Batman: The Animated Series holds the distinction of being generally regarded as one of the greatest cartoons of all time. Produced and developed by Bruce Timm and the basis for the acclaimed DC Animated Universe, the show celebrated the complexity and darkness of Batman while being sure never to let such dark grittiness eclipse the inherent humor of both cartoons and superheroes. Writing from the legendary Paul Dini and theme music composed by Danny Elfman himself certainly didn't hurt the show's popularity. It turned often-overlooked voiceover performers like Kevin Conroy, Arleen Sorkin, Robert Costanzo, and Bob Hastings into household names.

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It also featured Mark Hamill as the Joker, which is arguably the greatest rendition of the character in all forms of media. However, despite all the talent and technical quality the show boasted, many agree that the true greatness of the show came from its many moments of tear-jerking brilliance. Entire episodes were devoted to heart-breaking conflicts of personal demons, mental health, and acceptance of loss, each doing their level best to dredge as many tears out of viewers as possible. With that in mind, here are the 15 most devastatingly depressing moments from Batman: The Animated Series.

15 "WHY COULDN'T YOU SAVE ME?!" (TWO-FACE, PART 2)

One of the most lauded aspect of BTAS was its approach to the story of classic Batman villain Two-Face. He was introduced early in the show as Harvey Dent, a legitimately good man and friend to Bruce Wayne. Over the course of the first half of the first season, it is slowly revealed that Harvey's charity and kindness hides a dark alter ego that constantly assaults his psyche.

In the dual episodes "Two Face, Parts 1 & 2," an explosion burns half of Harvey's body and the shock of his wounds permanently splits the DA's mind. Though Two-Face's origins are tragic, the most gut-wrenching moment of both episodes is a dream sequence Bruce has in part 2. Desperately trying to stop his friend's transformation, Batman is forced to watch while the disfigured Harvey falls into a glowing red background as he screams his questioning accusation over a building crescendo.

14 THE DUPLICATE'S SACRIFICE (HIS SILICON SOUL)

The episode "His Silicon Soul" focuses on a robotic duplicate of Batman imbued with Bruce Wayne's memories. Believing himself to be the true Batman, the duplicate is confused by his exposed hardware and spends the majority of the episode on a rampage, trying to solve the mystery of his own existence. The scene where he learns the truth is sad enough, but the true heart-breaking moment comes at the end.

After being manipulated by the supercomputer that programmed him and seemingly killing the original Batman, the duplicate realizes that his sole purpose is to end innocent lives. In a moment of self-control and swelling music, the duplicate sacrifices himself to kill his creator and controller, leaving the real Batman to wonder if this mechanized hero had a soul after all.

13 "SO IT WASN'T ALL FOR NOTHING." (BEWARE THE GRAY GHOST)

Made all the more tragic by the recent passing of the late Adam West, "Beware the Gray Ghost" saw West voice the titular character to help Batman. "The Gray Ghost" was a campy television show that helped inspire young Bruce Wayne to become Batman. When a series of crimes mimic the plot of the show, Batman recruits the forgotten actor who played the role to help him solve the case.

The parallels to West and the show that made him famous are numerous and fairly blatant, representing both the glories and pitfalls that came with being shoehorned into an overly-iconic part. The most devastating moment comes when Bruce reveals himself as a collector of Gray Ghost memorabilia and how important the Gray Ghost was to making Batman what he was. West's character reviews both his impact on Batman and pop culture before sighing "so it wasn't all for nothing." RIP.

12 BATMAN BREAKS DOWN (I AM THE NIGHT)

One of the best elements of BTAS was that it wasn't afraid to portray its hero as vulnerable, even weak at times. "I am the Night" is a perfect example. The episode centers around Batman questioning his purpose and wondering if he's having any actual impact of crime in Gotham, despite the assurances of others. His fears are not assuaged when a botched raid puts Commissioner Gordon, Batman's de facto best friend, in the hospital.

Blaming himself for the failed sting, Batman lashes out at his Batcave, tossing computers and chemicals around with the reckless abandon that can only come from existential despair. Seeing Batman, the pinnacle of the cool, collected hero, breaking under the stress of the job is possibly more heartbreaking than loosing him outright.

