Batman: The Long Halloween

The project was sparked when group editor Archie Goodwin approached Jeph Loeb and Tim Sale at the San Diego Comic Convention and asked if the two of them wanted to do more Batman work.[3]

Jeph Loeb has stated that the genesis of the story was influenced by writer Mark Waid, who, when told that Loeb was working on a story set in the Year One continuity, suggested focusing on Harvey Dent's years prior to becoming Two-Face, as that had not been depicted in depth since the original Year One story.[4]

At a wedding in June, Gotham City mob boss Carmine "The Roman" Falcone tries to pressure Bruce Wayne to help launder money, but Bruce refuses. Bruce leaves the party with his quasi-girlfriend Selina Kyle, but they find Gotham District Attorney Harvey Dent, who has been beaten by some of the Falcone mob, and help him escape. Bruce, as Batman, investigates Falcone's penthouse, but finds Catwoman investigating as well. Batman is called by the Bat-Signal to meet with Dent and police Captain Jim Gordon. The three agree to enter a pact to end Falcone's reign, bending but never breaking the law.

Bruce, on the board of the Gotham City Bank, uses his sway and his influence as Batman to oust the current president, Richard Daniel, and take over as to rid the bank of the Falcone money it has. Falcone orders his nephew Johnny Viti to fix the problem; Viti assassinates Daniel. Viti is killed on Halloween by an unknown assailant, leaving behind an untraceable pistol, a nipple from a baby bottle used as a crude silencer, and a jack-o-lantern. Batman, Gordon and Dent discuss the murder when Batman sees Catwoman lurking nearby. She leads Batman to a warehouse where Falcone has been forced to stash his money, over $20 million. Batman and Dent agree to set fire to the warehouse and destroy the money. Falcone hires "The Irish", a gang of hitmen, to get revenge on Dent, who has been promoted to district attorney. The Irish destroy his home, though Dent and his wife Gilda survive. On Thanksgiving, the Irish are killed by an unknown agent, but leaving the same type of pistol and silencer behind along with a Thanksgiving decoration. Milos Grappa, Falcone's bodyguard, is killed in a similar manner on Christmas. The unknown assailant is given the name "Holiday" and believed to be a Falcone rival.

On New Year's Eve, Batman stops the Joker from using deadly laughing gas to kill everyone in Gotham Square, as the Joker believes Holiday will be among them, and asserts that there is not enough room for two homicidal maniacs. Meanwhile, Dent's assistant Vernon Fields finds evidence linking Falcone to Wayne. Aboard the Falcone yacht, Falcone's son Alberto is killed by Holiday and pushed overboard on New Year's Eve, his body apparently recovered on Little Christmas. Over the next few months, Holiday's targets change to that of the Maronis, a rival crime gang in Gotham. A war between the Falcones and Maronis breaks out, and Falcone is forced to turn to Gotham's "freaks" like the Riddler and Poison Ivy to hold his ground. Poison Ivy, per Falcone's instructions, successfully ensnares Bruce Wayne on Valentine's Day, coercing him into laundering money for Falcone. This unintentionally takes Batman out of the equation. It is not until Saint Patrick's Day when Selina Kyle is able to figure out what has happened to him and, as Catwoman, free him from Poison Ivy's clutches. And it is the Riddler who becomes the first target that is spared by Holiday on April Fool's Day, which Batman comes to suspect is a message from Holiday to show Falcone that he knows what Falcone is up to and wants to destroy him.

Meanwhile, the pistols left behind by Holiday and the bullets gleaned from Holiday's victims are traced to a Chinatown neighborhood, but they find the gunmaker dead as Holiday's victim on Mother's Day. On the following day, Dent follows up from Vernon's investigation and has Bruce arrested, claiming that as Bruce's father Thomas Wayne saved Falcone's life after he was shot, that Bruce is loyal to the Falcones. Bruce's butler Alfred testifies that Thomas' report never came to light due to police corruption, embarrassing the prosecution and declaring Bruce innocent—especially in light of the murder of the Gotham City coroner on Independence Day.

Sal Maroni, having been captured earlier, offers to testify against Falcone after his father was killed on Father's Day. During the trial, he throws a vial of acid, given to him by Vernon while in transit to the courtroom, at Dent, disfiguring half of Dent's face. Dent is rushed to a hospital, but stabs his surgeon and escapes to the sewers, calming Solomon Grundy when he encounters him. Gordon deduces Dent may be Holiday, but Batman refuses to believe it until he can talk to Dent himself. After Falcone's sister Carla Vitti is murdered on Falcone's birthday in August and her body found in the Coroner's Office, Batman ends up questioning Julian Gregory Day, the Calendar Man, on where to find Dent. Day suggests since that it is Labor Day, that Holiday will try to kill Maroni. Batman stages a plan with Gordon to move Maroni, giving Holiday the means and opportunity. During the transfer, Holiday appears and manages to shoot Maroni, but Batman, having disguised himself as one of the security guards, is able to stop him. Holiday is then unmasked as Alberto Falcone, son of Carmine Falcone who had staged his death.

On Halloween, Dent resurfaces as Two-Face; he releases the prisoners from Arkham based on a coin flip, seeks out and kills both Falcone and Vernon despite Batman's attempts to stop him. Falcone's daughter Sofia is also killed but not at the hands of Two-Face. Instead, her death is an accident caused by Catwoman. His revenge complete, Two-Face turns himself in to Gordon and Batman, but tells them that there were two Holiday killers. Gordon is confused as Alberto confessed to all the killings and has already been sentenced to death. While Batman dismisses Two-Face's statement due to his obsession with the number two, Batman does point out that since Two-Face killed Falcone and the last of his collaborators on Halloween, Two-Face is technically Holiday. While Two-Face is imprisoned within Arkham along with the recaptured prisoners, Alberto is able to delay his execution on the basis of insanity.

Months later on Christmas Eve, Gilda is packing boxes to move away from Gotham, but takes one box to her furnace, containing a pistol, a hat and what appears to be her husband's clothing. As she burns the items, she thinks about how she took it upon herself to start the Holiday killings to try to end Falcone's hold on Gotham and reduce her husband's workload so that they would have time together. She has the wild suspicion that Alberto was lying, instead choosing to believe that Dent himself had taken up the killings on New Year's Eve and that the two were finally working together, sharing secrets together. Nevertheless, she is content with Alberto as their scapegoat, knowing the authorities are unable of finding the other Holiday killer without Dent on their side. Knowing that Dent is not really insane and can be cured, Gilda states she still believes in Harvey Dent.

Batman: The Long Halloween has received widespread critical acclaim and is praised as one of the definitive Batman stories to date due to Jeph Loeb's involving storyline and Tim Sale's dark, moody art.

Hilary Goldstein of IGN Comics praised Loeb's story as "tight, engrossing, and intelligent writing that never betrays the characters", adding that he "mixes Batman and Bruce Wayne's lives as well as anyone has, and brilliantly demonstrates the bond of brotherhood shared by Batman, Jim Gordon and then District Attorney Harvey Dent."[5] Goldstein later ranked The Long Halloween #4 on a list of the 25 best Batman graphic novels.[6]

Yannick Belzil of The 11th Hour said that "Jeph Loeb has crafted a story that is unique to the characters. It's a complex murder mystery, but it's also a Batman story." Belzil added: "Buoyed by a film noir-ish plot that features a Gothic twist on the gangster/murder mystery plot, terrific character-based subplots, and beautiful, cinematic art, [The Long Halloween is] an addition to your collection that you won't regret."[7]