Written by Grant Morrison, illustrated by Klaus Janson. Gotham mafia dons are being murdered one by one, and the remaining few have no choice but to turn to their enemy Batman for help. They propose a suspension of all organized crime in the city while Batman hunts the mysterious killer, Mr. Whisper, and Batman begrudgingly agrees. Equal parts M., Faust, and whatever else was rattling around in Morrison's fevered brain at the time, "Gothic" cracks the Top 30 by adding new twists and ancient motivations to the legend of the Dark Knight. Mr. Whisper makes for a hell of a villain in Morrison's hands, too, and no matter how many obscure villains the cantankerous writer cares to resurrect for their day in the modern sun, Whisper is the most effectively terrifying of the bunch.
29. The Secret Of The Waiting Graves (1970)
Written by Dennis O'Neil, illustrated by Neal Adams. The indomitable pairing of writer Dennis O'Neil and artist Neal Adams make this list more than once, first with their 1970 issue "The Secret of the Waiting Graves". Bruce Wayne, on a business trip to Mexico, stumbles upon some strange going-ons in the family graveyard of the associate's estate. This story is a great bridge between the Silver Age and some more modern-seeming comics stories, retaining elements of the former while still holding up to readings several decades after publication. A few plot elements are a bit contrived (like Bruce being in Mexico at all), but "The Secret of the Waiting Graves" is full of action and suspense, and features some incredible art from the legendary Neal Adams.
28. Black And White (1996)
Written and illustrated by various. The history of the Dark Knight in the comic medium is a dark one, and rarely since the Golden Age have we had much opportunity to laugh our heads off while reading Batman. Black and White changes that in fresh ways, providing a series of vignettes, each by a different writer and artist, featuring Bruce Wayne and Co. in a collection of fables ranging from the darkly dramatic to the hilariously zany. The highlight is A Black and White World by Neil Gaiman and Simon Bisley, featuring Batman and the Joker backstage in between scenes from the comic books.
27. Son Of The Demon (1987)
Written by Mike W. Barr, illustrated by Jerry Bingham. Popularized and possibly canonized by Grant Morrison's 2006 rehashing in "Batman & Son", Mike W. Barr's Elseworlds-style tale (or maybe it's officially Elseworlds, I can never tell) "Son of the Demon" tells of a relationship between Bruce and Talia al Ghul, daughter of Batman nemesis Ra's al Ghul. His differences with Ra's obviously come into conflict whilst romancing Talia, and the news that Talia is pregnant only serves to further complicate things. Ra's himself is in fine form here, but the relationship between Bruce and Talia is where the real magic lies. Grant Morrison's Damian Wayne was a divisive character, but it's likely he owes everything to "Son of the Demon".
26. The Cult (1988)
Written by Jim Starlin, illustrated by Bernie Wrightson. Writer Jim Starlin is at his most insane in The Cult, which pits Batman against a group of religious fanatics led by the charismatic Deacon Blackfire. Batman is subsequently captured and brainwashed by the cult, leading to violent hallucinations and extreme actions that Bruce Wayne would certainly regret. This isnt Starlins tightest writing, and parts of the book do feel derivative of Frank Miller but The Cult stands on its own two feet well enough, and is likely to be one of the darkest Batman tales youll ever read.