11 THE FLYING GRAYSONS FALL (ROBIN'S RECKONING, PART 1)

The Emmy-winning two-part episode revealing Robin's origins, "Robin's Reckoning" features a flashback sequence showing the young Dick Grayson and his family of trapeze artists as part of a traveling circus. After the circus owner refuses to pay a protection racket, a gangster sabotages the trapeze lines. During the entirety of the Flying Grayson's performance, the rope visibly begins to fray, building up tension and music.

Finally, the music and viewer's hearts stop for a moment as Dick's parents' silhouettes disappear out of the spotlight and the broken rope swings back into view. The shocked gasps of the crowd as well as the horrified faces of Dick and Bruce are enough to push any viewer over the edge. The rest of the story follows Robin as he tracks his parents' murderer, and his vengeful drive is all the more relatable thanks to this heart-breaking scene.

10 "CRIME HAS NO PUNCHLINE." (THE MAN WHO KILLED BATMAN)

Ironically, one of the most tear-jerking scenes in the entire series came in one of BTAS's most humorous episodes. In "The Man Who Killed Batman," the Gotham underground is tricked into believing that a pathetic goon called Sid the Squid actually managed to kill Batman. While all of Batman's villains have different reactions, the most comedic and real is that of the Joker's. After Batman fails to stop his jewelry store robbery, Joker is forced to accept that his perpetual dancing partner is really gone.

In a rare moment of humanity and vulnerability, Joker passionately rants about his place in the universe and calls off the heist. He then raises his head sadly and lets his terrifying grin drops as he laments "without Batman, crime has no punchline." The legitimate respect Joker seemed to hold for Batman was surprisingly touching and made for a wet-eyed moment.

9 ANNIE'S SACRIFICE (GROWING PAINS)

In one of the more bizarre BTAS stories, Tim Drake encounters a mysterious amnesiac girl who he dubs Annie. Annie can only remember that she's running from her father and the episode is spent with Batman and Robin attempting to shield her from a strangely powerful thug. Turns out not only is her father the shape-shifting Clayface, but Annie herself is actually just a piece of Clayface that separated from the original and gained quasi-sentience.

Tim, who had developed feelings for Annie at this point, is devastated, but viewers were heartbroken when Annie chooses to sacrifice her life to save Robin from her father. Before he can throw Tim off a catwalk, Annie charges into him and reforms into her creator with a sob shared with the audience.

8 BRUCE WAYNE VS. BATMAN (PERCHANCE TO DREAM)

"Perchance to Dream" was one of the most overall tear-jerking moments. Bruce wakes up in a world where his parents are alive and someone else has taken up the mantle of Batman. Finally given the opportunity to relax in a carefree world, Bruce can't help the nagging feeling that there's something wrong. He nitpicks through his perfect world, piecing together each irregularity to solve the mystery.

It all culminates with him fighting Batman in a bell tower, symbolically attacking the image of his psychosis for denying him the perfect world around him. It's not just Bruce trying to figure out how to break the illusion, it's him actively hating the part of him that refuses to let him live there. Bruce wants to stay in his false paradise, but Batman won't let him, and that may be the most tragic aspect of his character.

7 CALENDAR GIRL UNMASKED (MEAN SEASONS)

The crux of the Batman mythos is grounded in mental health. Most of his major villains suffer from mental diseases, his primary jailing site is an asylum, and even Batman himself must suffer from the mental illness of being Batman. However, possibly the most tragic psychotic villain in BTAS was Calendar Girl, a former supermodel who hid her scarred face to take vengeance on an industry that ruined her. She attacks many of her former employers before being stopped by Batman and Batgirl.

When she is arrested, Detective Bullock removes her mask, revealing that her face is actually flawless. Nevertheless, she attempts to hide herself, believing she's hideous. Turns out the pressures of the modelling industry had driven her insane, forcing her to exaggerate any negatives and overlook her beauty. Her sympathetic plight makes for a tear-ripping moment in an already emotional episode.

6 "I DIDN'T COUNT ON BEING HAPPY." (MASK OF THE PHANTASM)

Though not an episode in BTAS, Mask of the Phantasm was a feature-length release of the show. In it, a new villain forces Batman to reflect on his history, particularly his first days as the Caped Crusader and a romance that almost caused him to abandon his mission. One specific scene is as completely gut-wrenching as any in the show. Conflicted about his love, Bruce pleads with his parents' grave in a rainstorm.

