Batman: The Animated Series, alongside its continuations The Adventures of Batman and Robin and The New Batman Adventures, is one of the most beloved animated shows of all time, and a firm favorite with both younger and grown-up fans. To many, it is the definitive version of Batman and Gotham City, and of many of the Caped Crusader's iconic villains.
One of the reasons it was so popular with fans was that, despite being a children's TV show, it did not shy away from strong emotions. Episodes could be funny, but they could also be heartwarming, or scary. A great many of them also contained moments that were poignant, melancholic, or downright tragic.
10 Dick Grayson Leaves Bruce & Barbara in "Old Wounds"
Dick Grayson, across his various incarnations, is beloved by fans as the first Robin, whose relationship with Bruce caused him to strike out on his own as Nightwing. Viewers see in the episode "Old Wounds" how their relationship deteriorated in this continuity. Following several disagreements in their methods and philosophies, Dick storms away from Bruce to see Barbara Gordon, his girlfriend.
With the Joker hatching a new plot, however, Dick is nowhere to be found when Batman needs him, causing Bruce to instead recruit Barbara, who he knows is Batgirl. Once he catches up and saves Barbara, Dick is unable to trust that Batman didn't manipulate the situation and is unable to trust Barbara after learning about her secret identity. One punch later, he leaves the two, and doesn't return for years.
9 Duplicant Batman's Attempts To Talk To Alfred
The robotic copy of Batman, made by the rogue supercomputer H.A.R.D.A.C., is ultimately a villainous character who seeks to replace humanity with Duplicants like itself. However, it also believes itself to be the real Bruce Wayne, to the extent of sacrificing itself when it believes it has broken Batman's famous 'no-kill rule.'
Before it learns that it is not Bruce Wayne, the Duplicant attempts to talk to Alfred, Bruce's oldest friend. Seeing the Duplicant, however, Alfred first attacks it, and then retreats. The Duplicant tries to talk Alfred down, pleading, but is unable to, and is left deeply hurt believing the man who raised him is afraid of him.
8 A Simple Misunderstanding Leads Harley Quinn Back Into Arkham
Fan-favourite DC character Harley Quinn debuted in Batman: The Animated Series as one of the Joker's henchmen, who nonetheless gained a few episodes with herself as one of the focal characters. In "Harley's Holiday," she is free of the Joker's influence and is declared cured and safe enough to leave Arkham, promising Bruce Wayne that she'll go straight.
When she accidentally sets off the security alarm in a shop, however, and guards try to help, Harley's instincts lead her to believe that they think she's stolen it. Her initial reaction leads her to steal a car to escape, and what follows is a chase and a kidnapping that sees Harley returned to Arkham when freedom had been so close.
7 Harvey Dent's Cure Being Sabotaged By Two-Face
It is no surprise to viewers that many of the saddest moments in Batman: The Animated Series involve villains, as Batman's rogues gallery is full of tragic characters who truly do belong in a mental institution, not a prison. In "Second Chance," Harvey Dent has been improving through therapy, and is en-route to have a procedure done that may remove his Two-Face persona altogether.
However, the surgery is interrupted, and Dent is kidnapped. When Batman and Robin track the kidnappers down, they find a trap by Two-Face. Batman sets a trap of his own, replacing Dent's coin with a fake one to force him to make his own decisions, and Dent finds himself split between his two personas. After his life is saved, he is back to Arkham Asylum, with his chances of a cure dashed.
6 Victor Freeze Apologizes To His Wife
Fans often consider Mr. Freeze to be one of the most tragic Batman villains, as a man suffering from a chronic condition, often fighting to avenge or cure his wife. This is no different in Batman: The Animated Series, when the episode "Heart of Ice" sees Freeze rampaging against his former boss, Ferris Doyle, whom he believes has killed his wife.
Once Freeze is stopped and placed in Arkham Asylum, he speaks to a model in a snowglobe in his cell as if it were his wife, apologizing in shame for not being able to do anything. Watching from nearby, even Batman is moved.
5 The Death of Dick's Parents
Dick Grayson came into the care of Bruce Wayne because, much like Wayne himself, he was orphaned at a young age. When Haley's Circus came to Gotham, a local gangster attempted to extort them. When they refused to pay, he sabotaged the high-wire act, known as the Flying Graysons.
After his portion of the routine was done, Dick looked at the trapeze and saw the ropes fraying. With no net, he called out to his father, but was unable to warn his parents before they both put their weight on the rope. The viewer doesn't see them fall, but Dick does.
4 Annie Dies Not Sure If She Was a Real Person
In The New Batman Adventures, episode "Growing Pains," Robin encounters a girl named Annie, who doesn't know much except that she is running from somebody. Over the course of the episode, it is revealed that Annie is merely a part of Clayface, and he's trying to get her back to reform himself.
Annie breaks down upon hearing this, while Robin tries to persuade her that she is a real person. When Clayface does absorb her, however, she ceases to exist, leaving Robin grieving for her alone.
3 Freeze Refuses To Save Nora
While saving his wife is the whole of Freeze's ambitions, he once had the chance to do so, and turned it down. Freeze is kidnapped by Grant Walker, a billionaire who arranges to have Nora Fries cured if Freeze repeats the process that made him what he is on him.
It becomes clear, however, that Walker plans to freeze not just himself, but the entire world. Freeze goes along with Walker until Batman points out that Nora would be waking up to a dead world, not the one she loved. Out of love for his wife and refusal to do that to her, Freeze turns against Walker and stops him from destroying the world, but at the cost of her cure.
2 Babydoll's Moment Of Reflection
Mary Dahl is another tragic addition to Batman's rogues gallery, a former actress afflicted with a condition that leaves her looking like a child, despite being thirty. Unable to get work or even form a single proper adult relationship due to her appearance, Mary snaps, becoming the murderous Baby Doll.
Batman engages in a chase with her that leads to a Hall of Mirrors, where one of them reflects Babydoll as she longs to be—a normal 30-year old woman. After failing to kill Batman, Dahl instead smashes the mirror, firing until her gun clicks empty, sobbing all the while.
1 The Joker's Worst Abuse Of Harley Quinn
Various times throughout Batman: The Animated Series and other media featuring Harley Quinn, the audience gets to see a textbook abusive relationship between her and the Joker. While individual counts of abuse stand out, one from The New Adventures of Batman, episode "Mad Love," is considered by many fans to be the most shocking.
After Harley makes the 'mistake' of capturing Batman, and then explaining to the Joker why the deathtrap she has him in is funny, the Joker lashes out at her physically, claiming that a joke you have to explain isn't a joke at all. This assault culminates in Joker pushing Harley out of a window. Even when in near death from her injuries, all she does is whisper that it is her fault, for not getting the joke.