The all-black appearance of the Judge is a great use of shadow, which feels closer to the original run than the New Adventures episodes, which are typically brighter.
The Batman:The Animated Series episode "Second Chance" previously established that Two-Face could act out in ways he's not consciously aware, when he hired armed men to kidnap him away from his own plastic surgery. The Judge is an expression of the other side of his personality secretly taking control.
I Love the '90s
Councilman Corcoran hands the Judge police files, stored on gigantic floppy discs.
Over the Kiddies’ Heads
Both stories are a frank look at suicidal behavior, without ever using the term. It's very possible that the FOX Network would've allowed a more nuanced discussion of Harvey's mental anguish (while the WB seemed to demand more action per episode), but it's highly unlikely they would've allowed the word "suicide" to be used.
Battle of the Two-Faced Heroes
"Judgment Day" is the final episode of the Batman series, and it's fitting that Alan Burnett, the man responsible for defining so much of the show, co-wrote the script. Burnett was also the main writer behind Mask of the Phantasm, and just as Two-Face is dominated by subconscious desires in the episode, Burnett seems to be using his previous work as a subliminal influence.
An opening scene featuring villains terrorized by the mysterious, shadowy vigilante with a booming voice comes straight from Phantasm, as does the operatic choir that accompanies his appearances. (Michael McCuistion’s epic score for “Judgment Day” is possibly the best of the New Adventures run.) A few minutes into the episode, we're introduced to a corrupt city councilman who resents Batman on some level, an idea that also appeared in Phantasm. Finally, there's the confrontation between Batman and the vigilante, who turns out to be a loved one from Bruce Wayne's past. None of this means "Judgment Day" is a knockoff of Phantasm, the story stands on its own as an examination of Two-Face's fractured psyche, but it's interesting to see where Burnett's head goes whenever he conceives a big, important Batman story.
Although the producers knew this would be their final Batman, the story itself doesn't acknowledge this. (Consciously going out with a nod to the viewer doesn't occur until years later, during the Justice League days.) If the producers were treating the series more as a primetime drama, the story possibly could've benefitted from killing off the villains targeted by the Judge. After all, the audience is supposed to be horrified by the Judge's actions, and the producers probably didn't think they'd need the villains again, anyway. (Hey, maybe they were kept alive specifically for these tie-in comics.) As it stands, we're told the Judge's victims are in critical condition, but most likely, no one was really concerned over the Riddler's fate. The Riddler, by the way, was never the focus of a New Adventures episode, but he always seemed to pop up as cannon fodder or whenever the producers wanted a generic shot of Batman's rogues' gallery.
"Never an Option!" is a direct sequel to “Judgment Day”, postulating on what Harvey would do if he continued on his "good" streak. The heart of this story really comes out during Two-Face and Batman's confrontation in the doomed plane, with Harvey berating Batman for causing his gun to go off -- the thought of firing without asking the coin being pure sin to Harvey. His real anger at Batman, however, comes from Batman's continual interference in his suicide attempts. With Two-Face opening himself up to his true Harvey Dent persona, he's sees no other option for himself. Two-Face must die, but because a direct suicide would be murder, he has to perish while committing one of these good deeds. Templeton's revelation that Harvey knew all along his coin was a fake speaks volumes. It was always an excuse to do some good, before fate or bad luck did what had to be done and ended Harvey's life.
Both stories are equally brutal, and in a sense, thought provoking; not what most would expect from all-ages entertainment, and certainly not a typical plot for the allegedly "lighter" revamp episodes. The two stories play off each other well, and while they adhere to the edict of more action sequences than talky scenes, neither is simplistic children's entertainment.
That's all for now. Thanks to Gravity Falls Poland for this suggestion. If you have choices for cartoon/comics pairings, let me know in the comments or on Twitter. *