He begs the deceased Waynes to forgive him for feeling happy and grovels before their tomb. The truly heart-breaking moment is the realization that Bruce considers being happy a sin, the idea that he could find some enjoyment in life without his parents makes him guilty. It's this exact mindset that forces him to be Batman and will always keep him chained to the cowl, something this moment emphasizes in the most depressing way possible.

5 "I'M SCARED." (EPILOGUE)

Although technically not a Batman: TAS episode, this Justice League Unlimited episode "Epilogue" takes place in the Batman Beyond timeline and has arguably the greatest Batman moment in all of animation. An older Amanda Waller reminisces to full-grown Terry McGinnis and tells him the story of how Batman dealt with Ace, the child telepath and leader of the Royal Flush Gang. Knowing that Ace was dying of a brain aneurysm and her death could have reality-altering effects, Waller gave Batman a device to kill the illusionist.

Instead, Batman listens to the poor, confused child as she describes her abusive upbringing and learns of her encroaching demise. Ace looks up at him and asks "Will you stay with me? I'm scared." Batman complies, remaining with her through her final moments. The image of him holding her hand was enough to make even the most heartless shed a waterfall of tears.

4 "WHY COULDN'T YOU JUST LET ME MAKE BELIEVE?!" (BABY DOLL)

One of the most tragic characters of the DCAU, Mary Dahl is an actress who suffers from a disease that makes her look like a toddler. Driven to madness at her failed career, Dahl resorts to kidnapping the co-stars to her one successful show, a sitcom where she played a toddler as a 20-year old. After freeing her captives, Batman chases her into a hall of mirrors where she takes potshots at him with a doll gun and demands why he couldn't just leave her to her fantasies.

Dahl begins to break down and shoots every mirror where she sees a Batman reflection until she turns to one showing her as a full-grown adult woman. After pausing to shed a few tears, she empties her clip into the mirror, leaving her and the audience crying as Batman gently takes her clicking gun away.

3 THE DEATH OF BATGIRL (OVER THE EDGE)

In one of the opening scenes of "Over the Edge," the fear-based villain Scarecrow throws Batgirl off of a skyscraper. It takes a good ten seconds for her to fall on a police car below. In the car is none other than her father, Commissioner Gordon, and Detective Bullock. The image of Batgirl's broken and battered body is shocking and emotionally destructive enough, but seeing Gordon holding her shattered form as she chokes out "Dad" and watching him pull back her cowl in horror rips the heart in irreparable ways.

The entire following episode features an all out urban war between Gordon and Batman and Batgirl's death is eventually revealed to be a hallucination, but that doesn't make the moment of her passing any less devastating.

2 THE SNOWGLOBE (HEART OF ICE)

"Heart of Ice" was the episode where Dini proved that BTAS was something special. The episode, which won an Emmy for writing, was a poetic tragedy that retold the origins of classic Batman villain Mr. Freeze. Batman investigates a series of ice-based heists and uncovers the sad tale of Victor Fries, who froze his sick wife to keep her alive and is fighting both to keep her in stasis and to attack the corporate executive who put her at risk.

When all is said and done, Fries is put in a special Arkham cell. There, he caresses a snowglobe of his wife and confesses his failure to protect her, hoping that she can hear him "someplace where a warm hand waits." The chilling poetry of the writing and the sheer tragedy of Freeze's plight forces the audience to share a tear with the villain.

1 "HE SAID IT WAS THE CIRCUS." (MAD LOVE)

No list of BTAS moments would be complete without "Mad Love." The story centered on Harley trying to get the Joker's attention by taking out Batman once and for all. While she has Batman tied upside down above a tank of piranhas, he breaks her delusion that Joker actually loves her. Each of the sob stories Joker told Harley to make her fall in love with him are revealed to be lies.

One was about Joker telling an officer that the only time he'd seen his father happy was at an ice show. "Circus," says Harley softly as she stares at the ground, "he said it was the circus." Harley is a victim of abuse and a subtly sympathetic character. Her trying and failing to come to terms with the lies that she's been told and has been telling herself produces the singularly most heart-breaking moment in the show.

Any other Batman: The Animated Series make you sob? Let us know in the comments section!