I am a dissapointment to my family

Oswald surveyed the wide expanse of the Iceberg Lounge with the same casual control of a French monarch maintaining the attention of his court. No amount of the expensive cologne which studded his thick frame ever seemed enough to overpower the scent of alcohol and much cheaper colognes which sat heavily in the air. He had once considered pumping some kind of scent through the vents but given Gotham’s affinity to gas-based attacks, it was decided such a thing would incite panic rather than gratitude.

The Iceberg Lounge was his kingdom and he ruled with an iron fist. One which puppeteered the various bouncers, each with their own body count and an NDA so tight that they would never dream of speaking ill of their employer, with ease. Currency was the law of the land and anyone capable of paying their way was more than welcome.

As Oswald swept through the Lounge, his expensive suit making as much of an impression as his steeled spine, he ignored the throng of spectators – the ones who only paid his extreme entry fees to catch a glimpse of the famous Penguin. Quickly finding the object of his desire, the man whom he had dragged himself from his office to specifically seek out, he discovered Edward laying sprawled out comfortably in Oswald’s own private booth with very little care for any of the circus which boomed around him.

“Are you enjoying drinking my bar dry?” Gently brushing a thick hand across his hair, ensuring that the strands were still pushed back and showing their best, Oswald peered down at the splayed figure with irritable fondness.

“Your bar is running out of that delicious London gin which I favour,” Edward replied without missing a beat. “Is the Penguin losing his touch and unable to pay the bills this quarter? I can loan him some money if needs? I can spare some change to keep my liver accustomed to a certain standard.”

“That cheeky mouth will get you in trouble, Eddie.” Oswald curled his lips into a dangerous smile, in equal parts delighted and furious with the easy tease. “I’ve only just left my office. If I have to drag you back up there to remind you of how you talk to me within these walls then I’ll make sure it was worth my effort.”

“Perhaps that’s exactly what I want you do and you’re playing into my hands. C’mon, Ozzie, we both know you like sitting down here and watching the denizens gawk at us like circus animals. They come for a Penguin and leave destitute. It’s a fair price in my humble opinion.”

“You’re projecting. I don’t care about their greedy eyes.”

“Maybe I am,” Edward confessed as he carefully brushed the skin below his eye in such a way that he did not disturb the faintly smudged makeup there, “but then again, I can easily place blame on the trio of gins I have enjoyed waiting for you to grace me with your presence.”

Chuckling as he dropped to his usual position in the both, Oswald waited for Edward to right himself and adopt a similar seated position as they both stared out across the Lounge – two pairs of intelligent eyes taking in different aspects of their environment.

However, whatever casual enjoyment Oswald was looking forward to as part of his easy night was smothered in an instant by the appearance of a dark shadow which invaded his private space.

Eyeing up the intrusive figure of Roman Sionis as he approached and slid himself across the other side of the table, quickly making himself comfortable in the booth with an unbridled show of arrogance, Oswald nudged Edward’s knee with his own as he drew his attention to the unwelcome addition.

“I think Sionis wishes to conduct some business with us this evening.”

“Tell him to fuck off.” Edward answered, quiet enough for only Oswald to be able to pick the words over the thrum of the band which Oswald had hired for the evening entertainment. An aspiring guitarist with big dreams, he had caught Oswald’s ear one night as he attended a neutral meeting with the other crime bosses and Oswald had been quick to snap him up with a more than handsome offer.

“Edward,” Oswald warned, his voice dropping the same octave it always did when he wanted to impress onto Edward just how short his temper was at that particular moment, “please, move and join me properly so we can talk business with our guest.” Speaking the remainder of his words with greater volume, he clued Roman in to their discussion with a charmless smile.

Reading between the lines of Oswald’s words, Edward stood to his feet and shifted closer to his partner, careful not to knock over any of the painfully expensive drinks which lined the table as he adjusted himself.

“Yes. I think I would like to discuss some potential work with Nygma if that’s,” pausing to consider his words carefully, Roman reclined in his chair as he picked up the glass of scotch which he had only just deposited on the table to watch Edward move, “allowed.”

