The Modern Age of Comics was in full force by the 1990s. Gone was the fantastical whimsy of the Golden and Silver Age and in its place, a gritty realism, that built upon what the Bronze Age has established in the 1970s. The heroes and their stories were more complex, the themes were more mature and writers were becoming bolder in their creative direction. The 90s were characterised by landmark comic events such as The Death of Superman and Emerald Twilight , challenging readers’ perception of their favourite characters and interpreting them in a (relatively more) realistic light. In some instances, heroes were acting like villains, with antiheroes becoming cult favourites like Spawn and Deadpool, using whatever means necessary to get the job done.
Despite DC's most popular character, Batman being crippled by Bane in 1993’s Knightfall , it would be another prominent 90s story that focused on the Dark Knight's crime solving skills and why he earned the moniker, the "World's Greatest Detective." A long year awaited the Caped Crusader, wherein a serial killer with a unique method would be loose upon Gotham City.
A serial killer known as "Holiday" (nicknamed for killing on holidays) begins to terrorise Gotham, murdering gang members and threatening to instigate a war within the criminal underworld. Batman teams up with Commissioner Jim Gordon and District Attorney Harvey Dent to uncover the identity of the killer before the city tears itself apart. Only the villain known as Calendar Man may provide a clue as to Holiday's whereabouts.
Batman: The Long Halloween , a 13 issue limited series, published between 1996-1997, takes place during Batman's early years as a crimefighter, set after Frank Miller's Batman: Year One , evolving the rogue’s gallery from mobsters to supervillains. After having worked on the Batman comics, DC group editor Archie Goodwin approached writer/artist team Jeph Loeb (current Executive Vice President for Marvel Television) and Tim Sale to continue working on the character. Fellow writer Mark Waid gave Loeb the idea to set the story within the Year One continuity and focus on Harvey Dent, prior to his transformation into Two-Face as that hadn't been explored since the original Year One comic.
The Long Halloween opens up as Bruce Wayne, along with Selina Kyle are attending a wedding. Mob boss Carmine "The Roman" Falcone tries to persuade Wayne into laundering money with him, however, he refuses. As Wayne leaves the party, he finds District Attorney Harvey Dent, who has been beaten up by some of Falcone’s goons. As Batman, he later goes to investigate Falcone’s penthouse, encountering Catwoman and giving chase. Batman ends the pursuit to answer the bat signal, where he, Commissioner Jim Gordon and Dent enter into a pact to end Falcone’s empire, by bending the rules, but never breaking them. On Halloween night, Falcone’s nephew, Johnny Vitti, is assassinated by an unknown assailant, leaving behind the murder weapon. As Batman, Dent and Gordon discuss the murder, Catwoman gives them information that leads the trio to a warehouse where Falcone has stockpiled $20 million in cash. Batman and Dent set fire to the warehouse, thus destroying the money. After an unsuccessful assassination attempt on Dent by Falcone, the gang Falcone hired to carry out the hit are murdered on Thanksgiving, while Falcone's bodyguard is killed on Christmas. The media dub the killer, "Holiday", for carrying out the murders on holidays. On New Year's Eve, Batman is forced to put his investigation on hold in order to stop the Joker, who wants to kill Holiday (by murdering everyone in Gotham Square) for stealing his thunder, while Falcone’s son, Alberto is shot by Holiday.
Over the next several months, Holiday targets members of Sal Maroni’s gang, which ignites a huge gang war between the rival criminal organisations, with Falcone having to employ the services of the Riddler and Poison Ivy to stabilise his operation. Meanwhile, Wayne is later arrested, after Dent investigates a possible connection between the billionaire and Falcone. However, Wayne is set free after the trial rules in his favour and the city's long history of police corruption is brought to light. Batman later finds the Riddler, whom Holiday left alive on April Fools' Day, as Riddler explains that Falcone hired him to found out who Holiday was, but was fired for being unsuccessful. Batman deduces that Riddler was left alive to spread the word that Falcone was looking for Holiday. As Sal Maroni testifies against Falcone, Maroni flings acid at Dent, horribly disfiguring one side of his face and is rushed to hospital, but later escapes. Gordon comes to the conclusion that Dent is Holiday, however, Batman refuses to believe that, while Gordon wants to hear the truth from Dent himself. Given the killer’s method for attacking on holidays, Batman visits Calendar Man in Arkham Asylum, where he suggests that it being a holiday, Hoilday is probably going to kill Maroni. As Maroni is being moved to a new cell, Holiday appears and kills him. The killer is revealed as Alberto Falcone, who faked his death and is taken into custody by Batman (disguised as a bodyguard). On Halloween, Dent (now Two-Face) releases all the Arkham inmates and Falcone is ambushed in his penthouse by the escapees. Batman arrives, but is too late to stop Two-Face from killing Falcone as well as his former assistant for helping Maroni scar him. Two-Face turns himself in, informing Batman and Gordon that there were two Holiday killers.
Alberto confesses to committing all the Holiday murders, while it is generally believed that Two-Face was the second killer, since he killed Falcone on Halloween. On Christmas Eve, Gilda Dent (Harvey's wife) packs for her move away from Gotham, describing that she had read her husband's case files and that she was responsible for the Holiday killings, in an attempt to stop Falcone’s reign, to lighten Dent’s workload so the couple could have a child. The comic ends with Gilda holding out hope that Dent will be cured because she believes in him.
Batman: The Long Halloween is seen as one of the definitive Batman stories, thanks to an intriguing storyline and moody artwork. A year-long mystery, Batman struggles to find the elusive Holiday, who is systematically destroying Gotham's criminal underworld, bringing the city to its knees in the process. While being labelled the "World's Greatest Detective", Batman doesn't actually solve the case, as the killer comes forward to confess his crimes, leaving the Dark Knight interrogating various individuals connected to the murder. The Long Halloween sets into motion several key events such as Harvey Dent's transformation into Two-Face (Dent becomes increasingly cavalier towards the crime bosses, prior to the acid incident), with Dent beginning to form a grudge towards the rich and famous like Bruce Wayne from walking away from a trial. Dent’s arc was used as inspiration for the movie, The Dark Knight and the phrase, "I believe in Harvey Dent" (a campaign slogan used in the film) has its origins in this comic. Furthermore, The Long Halloween would mark the transition for the rogues gallery from crime bosses to full-blown super villains (thanks to Holiday murdering all the crime lords), with the Joker episode further establishing Batman’s reputation and the escalating danger Gotham would come to ensure. The final twist makes for a captivating reveal, though it becomes a little unclear as to when each of the killers took over from the other (there are technically three killers: Gilda, Harvey Dent and Alberto Falcone). Batman: The Long Halloween was followed by a sequel, Batman: Dark Victory in 1999, introducing Dick Grayson to the Bat-Family. The Long Halloween is a compelling story and well worth the read, with an alluring mystery at its core, testing Batman's detective skills to their limits.