Batman has always been one of the most grounded superheroes in mainstream comics, as long as you don’t count his numerous encounters with aliens and teleporting to other planets in the Silver Age. Along with this gritty world of crime in Gotham City that Batman operates in comes more than a handful of heartbreaking moments for the Caped Crusader.
This is the guy whose parents were gunned down in front of him as a child, after all. Batman comics have been noticeably darker and more emotional than other superhero comics, with supporting and main characters dying, having emotional breakdowns, and dealing with various traumas they have accumulated over their violent, crime-riddled, vigilante-filled lives.
10Arkham Asylum: A Serious House On Serious Earth Dives Into The Heartbreaking Origin Of Arkham’s Founder, Amadeus Arkham
Writer Grant Morrison and artist Dave McKean’s groundbreaking Batman graphic novel endures as one of the most ambitious and unique takes on the world of Bruce Wayne and his recurring rogues gallery. It tells the story of Batman diving deeper into Arkham Asylum to quell a riot, while simultaneously uncovering a psychological/supernatural horror that plagues the location and its inhabitants.
The true sadness of the book comes from the heartbreaking origin of Arkham’s founder, Amadeus Arkham, and the murder of his family, as well as McKean’s beautiful, emotionally charged artwork.
9Jason Todd's Brutal Death In "A Death In The Family"
This now-classic Batman story was written by Jim Starlin and drawn by Jim Aparo. This is a painful one, with Batman being unable to save the second person to take on the mantle of Robin, Jason Todd, from the hands of the Joker. Todd is brutally beaten and murdered by the Joker, and Batman sobs over his dead body.
However, maybe the saddest thing about the story is its real-life origins. Editor Dennis O’Neil recognized Jason Todd’s wavering popularity and set up a poll where fans could call in to determine the fate of the second Robin. Obviously, fans voted to watch a child get murdered by a psychopath because they thought he whined too much.
8Batman: The Killing Joke's Deep Dive Into Joker's Origin
Alan Moore and Brian Bolland’s original graphic novel has been critically acclaimed for decades, with good reason. Moore conceives of a now widely accepted “definitive” Joker origin story where he is a failed comedian whose life turned terribly wrong after “one bad day.”
The Joker attempts to prove this is possible to happen to anyone by trying to turn Commissioner Gordon insane. The most unfortunate part of the comic comes early, when Joker shoots Barbara Gordon in the spine, permanently paralyzing her from the waist down.
7Batman Fails To Save People In "The Long Halloween"
Jeph Loeb and Tim Sale’s 13-issue maxi-series is one of the darkest and grim Batman stories to be written. It tells the story of Batman’s early days of crime-fighting and his desperate attempts to stop the elusive killer known as Holiday, who kills their victims on different holidays.
The stories surrounding the individual murders are sad enough, but this comic also features a heartbreaking origin for the disfigurement of Harvey Dent and his transition into Two-Face.
6New 52 Batman: Annual #1 Rewrites Mr. Freeze's Origin
Although a controversial move, Scott Snyder’s retcon for the origin of Mr. Freeze in Batman Annual #1 reinvented the character in an interesting way. Instead of being a scientist who pined over his lost wife, Snyder makes it so that Freeze never actually knew Nora, she was just a woman who was brought into Waynetech to be hopefully cured of her frozen illness.
Freeze grew obsessed with her and Bruce Wayne fired him from the project. Some would argue this decreases sympathy for Freeze, but others say this is even more pathetic and realistic, that sometimes hatred comes from false places.
5Flashpoint: Batman - Knight Of Vengeance (Thomas Wayne Batman)
DC’s Flashpoint Paradox event that eventually launched the New 52 era of comics focused a large part of its run on a pocket universe accidentally created by Barry Allen, where lots of pivotal moments of DC history were altered in significant ways.
One of the most interesting changes was the fact that Bruce Wayne was murdered as a child instead of his parents. This leads his father, Thomas Wayne, to become a violent, murderous version of Batman, and his mother, Martha Wayne, to lose her mind and become the Joker.
4Death Of The Family Is Joker At His Most Gruesome
One of the more climactic and gruesome moments in Scott Snyder’s run on Batman with artist Greg Capullo came in the form of the Bat-Family spanning event “Death of the Family.” This marked the Joker’s big return having previously been absent from the New 52 continuity.
Sure, this comic is sad for having Joker on a murderous rampage, examining the effects this has on the victims' families, but the most horrific moments comes when a brainwashed Alfred seemingly serves the cut-off faces of the Bat-Family. Luckily, this is only a trick.
3Jason Todd Returns In "Under The Hood"
Judd Winick and Doug Mahnke’s story of the return of Jason Todd is as exciting as it is heartbreaking. Spanning the pages of Batman #635-641 and 645-650, “Under the Hood” tells the story of a new, violent vigilante in Gotham City who is seemingly trying to make up for problems he believes Batman is too weak to solve because of his commitment to never kill.
The saddest moment comes when Jason Todd is revealed to be the murderous Red Hood and desperately asks Batman why he never killed the Joker to avenge his murder.
2Gaiman Pens A Tearjerking Sendoff In "Whatever Happened To The Caped Crusader?
Neil Gaiman’s farewell to Batman was initially posited to be the final issue of both Batman and Detective Comics. This didn’t last very long, but it doesn’t stop “Whatever Happened to the Caped Crusader?” from being one of the most tear-jerking stories told in Gotham.
In the comic, Batman’s many villains give stories of how Batman died in various ways. He doesn’t understand what’s going on at first, but eventually, Bruce realizes that he is currently dying and that this is his life flashing before his eyes.
1Superman/Batman Explores The Interior Of The Two Greatest Heroes
Jeph Loeb’s dual narrated title, Superman/Batman gave an opportunity to delve into the interiors of both Bruce Wayne and Clark Kent’s minds. The saddest moment of the initial run of the series comes when Batman has a vision of apparitions of his parents, alive and safe in his arms.
He experiences relief he has never known before, crying and exclaiming that they are safe. Unfortunately, this doesn’t last long as the vision quickly fades, leaving Bruce feeling more alone than ever.