Dropping into Oswald’s lap, Edward made himself comfortable as he hung his long legs off the side of Oswald’s thighs. His hand immediately made itself home on his chest in a familiar show of casualness, thin fingers brushing across the mat of exposed chest hair which poked free of Oswald’s opened shirt as Oswald’s visibly sank into the effortless touch.

Wrapping an arm around Edward’s waist, the thin silken material of his shirt feeling delicious against his thick fingers, Oswald made a point of settling his hand on the upper part of Edward’s thigh – practically his groin – as he refused to break eye contact with Roman.

“What do you think, Edward?” Oswald asked, a hint of something dangerous luring behind his jovial, charmed expression. “Are you interested in discussing business with Mr. Sionis here?”

Edward’s brilliant green eyes glittered their intelligence as he surveyed Roman with a graceless smile, “As always, you want to use me to bolster your position within the underworld and who could blame you? My name carries a certain,” Edward paused as he placed a hand on the swell of Oswald’s gut, “weight which would benefit anyone whom I chose to align myself with. But I will have to decline whatever offer you think you can make.”

“You don’t even-” Roman started, ready to fight the point but quickly found himself cut off by Oswald.

“This mouthy little peacock does not work for anyone who moves against me, Roman. You know that.” Oswald accused openly, fearing nothing while within the walls of his sanctuary. “Why bother trying to ruffle my feathers over something so trite when we both know you are positioning yourself to advance across the southern docks?”

“I would never move against you, Ozzie. We’ve also been friends for a long time, you and I. I’m only asking if Nygma would like to earn a pretty dollar for a little side project I am looking into.”

“Is Roman your friend?” Edward asked.

“Sometimes,” Oswald answered. “Mostly when it suits him. Or when he senses benefit. It seems to be a reoccurring theme around here.”

Edward made a low humming noise but said nothing further as he pushed his red hair behind his ears, the soft motion exposing the lurid green question-mark shaped earrings which sat daintily against his lobes – the earrings studded with enough real emeralds to make a jeweller blush. He looped an arm around Oswald’s back, angling his hand so that it could easily reach the soft hairs which littered the nape of Oswald’s neck as he teased the sensitive area and enjoyed how it stiffened the thick body which housed him.

Oswald pulled his hand from Edward’s thigh, quickly wrapping his fingers around the soft skin of Edward’s chin. With his missing pinkie leaving a gap against the skin, he instead focused on stroking his thumb along the defined edges of Edward’s jaw – something flashing in his gaze as he felt Edward sigh and sink into the gentle touch as he continued.

“Roman, my associate here has, again, expressed no interest in joining any of your schemes.” Oswald stated, his voice jovial but with glacial undertones as a passing waitress subtly signalled to ask if he wanted any refills. Giving her a sharp nod, she shuffled off to fetch the drinks as Oswald returned his gaze to Roman. “I keep him far too busy to indulge any other potential clients.”

Never content to be spoken about without his own input, Edward tactfully rolled his fingers along the silken edges of Oswald’s shirt while pretending that his constant brushing of the chest hair there was accidental at best.

“I’m positively a slave.” Edward teased, deliberately shifting his ass across Oswald’s groin and forcing a twitch of irritation at the display to flit across Roman’s expression. “But, a truth is a truth, and if the infamous Black Mask wishes to talk business with the Penguin then I will excuse them from my booth and insist that business is conducted upstairs.”

“Your booth?” Oswald murmured, his brow cocking behind slightly shaded glasses as he fixed Edward with an indignant look. “In what world?”

Laughing softly at the challenge, Edward swept himself from Oswald’s lap with grace as he slipped back to his original positioning on the curved seat of the booth.

“I will have a selection of meats and cheeses delivered here within the hour.” Thrumming his fingers on the edge of his gin glass, Edward held Oswald’s eye as something unspoken passed between them. “Try to return within that time and not allow them to go to waste.”

With Edward giving him an easy out from a long, drawn-out discussion with Roman, Oswald flashed sharp white teeth in the dimness of the secluded booth.

“I wouldn’t dare,” Oswald tilted his head as he turned his attention back to Roman, “but my peacock is correct. Our business will conclude within my office and then I will come back here while you leave to return to whatever strip joint you have most recently thrown your name behind.”

