Since his introduction by Bob Kane and Bill Finger in 1939's Detective Comics #27, the world famous Batman has attained the biggest footprint in modern comics. In those almost ninety years of print, he has amassed some of the best-written and most enjoyable stories in comics.

Batman's comics often show him at his best but, since starting his career, he's seen some incredibly low moments too. Every superhero has their share of defeats and tragedies, but the Caped Crusader's gritty tone has made him a prime target for some of the darkest stories ever. While not every one of these rock-bottom crashes is necessarily marred by tragedy -- and some are more a case of wounded pride -- others include events in Batman's life that are so dark, they've even shocked the villains.

10 Batman Gets Knocked Down By Hal Jordan

Green Lantern Rebirth #6 (Geoff Johns & Ethan Van Sciver)

In the 1990s, Hal Jordan turned to villainy when his home of Coast City was destroyed by Mongul and Cyborg Superman. Following this, he became Parallax, who saved the Earth in the final moments of The Final Night. Despite trying to redeem himself in this story, Batman made clear that he wasn't buying it, pitting him against the more forgiving Superman. Years later, Hal was finally redeemed in Green Lantern: Rebirth (Geoff Johns & Ethan Van Sciver), revealing the parasitic villain Parallax to be responsible.

While a great story for Hal Jordan, Green Lantern Rebirth also concludes with a humiliation for Batman as, reversing a famous Justice League International moment, Jordan knocks him down with a single punch. The moment humbled the Caped Crusader in front of Justice Leaguers and Corps members alike, later told to back off by Alan Scott when he tried involving himself in the defeat of Parallax.

9 Bruce Gets Jokerized By The Batman Who Laughs

The Batman Who Laughs #1-7 (Scott Snyder, Jock)

In the aftermath of Barbatos and the Nightmare Batmen waging war on the DCU, Batman is charged with finding and catching his horrific counterpart. After Batman Who Laughs and his partner, the Grim Knight, assault Blackgate Prison in search of Joker, the Clown Prince of Crime decides that the only way Bruce can get the advantage is to become unpredictable -- so he infects him with his toxin.

For much of The Batman Who Laughs, Bruce is slowly becoming more unstable as Joker's toxin begins to take effect, causing mood swings and violent outbursts, signalling his transformation into the villain. In fact, by the final issue, readers are almost left to wonder whether Prime Earth Batman is any match for the toxin.

8 Frank Miller's Batman Abuses Robin

All-Star Batman and Robin, the Boy Wonder #2 (Frank Miller, Jim Lee)

In 2005, DC Comics released the All-Star line, a series of comics with superstar creative teams meant to serve as the definitive take on key heroes. While Grant Morrison and Frank Quitely succeeded in this mission with flying colors, the team-up of Frank Miller and Jim Lee had the opposite effect. In a series full of the gritty excesses of the '90s and Miller's signature writing style, what should have been a dream team ended with some of Batman's worst moments.

While the series has been remembered for many things, it's ultimately Bruce's treatment of Robin that stands out as the worst part of his characterization in the series. In this series, Bruce's cold, abusive attitude towards his wards as mere soldiers in his war was cemented -- and it has been terrible for the hero's reputation. Ultimately, however, it was the quality of the series itself that left a stain on the character's history (as well as arguably his most significant writer since the Modern Age began).

7 Batman's Back is Broken By Bane

Batman #497 (Doug Moench, Jim Aparo, Dick Giordano, Adrienne Roy)

Created by Chuck Dixon and Graham Nolan in Vengeance of Bane, the titular villain is introduced as a driven anti-Batman, sharing the hero's intelligence, cunning and strength but with none of his privileges. After breaking out of his prison home, he sets off for Gotham with his fellow inmates, on a quest to take Gotham from Bruce -- and break the Bat in the process.

During the "Knightfall" story, Bane orchestrates a breakout from Arkham Asylum, forcing an increasingly exhausted Batman to round up his entire rogues gallery in a few nights. At the end, he is so exhausted that Bane -- who deduced Bruce's identity -- is able to break into Wayne Manor and break his enemy's back in the Batcave. To make matters worse, a demoralized Wayne names Azrael his successor, which almost destroys the Caped Crusader's reputation in the city.

6 Catwoman Calls Off The Wedding

Batman #50 (Tom King, Mikel Janin)

During Tom King's run on Batman during Rebirth, he laid the groundwork for The Dark Knight's romance with Catwoman finally coming full circle. In what has been regarded as one of the biggest bait and switches in comics, the story counted down to the long-awaited wedding between the two characters in the fiftieth issue. However, at the last minute, the Cat broke things off.

