"Batman: The Animated Series" is quite possibly the best interpretation of the Caped Crusader outside of the comic books. There's so much to commend this show: the pitch-perfect voice actors, the stunning animation, the introduction of Harley Quinn, its faithfulness to the source material, and its reinvention of B-list characters are just a few of the series' many great qualities. It's also widely known that the show is, in the eyes of many fans, the definitive version of the Dark Knight and his world.

However, what really sets "Batman: The Animated Series" apart from (if not above) other superhero animated shows is its mature tone. While remaining within the confines of Saturday morning cartoons, the series appealed to kids and adults in equal measure. After all, Batman is a character grown from the tragedy experienced by a young Bruce Wayne. He doesn't just beat up criminals at night while dressed up as a bat. He does whatever he can to give these lost souls a second chance at life. With the amount of pathos built into the premise, there are plenty of somber moments throughout the show, the 12 saddest of which we're looking at here.

Mr. Freeze Apologizes To His Wife — Heart Of Ice

Mr. Freeze is stealing equipment from GothCorp offices around Gotham City with a gun that can freeze anything. Batman deduces that he's constructing an even more powerful weapon and determines where he'll strike next. However, Batman is overpowered in his first fight with this frosty foe. Bruce Wayne meets Ferris Boyle, the CEO of GothCorp, who tells him that the only person with a grudge against his company is a former scientist named Victor Fries, whose research was shut down because of costs. Previously thought dead, he's returned as Mr. Freeze, and he has a score to settle with Boyle.

This may seem like a predictable revenge tale on its surface, but Mr. Freeze has a deeper reason for his animosity. He's out to avenge the death of his wife at the hands of the ruthless Boyle. Mr. Freeze is stopped by Batman and sent to Arkham Asylum before he can carry out his final act of vengeance, resulting in the standout moment when he apologizes to his wife, Nora, for not saving her, the sole purpose of the research that Boyle ended. This moment is made more tragic when Mr. Freeze cries, as he previously states that he has no more tears to shed. Considering Boyle's cruel treatment of Fries and his wife, we can't help but wonder who the real cold-blooded one is.

Joker Questions His Purpose — The Man Who Killed Batman

"The Man Who Killed Batman" opens with a typically dark and stormy night in Gotham City as the nebbish Sidney Debris arrives at the home of crime lord Rupert Thorne. Thorne's honored to host Sidney. After all, he's the man who killed Batman. However, Sidney's bothered by the notoriety, as it's attracted unwanted attention from the criminal underworld. He then relates a story about how the Joker, Batman's archnemesis, was unconvinced that this nerdy little man finished off the Dark Knight, something the Clown Prince of Crime has dedicated his life to. To prove that Batman really is dead, the Joker sets up a jewelry store heist, knowing that his foe can't resist the urge to carry out justice. If he's alive, that is.

During the heist scene, we see the Joker's excitement gradually change from excitement over meeting Batman again to annoyance with his tardiness to, finally, sadness at the realization that his primary foe may actually be dead. It's odd to feel bad for a criminal, especially one as vile as the Joker, but knowing that he's so maniacal so much of the time, we can't help but sympathize with his quiet acceptance that his life's purpose has been stripped from him. The Joker's so sad that he even tells Harley Quinn (who's decorated herself with stolen loot) to put the jewelry back. That's how sad the Joker is!

Bruce Wayne's Fantasy — Perchance To Dream

Batman is knocked out during a mission pursuing some criminals one night and wakes up the next morning as Bruce Wayne — and only Bruce Wayne. In this new world that Wayne has awakened in, he's not Batman; He's just a wealthy playboy. Even more shocking to him is the discovery that his parents are still alive. Bruce can't believe it and spends the rest of the day trying to figure out what's really going on. After meeting with Dr. Leslie Thompkins, he's convinced that his confusion is simply his frustration at achieving so little in his life. With his suspicions assuaged, Bruce accepts this version of his life.

Of course, this is all a dream world concocted by the Mad Hatter. However, that doesn't detract from the emotional heft conveyed by Bruce getting a chance to live a normal life with his parents still living. It enhances it. There are clues throughout the episode that hint that Wayne's new reality isn't real. The saddest part is when, after his reassuring discussion with Thompkins, Bruce embraces his father and invites him and his mother to dinner with Selina Kyle. Bruce even calls his father "sir," a reference to the intense respect he had for him as a child. Seeing Wayne so happy is a rare occurrence, and it's made even more tragic knowing that it will soon be stripped from him again.

Dick Grayson And Bruce Wayne's Friendship Dissolves — Old Wounds

During a routine mission to take down some thugs, Tim Drake (who's taken over as Robin from Dick Grayson) is rescued by Grayson's alter ego of Nightwing. Drake gets annoyed with Grayson's surly attitude and compares him to Batman. Grayson is about to leave until Drake presses him on why he ended his partnership with the Dark Knight. Years earlier, when Grayson was Robin, Batman took Barbara Gordon on a mission, knowing her identity as Batgirl. Nightwing arrives to help but is shocked to discover not only that his girlfriend kept her superhero identity hidden from him (they were dating at the time) but that Batman knew about it, too.