Swallowing the shameless disrespect with a forced smirk, Roman’s eyes darkened as he stood from the booth, gave Edward a stiff nod, and slowly made his way towards the back stairwell.

“I hate him.” Edward grunted as he watched Roman leave.

Oswald, feeling much the same but having heard Edward’s distaste for the man lamented many times over their shared years, simply sighed.

“I know, Eddie. Believe me, I know.”

First off, I know that the writers did an actual reference there and based him off Tommy Udo in Kiss of Death, a noir film Frank Gorshin was taking inspiration from for his Riddler portrayal in the 60s.

I don't really care. It's a neat reference, but a character needs to be more than just an in-joke if they get this much screentime. Joker is a good example. He's based off Conrad Veidt, he's a serious, grim Joker who smiles but hardly laughs-- but he still uses Joker gas. He likes endless nihilism, he's a sadist, he still feels like the Joker. A dour, noir Joker, but still the Joker.

Riddler?

Guy says one pineapple grenade joke and then goes back to shooting people. He's an idiot. He's not the Riddler. He's Black Mask in Riddler's clothes.

I'd like to compare this to the other Caped Crusader villains. Did they make Harley not a psychiatrist? No. Did they make Gentleman Ghost not rob people and not be a ghost? No. Did they make Penguin not a crime boss, even when they genderswapped her? No!

Why did Riddler get an entirely new personality and new job and lose his gimmick outright? If it was just one or the other it could even work (it's a thing in Caped Crusader to switch motives or personality) but the problem with Riddler is that they lost his gimmick too, the one thing all other antagonists kept.

It makes him feel empty, because without the cerebral mind games he's basically just a mobster movie archetype. The Nicky from Casino. The Tommy DeVito from Goodfellas. Tony Montana without the redeeming qualities. The hothead who feels invincible and dies because of his own hubris.

Which if you've seen any actual mobster movie, has probably been done better in anything else you've seen, because it's not crammed sporadically in ten episodes. And because those mobsters probably had more interesting dialogue, because they'd often get some wit. This Riddler? Zilch.

When Riddler is around, the mobsters have left Gotham. He's a post-supervillain arrival, he's not a Falcone. The Falcones are a shoe-in for mobster movie archetypes too, but they don't put Carmine Falcone in a lizard coat and say he's Killer Croc because that subverts your expectations!

There's just nothing to Riddler besides the mob archetype. How interesting is he as a character, by himself?... uh, he's stupid and evil and even more evil and so one-note that he just gets shot and dies in Episode 7 because Joker needed that extra screentime to do something actually interesting.

What makes him special? The fact that he'd kill all friends? The fact that he's brutal and rules his new empire on his own whims? That's... not a unique personality. That would probably be the same as Oswalda with more bullets, and Oswalda got her gimmick in her water emphasis, which set her apart from just being another mobster.

Taking away Riddler's gimmick isn't just removing a funny voice and 'Riddle me This!' scene, it's literally stripping him of anything to distinguish himself from just another goon with a gun.

What maddens me more is that he could still be a mobster, the idea of him being a mobster isn't bad, it's that they took the most boring way out of it! When I say they took the wrong inspiration from Casino, I mean he should be an Ace Rothstein, or to use a real-life (more real life, Casino is based on real life) example, Meyer Lansky.

If they wanted to do a Riddler, he should've been a numbers man, an organizer. A mobster who keeps the books running, the cash rolling in, and everything in tip-top shape in the pyramid.

He should be called the Riddler because he orders people 'riddled' with bullets, not because he is the one riddling people because that also makes Thorne look like a moron for putting him in any authority for longer than twelve seconds.

How much more into the gimmick would that be? Infinitely! He could get frustrated at Batman knocking down his pyramid of crime, then suddenly chomping at the bit to be more involved with 'the Bat' because he's finally got a match with his brains!

Mobsters aren't known for being smart! Mobsters are often people who go into crime because an actual, societally-benefitting job isn't in their interests!

No wonder a different version of the Riddler would be obsessed, because for once someone gets his obscure book references, for once he has someone who can pick up wordplay, because they didn't quit fifth grade to harass shopkeepers.

For once he has met someone in his line of work that has more than just a trigger finger, an actual brain, and a sharp one, an educated one!