The Riddler reveals his origins when he and Batman are dropped at the harbor.
Tropes for this episode include:
- Alas, Poor Villain: Batman could only feel sorry for Riddler and even expressing disgust against his former lover for turning him into this.
- Backported Development: Batman is shown with his season 4 design in the flashback, which takes place at least prior to season 2, at most before the series.
- Berserk Button: Whatever you do, don't call Edward Nygma "Champ", or use the phrase "Play Ball". Gorman learned first-hand how badly those words set him off. Batman later invokes the later during their fight in the laboratory to set the Riddler off into a blind rage.
- Bitch in Sheep's Clothing: Julie may seem sweet, romantic and understanding, from Riddler's point of view. But in reality, she turns out to be conniving, greedy and cold-hearted.
- Bittersweet Ending: Riddler's been thwarted and there's a possibility Julie will go to prison for criminal negligence (her sabotaging the memory device that fried the professor's brain). But nonetheless, Batman can only pity Riddler, who is not only defeated but severely heart-broken by Julie's betrayal.
- Blatant Lies: Dick has used so many "unbelievable excuses" to get out of class that he admits he'd have only a couple of teeth left if all his toothache tales were real.
- Book Ends: Riddler frames his and Batman's fate to the watery grave as this. Batman intervened the very first time Riddler tried to kill Gorman. And now that they're stuck at the bottom of the ocean with Gorman's stolen chips, Batman is there, at "the very bitter end".
- Cordon Bleugh Chef: One of Dick’s classmates makes a soup using liquorice.
- Everyone Has Standards: Batman refuses to free Julie from her bondage after stopping the Riddler, and coldly tells her a riddle of who is the real villain of the story.
- Face Death with Dignity:
- Initially subverted, when found trapped in their confinement in a sinking container, the Riddler simply poses the riddle "What do I have to lose?" and attacks the Batman. He's quickly subdued.
- After then recounting his Start of Darkness, the Riddler invokes this when he refuses to help Batman escape their underwater containment, saying that A) he doesn't like the Batman enough to help him escape death and B) he's ruined Gorman, his perceived arch-enemy and "... that's as good a note as any to go out on," clearly having given up the will to live. Batman has to appeal to his intellect, posing to him a new riddle that Gorman may not have been the one to ruin his life, to get Nygma motivated to help them both escape.
- Foreshadowing: Once the Riddler finishes his backstory, Batman asking if he's sure it was Gorman tells us that it had to be someone else who sabotaged Nygma's invention.
- Forgotten First Meeting: Not by Eddie, though Bruce did forget, as this episode retconned that "Riddled" was not their first encounter, but in fact, Bruce first met Eddie when Eddie first went after Gorman with that meeting inspiring Eddie to becoming a costumed villain.
- Freudian Excuse: As a bright child, Riddler grew up with a bully-of-a-father who would throw baseballs at the boy's puzzles, making him resent people with no appreciation for mind puzzles (and ball games, for that matter).
- Karmic Death: Julie nearly bites the big one when Riddler tries to weaponize his invention on her, the very same invention she sabotaged and fried someone else's brain with. But it's averted when Batman intervenes.
- Love Makes You Dumb: This is ultimately why Riddler didn't suspect Julie to be real culprit behind the sabotage despite the fact she had technological means to do so as well as the motivation (given that she was initially angry that Edward didn't accept Gorman's deal). He was so blindly in love with her that he wouldn't consider her to be a suspect until his talk with Batman.
- Meaningful Echo: In the flashback, Batman notes that the most obvious answers aren't always the right ones in riddles. Later, when Riddler points out how 'obvious' it was that Gorman sabotaged his invention, Batman remarks more or less what he said in the flashback.
- Moving the Goalposts: It's subtle, but it becomes obvious that the Riddler isn't hoping to match wits with Gorman the way he later is canonically with the Batman and Detective Yinn, he's looking to bully and humiliate a man he believes is his intellectual inferior. This is evident in the opening scene, when Gorman is correctly guessing the answer to his riddle, but the Riddler refuses to hear it because he gagged him. He doesn't want Gorman to prove him wrong. He does the same thing in the flashback when Gorman guesses the ton answer correctly, but then activates the trap anyway after imposing a before unmentioned time limit, clearly trying to stamp out Gorman before he can get any further in his death traps, unwilling to consider the idea that he might lose to someone he considers inferior to him.
- My God, What Have I Done?: Julie's unspoken malicious satisfaction at Riddler's defeat by Batman and Robin is visually cut short by Batman expressing his implicit disgust at her actions to Robin, which alongside Riddler shedding a Single Tear finally makes her appear ashamed of her role in Riddler's Start of Darkness.
- Pulling the Thread: After Riddler finishes explaining his Start of Darkness, Batman voices his suspicion that Gorman might not have been behind the fateful sabotage. Later, when Riddler questions how Batman pieced together that Julie was the saboteur, Batman points out one crucial detail: Gorman, the man Nygma held responsible for sabotaging his invention and ruining him, was a business man, and so wouldn't have the skill needed to perform said sabotage.
- Ship Sinking: So much for Julie and Nygma being a couple.
- Start of Darkness: According to Riddler, Gorman's (alleged) sabotage of Nygma's invention was the tipping point that lead to his life of crime. As he solemnly puts it, it destroyed his "last chance to not be the Riddler."
- Stern Teacher: The cooking class teacher is extremely harsh when critiquing Dick's attempts to cut class and another student's cooking project, although both criticisms have some Jerkass Has a Point moments.
- Sympathy for the Devil: “When is a villain... not the villain?”
- Ungrateful Bastard: Batman saves Gorman's life multiple times, but Gorman calls him a freak the first time and has absolutely no hesitation or guilt about blowing up a ship Batman is on if it means he can kill the Riddler as well.
- Wham Line:Julie: The $64,000 question; why did I sabotage our project? Come on, Edward. It’s not that hard.
