Written by Dennis O'Neil, illustrated by Ed Hannigan. DC launched the Legends of the Dark Knight series in 1989, which proved to be a very popular year for the Caped Crusader. The series was to be a standalone publication, not necessarily linked to the continuities followed by Detective Comics and Batman, and was to feature a constantly-rotating roster of writers and artists. The first arc is "Shaman", written by the legendary Dennis O'Neil and drawn by Ed Hannigan (my last name!), and it set the bar high for an incredible series to come. A pseudo-origin story that neither negates nor is contingent upon Frank Miller's "Year One", "Shaman" opens with a younger Bruce Wayne training with a famed bounty hunter in the Alaskan wilderness. Disaster strikes, as disaster is won't to do when Bruce Wayne happens to be around, and Bruce's life is ultimately saved by a Native American shaman wearing the mask of a giant bat. These events are crucial to a case in Gotham years later, and the way O'Neil links everything further cements his status as one of the greatest writers ever to work on Batman. The first handful of arcs in Legends of the Dark Knight are all excellent, and most have made this list already - but "Shaman" is still the best.
5. The Killing Joke (1988)
Written by Alan Moore, illustrated by Brian Bolland. As mentioned in a previous article, Alan Moore's seminal Joker origin story "The Killing Joke" contains some of the darkest comic book moments imaginable. This is the reason why the Joker is to be feared above all else - whatever tales redefined his murderous character (like "Joker's Five-Way Revenge") or depicted his most basic schemes (like "The Man Who Laughs") take a backseat to "The Killing Joke". The story is split between a flashback-style origin of the Clown Prince of Crime - who was once a young standup comedian, disfigured and forever transformed into the Joker - and an in-continuity game of cat-and-mouse between Joker and Batman. Joker's brutality knows no bounds, and by the end of the book he has captured and tortured Commissioner Gordon, forcing him to watch the ostensible death of his daughter Barbara (the former Batgirl). This was right before "A Death in the Family", which concerned the killing of Jason Todd at the hands of the Joker, and between them the Bat-Family hardly survives thanks to the laughing murderer. "The Killing Joke" is an unsettling, dream-haunting read, but it's a must for any fan of Batman.
4. The Long Halloween (1996-97)
Written by Jeph Loeb, illustrated by Tim Sale. The World's Greatest Detective gets his greatest mystery, the case of the serial killer known only as "Holiday". Jeph Loeb and Tim Sale structure "The Long Halloween" over the course of one year, with each issue featuring a single murder on a single holiday in a single month. The Holiday Killer is responsible for all of them, and everyone in Gotham - Batman, the cops, the gangsters and the supervillains - wants the killer stopped. Christopher Nolan drew heavily upon "The Long Halloween" to bring the Batman/Commissioner Gordon/Harvey Dent relationship to the screen in The Dark Knight. While the murder mystery is the main drive of the story, it is also a backdrop to the souring of that threefold relationship, the transformation of Harvey Dent into the villain Two-Face, and the loneliness felt by all three main characters. Few comic books approach the level of literary tragedy achieved by "The Long Halloween", and while Jeph Loeb has had a long career writing amazing stories for both DC and Marvel, this remains his finest work. And as mentioned in the earlier Loeb entry for "Hush" (#10), the writer's greatest power is in his ability to create something that feels fresh. Most of these characters have been around for decades, but Loeb creates many never-before-seen Gothamites that feel organic alongside the established ones. Really, the established ones feel fresh too - the chief example being The Calendar Man, whose name would suggest the level of excitement his crimes had brought prior to Loeb getting ahold of him. In "The Long Halloween" the Calendar Man - and every other character - feels like a newborn, and as soon as you've read the Dark Knight's greatest mystery you'll want to turn it over and read it again.