In pretty much all media, Batman and Robin have a tumultuous friendship. However, this is one of the most dramatic portrayals of their turbulent association. When Grayson learns that his mentor kept such important information from him, he punches him in the face. Knowing that it's useless to talk sense into him, Batman lets Grayson go on his own as a dismayed Batgirl watches. Grayson is right to feel deceived by Batman, but Batman is right not to share someone else's secret. Because so much of their relationship is built on mysteries, this blowup was bound to happen. While the two would eventually patch things up, it's never easy seeing the Dark Knight and the original Boy Wonder fight.

The Gray Ghost Contends With His Irrelevance — Beware The Gray Ghost

"The Gray Ghost" is a black-and-white TV show about the crime-fighting exploits of its titular character and had a lasting influence on Bruce Wayne, who watched it as a child. Unfortunately, the actor who played the Gray Ghost, Simon Trent, has fallen on hard times since his show was canceled. Unable to find new work, he sells memorabilia to a toy collector just to stay afloat financially. However, he soon lands a gig fighting crime — for real. Batman is on the trail of a bomber wreaking havoc in Gotham City and believes he may be connected to the old TV show. He needs Trent's help.

While this episode has an uplifting ending, we're put through the emotional wringer to get there. The most heartbreaking scene takes place when, after learning that he lost the role in an upcoming project, Trent trashes his meager apartment in a fit of rage. Alone in the realization that he's all washed up and forgotten, a despondent Trent sits in the mess. It's a devastating scene, as Trent must accept that his past success has led to his present failure. In a brilliant casting decision, original "Batman" actor Adam West voices Trent, bringing with him the swashbuckling charm that typified his portrayal of the Dark Knight in the 1960s TV show while imbuing the character with a melancholy that only an aging actor can understand.

Harley Quinn's Revelation — Harley's Holiday

Harley Quinn is finally rehabilitated after her most recent stint in Arkham Asylum. Eager to start a new life, she treats herself to a new outfit, but a misunderstanding causes her to panic. She steals Bruce Wayne's car — with his friend Veronica Vreeland in it. While Harley knows she's done nothing wrong and plans to let Vreeland go free, she must skip town because the authorities are after her, and she doesn't want to ruin her last chance at going straight. Things get complicated when she returns to her old criminal buddy Boxy Bennett, who the police are also after.

Harley's done some pretty terrible things as a fugitive, but she was largely acting under the Joker's influence, making her one of Batman's more tragic villains. We genuinely root for her when she tries to live an honest life and feel bad when a mix-up results in her falling back into a life of crime. The real kicker is when Batman confronts her and tries to convince her to step back from the edge, assuring her that she can still retain her freedom. Harley, however, has been pushed far enough and lashes out at Batman, screaming about not being good enough for the world. The sad part is that she's right. Regardless of her honest attempt to become a law-abiding citizen, her felonious life will always catch up to her. That still doesn't stop Batman from fighting for her redemption, though.

Batman Loses His Cool — I Am The Night

After the recently accused Penguin is let off the hook, Batman questions his efforts to clean up Gotham City. He then visits Crime Alley with Dr. Leslie Thompkins to place roses on the spot where his parents died, as it's the anniversary of their murder. Their vigil is interrupted by some crooks chasing a small boy named Wizard. Batman breaks up the scuffle, but it makes him late for a police raid. Commissioner Gordon is critically injured in the ensuing shootout, which Batman feels responsible for. Arriving at the Batcave, Batman destroys much of his equipment in a rare lapse of composure.

We rarely see Batman lose his cool, but when it happens, it's a doozy. Alfred, worried about Batman, sends his old friend Dick Grayson to check in on him. Upon entering the Batcave, however, he encounters a dejected Batman who rants about how useless it is trying to keep Gotham safe, how he's more of a tourist attraction than a hero, and how he thinks it's time to quit being the Caped Crusader. While he ultimately comes to his senses and saves the day, it's still shocking to see the usually stoic Batman crack under the pressures of his crime-fighting life. It's hard to imagine Bruce Wayne without Batman, but even he sometimes goes through rough patches. As brilliant as he is, he must also accept that he can't save everyone.

The Deaths Of Dick Grayson's Parents — Robin's Reckoning, Part I

Batman and Robin catch a group of criminals, and they interrogate one for info about who they work for. When the thug mentions the name "Billy Marin," Robin demands more details. However, Batman tells Robin to drop it and sends him to the Batcave. As expected, Robin's bothered by Batman's unusual secrecy. He researches the name himself and is stunned to learn that it's a false name for Tony Zucco, the man responsible for the deaths of his parents years earlier. Robin's understandably angry at Batman for thwarting his efforts to avenge his parents and sets out after Zucco himself.

