"Birds of a Feather," which features the Penguin, has its roots in the disgusting Penguin character that Danny DeVito originated in Tim Burton's Batman Returns. Wikipedia goes into detail as to how he was portrayed:
While this Penguin retained many trademarks, such as a variety of trick umbrellas and the use of a monocle, he was given a dramatic visual makeover. Where the comic version varies between a balding head of short cropped hair and varying degrees of thinning, this Penguin is still bald at the top but with his remaining length of hair long and stringy. His hands are flippers with a thumb and index finger, and the remaining three fingers fused. An unidentified thick, dark green bile-like liquid sometimes trickles from his nose and mouth. Instead of a tuxedo, he wears a more gothic, Victorian-style outfit with a jabot as opposed to a bow tie. In certain scenes, he also wears black boots, a dickey, and a union suit. However, Burton's design maintained the top hat seen in the comics along with a monocle and a cigarette in some scenes. He also has penguin-like appetites, as shown in a scene where he devours a raw fish.
Batman: The Animated Series was strongly influenced by Burton's films:
This version of the character featured the film version's physical deformities, such as flippers and a beak-like nose, but he retained the traditional refined mannerisms and personality of his comics counterpart.
With all this in mind, "Birds of a Feather" considers the possibility of a reformed villain. As a hybrid character, the animated incarnation of the Penguin is a combination of two very jarring archetypes that don't blend well together. The Penguin is a character with aristocratic tastes who is also repulsive, and "Birds of a Feather" is fearless in examining what that holds for his reentry into civilian life.
Characters like the Riddler and Clock King can easily blend in with society if they so choose; this unique incarnation of the Penguin cannot. If he was the more human-like Penguin he could have more smoothly reintegrated; if he was the more brutish mutant from the films he wouldn't have the same aristocratic ambitions. This tragedy (and make no mistake, the plot is a tragedy on many levels) is unique to the animated version of the Penguin.
Rich socialite Veronica Vreeland decides that the best way to spice up her party is to invite a criminal to it. The Penguin is charmed by Vreeland's attention and is duped into believing her affection is genuine. Tragically, Vreeland's affection DOES eventually turn genuine, but by then it's too late-- the Penguin's rude treatment by the elite causes him to revert to his criminal ways, kidnapping Vreeland and demanding a ransom.
Bruce Wayne witnesses much of this and, despite warning Vreeland that her false pretenses is a bad idea, does nothing to stop her. In his guise as Batman he also misreads the Penguin as a villain when the reformed bad guy manages to fight off muggers (to defend Vreeland). Again, Batman doesn't give Penguin the benefit of the doubt. Or to out put it another way, Wayne is witness to twice as many examples of Penguin's sincere attempts at reform...and is therefore doubly damned for not intervening.
Wayne does nothing to help the Penguin at social parties, and Batman does nothing but threaten the Penguin when he's out of jail. It's a common theme in the comics for psychologists to question if Batman causes more problems than he solves, and "Birds of a Feather" comes down soundly against the Dark Knight.
Chuck Menville (his final story, aired posthumously after his death a year earlier) slyly has the Penguin use the opera as his villainous lair, in this case the role of Canio in I Pagliacci. In Pagliacci, the buffoonish clown Canio, like the Penguin, is deceived by a woman putting on an act for an audience, and when he discovers the ruse uses the theater to enact his vengeance. It's a brilliant bit of meta-narrative.
The Penguin's frustration is portrayed cartoonishly as he wails and pounds his fists, but there is nothing funny about what "Birds of a Feather" espouses. TVTropes says it best:
The episode title is "Birds of a Feather", but the whole saying is: "Birds of a feather flock together". However, this is not the case: Oswald Cobblepot, Veronica Vreeland, Pierce and Bruce Wayne all are Ineffectual Loners with a touch of the Sad Clown. Even when united by his petty delusions, (Veronica, Pierce and Bruce are in the same circle, but they cannot communicate well with each other) these Birds of a feather flock alone.
The only person who seems to genuinely understand (and is disgusted by) what's going on is Commissioner Gordon, who isn't one of the upper class. That's telling. Menville squarely places the Penguin's villainy on the rich, and by proxy Bruce Wayne's wealth (and his Batman persona) are thus part of the problem.
After this episode, the Penguin's plans turn more brilliant (he tracks down Batman's mechanic by monitoring automotive orders for the Batmobile) and ruthless (he uses a military helicopter to blow up a bridge with civilians on it). And yet I can't help but feel that if the Penguin had just been treated like a decent human being, much of the later destruction could have been avoided. All the property damage and death he caused afterward is on Vreeland and Wayne's shoulders.
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