The dissolution of the Bat and Cat engagement was revealed to be even worse than had been let on. It was shown that it was actually at the behest of Bane and Flashpoint Batman, who worked together for their own agendas, with Thomas wanting to break his son's spirit to dissuade him from being Batman.

5 Batman Becomes Addicted To Venom

Legends of the Dark Knight #16-20 (Dennis O'Neil, Trevor von Eeden, Russell Braun, José Luis García-López, Steve Oliff)

Legends of The Dark Knight was an ongoing series that followed Batman in out-of-continuity adventures (though some of these stories have been rolled into continuity). The fourth story in the series deals with Bruce Wayne becoming addicted to Venom, the serum that gives Bane his enhanced strength. However, he also suffered side effects.

As Batman's dependence on Venom grew, his mind deteriorated, throwing him into mood swings and fits of rage, threatening criminals that he'd rip their heads off. After his addiction caused him to be abusive towards everyone around him, Bruce took advantage of a moment of clarity, tossing the drugs and asking Alfred to lock him in the Batcave for rehab. After a month, he emerged stronger, making this story both one of the darkest but also resilient chapters in his career.

4 Batman Takes Down The Justice League in "Tower of Babel"

JLA #43-46 (Mark Waid, Howard Porter)

"Tower of Babel" follows Ra's al Ghul's war on the Justice League, using Batman's secret contingency plans against his friends to immobilize them. His fight against the League was both physical and psychological, with Bruce getting a nasty shock when the villains dug up the graves of his parents and stole their bodies.

"Tower of Babel" stands out as a key story in both Justice League and Batman history, as the story that cemented the mistrust between The Dark Knight and his teammates. After talking things over, he lost his spot on the League and, although he didn't regret having the secret plans, left the team in disgrace. History would repeat itself when Ra's al Ghul later took control of the Brother Eye satellite program from the hero, using it to cause a second crisis against the League.

3 Batman Gets Brainwashed By Deacon Blackfire

Batman: The Cult #1-4 (Bernie Wrightson, Jim Starlin)

Batman: the Cult is widely regarded as one of the finest -- and darkest -- stories in DC history, thanks to its psychologically-driven plot by Jim Starlin and fantastic art by Bernie Wrightson. The series follows the Caped Crusader's investigation into a violent cult in Gotham, led by the charismatic Deacon Blackfire, who wishes to murder the city's homeless population. When Batman finds them, he's captured and brainwashed into the cult.

The fact that Batman lost control of his mind wasn't the worst of things. Under Blackfire's influence, he aided the cult in their murders, forcing him to cross the one line he'd never violate. While he does eventually regain his senses, the hero is haunted by the actions he took, and is eventually able to defeat Blackfire -- but in the process he turns the cult against him. It's made clear throughout the story that the hero is traumatized by his time in the cult.

2 Batman's Greatest Failure, The Death of Jason Todd

Batman #426-429 (Jim Starlin, Jim Aparo, Mike DeCarlo, Adrienne Roy)

Following Dick Grayson's joining of the Teen Titans, Batman found a new Robin in Jason Todd. After taking him under his wing, however, he failed to prove a popular replacement in the eyes of readers and, in the lead-up to "Death in the Family," (Jim Starlin, Jim Aparo & Mike Mignola) they famously voted to have him killed. The story follows the capture of Todd at the hands of Joker, who proceeds to beat him with a crowbar, leaving him for dead in an explosion.

The death of Jason Todd threw Batman into one of the darkest chapters in his career, with the hero even contemplating killing the Joker once and for all. The story concludes with the revelation that Joker has become a diplomat for Iran, hoping to use his diplomatic immunity as a shield -- only to attack the United Nations. In the fiery conclusion, Bruce fights his enemy in a helicopter, leaving him for dead when it crashes and burns.

1 Bruce's Dark Future as 'The Last Knight on Earth'

The Last Knight On Earth #3 (Scott Snyder, Greg Capullo)

The Last Knight On Earth serves as a Black Label conclusion to a Detective Comics story by Scott Snyder and Greg Capullo, which revealed Bruce's use of cloning to continue his legacy. In the miniseries, a young clone of the Caped Crusader wakes up in an underground bunker, only to discover that the world above has ended. With a dismembered Joker head in a Lantern, he sets off on a journey to discover what happened.

The Last Knight On Earth concludes with the horrifying discovery that the original Bruce Wayne has become the tyrannical villain Omega. However, it doesn't end there. The reason he turned bad was revealed to have been caused by brutal trauma suffered at the hands of a mob of people, who he himself tried to save by bringing them into the Hall of Justice. Wayne recounts how he was literally torn apart at the hands of the savage crowd, making his fate one of the most brutal in DC history.