The depictions we've seen in recent years, alas, don't quite get him.
I don't disapprove of the depiction of Oswald as smart, savvy crime boss, pulling strings behind the scenes while he poses as a Legitimate Businessman; the role suits him like a well-tailored tuxedo. Unfortunately, as the Batman titles move away from Theme Villains who treat Crime as Performance Art, there's a tendency to sweep that period under the rug entirely. Cobblepot is now a Clever, Devious Gangster, and one gets the impression that he has always been a Clever, Devious Gangster.
Fiction, however, suffers no lack of Clever, Devious Gangsters, nor does Real Life. Everyone knows they're Connected. Everyone knows they've got their Fingers in the Pies. Nobody can get any hard evidence, or pierce their thin veneer of Legitimate Business to bring their nefarious deeds to light.
It's a complex and multifaceted character archetype, admittedly, but it's a common one—and if there's one thing that Oswald Chesterfield Cobblepot strives never to be, it's common.
Without her career as Batgirl behind her, Oracle is just another hacker. Without his career as a Theme Villain, Oswald "The Penguin" Cobblepot is just another Made Man, differing from Rupert Thorne or Tony Zucco only in his nom de guerre—and his real-life peers include such notables as "Baby Face" Nelson.
To me, the Theme Villain and the Clever Devious Gangster are two sides of the same Penguin coin.
Golden Age Oswald had one of the best origins in comics: he got no respect because he was, frankly, a funny-looking little fat guy with mildly eccentric habits. He deliberately constructed the Penguin persona, exploiting and accentuating his comical appearance, encouraging people to underestimate him.
He pulled off big, flashy, ridiculous stunt crimes, deliberately provoking
the local costumed vigilante, because that's how it's done in Gotham.
And it worked.
He made his rep as the one Flashy Theme Villain who was Smarter Than He Was Crazy.
When he walked into a room, people no longer thought, "what a funny little man!"
They thought, Holy crap, it's the Penguin!
His "Crime as Performance Art" routine paid off. He got respect.
And he parleyed that into the criminal empire we see today, in the Aluminum Age.
Now, there's a unique character.
I'd love to see a Penguin graphic novel that shows his evolution from Performance Artist Gimmick Villain to Criminal Mastermind. He slowly and quietly builds up his organization—and every time the Bat starts getting too close to his real operations, he puts on the tux and the top hat, grabs a bumbershooter, and pulls off some big, flashy, incredibly distracting Stunt Crime.
He's thwarted, captured, tossed into prison, and uses his prison time to make more contacts and connections. He serves a short sentence, since he studiously avoids injuring or killing anyone in his big stunt crimes, and might even get time shaved off his sentence for "good behavior": he keeps his prominent nose clean when he's inside.
Eventually, he "goes straight", opening the Iceberg Lounge and putting himself on display as Supervillain Chic. He writes his memoirs, and does the talk show circuit, openly talking about his "misspent youth", freely admitting that his "Fine Feathered Felony" was, in essence, a publicity stunt to garner the respect and recognition that he so craved. He's witty and charming and funny and a great draw.
And in the background, though layers of front companies, bribes, and shady connections, he runs a good chunk of the Gotham City underground.
*Aren't these Thornes and the Zuccos of the world the ones that the Batman is supposed to focus on? Isn't he the Great Detective who can get the goods when nobody else can? They used to be disposable mooks, soundly defeated and sent up the river; nowadays, they seem even more untouchable in Gotham than their real-world counterparts. I need to do a post about the "Batman is Useless" trope, and how it really only emerged Post-Silver Age.