We're shown a flashback of the murder of Robin's parents, which sees Zucco sabotage their circus act, resulting in their falling to their tragic deaths — all before young Dick Grayson's eyes. He's soon adopted by Bruce, who understands the pain of helplessly watching one's family die and the eternal scars it leaves. We've all seen Bruce Wayne's parents murdered countless times, but it still doesn't lessen the impact of seeing Grayson's parents getting murdered. We can only take solace in the fact that, like Bruce, he eventually channels the trauma of this brutal experience into something positive.

Dr. Leslie Thompkins Consoles Batman — Appointment In Crime Alley

Corrupt businessman Roland Dagget hires an arsonist named Nitro to blow up Park Row (aka Crime Alley) in a way that looks like an accident as part of a broader plan to take over the area. However, Crime Alley is where Batman's parents were murdered, and he's on his way there to pay his respects — along with Dr. Leslie Thompson. While some buildings are unfortunately destroyed, most of Crime Alley is unharmed, and Batman brings the culprits behind the destruction to justice. However, Dagget convinces the authorities that he had nothing to do with the bombings and is let off the hook, much to Batman's dismay.

The final scene is the most heart-wrenching, as it sees Batman, lamenting Dagget's escape from justice, lay two roses on the spot where his parents were gunned down. Thompkins reassures him that Dagget will pay for his crimes eventually, but for now, this is one fight the Dark Knight can't win. Batman rarely lets his inner anguish show, and it's even rarer for him to display those emotions in front of someone else. This scene is a testament to how much Batman trusts Thompkins; He's willing to share his grief with her. It's a touching reminder that Batman has a heart beneath his stony exterior.

Robotic Batman Copy Destroys Itself — His Silicon Soul

A criminal cadre attempts to steal some expensive equipment from a high-tech warehouse, where they encounter a robotic clone of Batman (called a "duplicant"), which easily dispenses with them. The robotic Batman bests the Caped Crusader in combat and reverts to its previous mission: destroy all of humanity and take over the world with other duplicants. But before it can carry out its directive, the real Batman arrives and deduces that the robot has emulated his personality so well that it refuses to kill. Batman's theory turns out to be true when the duplicant seemingly kills Batman and destroys itself.

Batman and Alfred then muse on the morality of the duplicant and conclude that, despite its electronic innards, it did indeed have a soul of sorts. A robot Batman running amok seems like a silly premise, even in a kids' show, but "His Silicon Soul" treats the idea of artificial intelligence with, well, intelligence, exploring the question of how ethics can be programmed into something completely synthetic. The Batman duplicant's dilemma is pretty convincing as it vacillates between binary code-induced instructions and free will, culminating in one final act of shame and compassion. This episode is quite deep for a cartoon.

Batman Comforts Mary Dahl — Baby-Doll

Several actors from an old show called "Baby-Doll" have gone missing, and Batman and Robin discover they're connected to the show's star, Mary Louise Dahl. Dahl has a condition wherein her physical appearance will remain that of a five-year-old. She became jealous when another actor joined the show and stole her spotlight and grew resentful when her career after the show failed. She arranges a "birthday party" in her honor, with all of her kidnapped co-stars in attendance, that will end with all of their deaths, including hers. Batman and Robin rescue the actors, but Dahl escapes into a hall of mirrors. She sees herself in a mirror that makes her look taller and immediately starts crying.

Even though Dahl tried to commit mass murder, Batman takes this moment to comfort the grieving former actress. Obsession is something Batman's quite familiar with. He knows that the trauma of the past can haunt someone for the rest of their life and drive them to commit extreme acts. As villainous as Dahl is, her actions are understandable, if not commendable. She was so used to the attention that she lashed out when it went to someone else and became bitter when her medical condition prevented her from cultivating the career she always wanted. Dahl never got the chance to rebuild herself, so she deserves that brief moment of comfort from someone who understands.

Harvey Dent Returns To Arkham Asylum — Second Chance

Two-Face is about to undergo a medical procedure to remove the scars that cover half his face and hopefully restore his original persona of Harvey Dent. Just before the operation, he's captured by a group of henchmen and taken to an unknown "boss." After some dead ends, Batman traces Dent to an abandoned building and finds out that Two-Face himself arranged his own kidnapping. Batman deceives Two-Face with a trick coin, forcing him to make a choice on his own and be taken back to Arkham Asylum — but not before Bruce Wayne assures him that he'll always be there for him.

Part of what makes Batman's rogues' gallery so good is that many of them aren't just people committing crimes for their own sake; They're tragic figures who took the wrong path after being dealt a bad hand. Harvey Dent/Two-Face is one of these figures. Bruce knows this, and even after all of the terrible things his old friend has done, he still sees the potential good inside him and hopes for his redemption. This final moment is more tragic because Two-Face is in his "Dent" persona, implying that no matter how hard he tries to revert to his original self, he will always be haunted by his sinister other half.

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