), the Joker, Poison Ivy, and Scarecrow—but the story's at its best when dealing with its core characters: Batman, Gordon, Dent, and the Falcones. Though Loeb works within a milieu familiar to fans of The Godfather and Scorsese's mob pictures, it most closely resembles The Sopranos in its soap-operatic relationships among male and female family members; to Loeb's credit, The Long Halloween anticipates The Sopranos, which hit the airwaves a few years later.
Sale's art strikingly lays claim to Gotham's finest and funkiest in spacious, uncluttered layouts. Sale's panels are never tiny and often huge, including some jaw-dropping splash pages. Loeb and Sale's habitually stubbly Batman is the opposite of Miller and David Mazzucchelli's human-sized hero. This Batman is monstrous and muscularly rippled, with a billowing cape and ability that verges on the supernatural. Sale suits his depiction of Batman to the moment and the mood, employing noirish restraint in more intimate scenes and more dynamic strokes for much of the superheroic action. Gregory Wright's coloring work is excellent (the murder scenes slip into shadowy black and white).
The story culminates dramatically in the reinvisioned origin of Two-Face. Loeb treats the character of Dent well, wisely tainting him with moral uncertainty in his "before" stage (and cleverly allowing him to talk to himself) to make his "after" stage as Two-Face more believable (think Anakin Skywalker). The resolution of the Holiday whodunnit pulls an awkward, hard-to-swallow bait-and-switch, and the criticism that "the World's Greatest Detective" allows a killer to operate for over a year is a fair one. Though the story occasionally resorts to gimmicky stunt tactics, The Long Halloween is a sprawling and artful page-turner that's well worth a read.
[The collected edition includes an introduction by Loeb, which pays tribute to editor Archie Goodwin (and gives props to Frank Miller), as well as explaining the origins of the story.]