I'm deeply unwell about 'Nygma frees Penguin's Mind' from the Gotham OST. Especially after noticing that it plays in exactly three scenes across Seasons 2 and 3. In each of these three scenes, Oswald Cobblepot's craving to be loved is being pitted against his craving to be untouchable. (Nobody in the world, by definition, can have both). 1) The namesake of the soundtrack. 02x09, 'A Bitter Pill to Swallow.'
Ed Nygma 'frees Penguin's mind' by telling him that the murder of Oswald's mother has eliminated his biggest weakness. Oswald reacts with fury, and holds a knife to Ed's neck, screaming that his mother was the only one who ever cared about him. By this point in the story, Ed knows him well enough to know the exact words to move him: if Oswald loves nobody, then he is "a man who cannot be bargained, a man who cannot be betrayed, a man who answers to no one but himself." Oswald never wants to be the powerless person he was in Season 1 again. Dependent on the goodwill of superiors in a world where betrayal is more certain than death. His disability (the result of his former boss smashing his legs) makes him more vulnerable still. Even Ed is unthreatened as Oswald's shaking hand presses a blade to his throat. Consciously embodying the phlegmatic detachment he invites Oswald to pursue. To set the Penguin free. Prior to this, Oswald had been telling himself that everything he did to fight his way to the top in Gotham's terrible criminal underworld, he did for his mother. But if that were true, why does he mask the very Hungarian heritage she cherishes, going by Cobblepot when she knows she is Kapelput? 2) 03x02, 'Burn the Witch.'
Once again, the Penguin is in a position to kill someone who sees right through him and says so, causing him to not only relent but to readjust his self-perception. It has been rightfully said by fans that if Gertrud Kapelput was Oswald Cobblepot's mother, then Fish Mooney was the mother of the Penguin. Fish even takes credit for it. She tells him "you're mine", that he's "the terror of Gotham", that she sees him as the culmination of unwitting if brilliant decisions on her part as a mentor; the Penguin is their shared masterpiece. That name truly would not exist without her, because she was the one who gave him the disability that inspired it. She becomes emotional as she tells him how proud she felt to "bring [him] into being", and almost sheds tears when he wavers and looks down at the feet she maimed. None of this is fear for her life. She could have used her compulsion superpower to escape at any time. Oswald chooses to lower his gun. Because Fish gave him something he always wanted but could never have from his mother: love paired with the knowledge of who he was. He kept Gertrud in the dark. When she tearfully asked him if he ever harmed anyone, pleading that further lies would break her heart, the Penguin looked her in the eye and denied it. Putting a rift between them that hadn't mended before Gertrud was murdered. Fish's declaration of love set the Penguin free all over again. 3) 03x22, 'Heavydirtysoul'.
This is the first time that the music plays with a totally self-assured Penguin on screen, the first time that he is the one reading the other party to rights ("I know you, Ed. I may be driven by my emotions, but you are driven by something much more predictable..."), and the first time that he turns his threat to destroy into a fulfilled promise. "Destroy" in this case does not mean "kill." Kill would not be sufficient revenge for what the Riddler put Oswald through: unrequited love first, and a betrayal that almost killed him later. Both are galling. The final, ultimate stress test for the Penguin's survivability as a boss who draws strength from loving nobody and anticipating any betrayal - the very code that Ed recommended Oswald adhere to. But by now, Oswald has grieved his mother, whose body he cradled while crying. Penguin cried and cradled Fish Mooney's body in the exact same way when she died. Gotham's version of this character might be the first Penguin who was attracted to men, but he was certainly not the first Penguin to have his villainous transformation cemented via an attraction turned violent. In this scene, he has Ed frozen alive, telling him "I want you around as a constant reminder to never make that mistake again." The Riddler becomes an owned ornament in the Iceberg Lounge. His own belief in his ability to disorientate others with the "exacting fashion" of a well-planned puzzle has been flattened by the Penguin outwitting him. Most visceral of all, Oswald does not identify Ed as an active agent in his decision to never love anyone. The profundity of Ed's words about Gertrud in Season 2 is voided, because the Penguin implies (correctly) that his love for his mother never had that power. Oswald says Ed was the "only time I let love weaken me"; the Riddler prides himself on deliberateness, but the most influence he ever had on Penguin was accidental. In three acts, over three confrontations, Oswald's transformation became complete. Nygma truly did free Penguin's mind.
The beautiful irony of that last instance is that Oswald manages to convince Ed that he's been fully defeated, that he's less than nothing to Oswald and completely at his mercy (and the analysis above of how Oswald systematically crushes Ed's conception of his own power and brilliance is spot-on)... but I think we all know that the real reason Oswald has him frozen rather than killing him is that he's still in love with him and can't bear to kill him. This, predictably, opens him up to new vulnerabilities: the frozen centerpiece he had publicly advertised is stolen from him, and then Ed starts publicly mocking him in the Narrows, both of which weaken his reputation and credibility. He tells Ed he's keeping him around as a reminder to never let love weaken him again, and Ed believes him; but in fact, in the very act of keeping him around, he is already continuing to let love weaken him.
Late response but @philosopherking1887 you were unfathomably correct for this
