View Full Version : Best Penguin Stories?
JerryvonKramer
08-08-2008, 06:22 AM
What the are best Penguin stories or TPBs/ arcs that strongly feature Penguin?
I ask this for 2 reasons: 1. I'm currently buying lots of TPBs and 2. To consider what sort of stories Nolan could mine for Batman 3.
shaxper
08-08-2008, 08:38 AM
I've never felt that Penguin held his own as a Batman villain. He's a cookie-cutter Dick Tracy villain through and through -- mob boss with a defining physical deformity from which he gets his name. There really isn't much more to the guy beyond the gimmicky umbrellas. I supposed Paul Dini has written him best in his current Detective Comics run, but I wouldn't expect him in a Nolan film anytime soon. Anything Tim Burton added to the guy in Batman Returns was strictly his own invention, not based on the comics.
Schornforce
08-08-2008, 09:39 AM
The Penguin issue of the very recent Joker's Asylum was very good. One of the best of the mini series.
Also, I remember liking 'Penguin Triumphant' which came out around "Batman Returns"
rwe1138
08-08-2008, 10:15 AM
He had some good stuff during No Man's Land. And I love how Dini's used him in Detective.
jgiannantoni05
08-08-2008, 11:06 AM
To me, the best Penguin story is Detective 610 and 611 "Snow and Ice" by Alan Grant and art by Norm Breyfogle.
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The Batman
08-08-2008, 11:17 AM
I thought Penguin Triumphant was pretty enjoyable too though its been ages since I've read it. There was a couple of good Grant/Aparo/Breyfogle Penguin stories in the late 80s early 90s too - "The Penguin Affair" and the two-part "Snow and Ice" which was a "Death of the Penguin" story that ran in Detective Comics.
http://www.coverbrowser.com/image/detective-comics/610-20.jpg
There was also that one episode from the Animated Series "Birds of a Feather" which manages to make you feel bad for old Oswald.
The Batman
08-08-2008, 11:28 AM
As for Nolan and the Penguin, should the former ever decide to use the latter in a movie, I imagine that he'll need to alter him as much as he did the Scarecrow or the Joker to fit into his world.
"Who's Cobblepot?"
"I'm Cobblepot you cretin! Do you think my parents named me The Penguin?"
I think from Detective Comics 683 - Chuck Dixon
"When you see Batman, who do you see him with? Criminals! When you see me, who am I with? The police! Because I'm helping them!"
Burgess Merideth Batman TV series
I also highly recommend the excellent Grant/Breyfogle two-parter from Tec 610-611. There's a similar theme in Brave and the Bold 191 in which The Penguin apparently dies at the hands of the Joker, but that's more of a Joker tale.
Here are two recommendations that portray Oswald Cobblepot as an ingenious, sympathetic character, who you can believe that if he really put his mind to it, would be brillant at anything he attempted.
Secret Origins Special 1 (1989) - it's an all Batman rogues issue so you'll also get a Riddler story which was frequently mentioned in the recent 'What are the best Riddler stories' thread and a great Two-Face story in addition. The Penguin tale however, is my favorite out of the selection of stories and is written by Alan Grant and drawn by Sam Keith.
The Penguin abducts a criminal while he's being transfered to another state to attend his father's funeral. The criminal is known to The Penguin as his relentless tormenter from his childhood. Cobblepot refreshes the man's memory of those days - of the abuse he suffered; of his first being called the Penguin due to one of his infinite pranks; of the day when he stood up to his abuse and beat him senseless; and of the afternoon following in which the bully retaliated by killing everyone of his birds. The wit, arrogance, brillance, and even charisma The Penguin displays in this story makes it a hard one to beat.
Batman Annual 11 (1987) - Better known for the Alan Moore Clayface story which opens this annual, the Max Allan Collins/Breyfogle Penguin story is sadly underrated.
The story opens with a parole board deciding whether or not Oswald Cobblepot should be released from prison. Batman appears before them pleading that they keep him locked up. In a humourous scene, the board tells Batman that they're not likely to take the word of a masked vigilante too seriously which only leads to Batman storming out of the room as Robin asks how things went. The Penguin is released and Batman is skeptical, but he knows that Cobblepot's up to something. When the Bat-signal is shone the next evening, Robin wonders if it's about the Penguin. Batman scoffs "I hardly think Gordon would call us in on a routine matter" When he arrives at Headquarters and asks what the Commissioner wants he's told "Just a routine matter...rash of liquor store robberies".
Batman however, can't shake the feeling that the Penguin is up to something and sure enough discovers that he's been secretly contacting some of his old cronies and has been doing something in an old Umbrella factory in Gotham. He's also been wooing a woman he had met as a pen pal while in prison who Batman approaches. Before he can get a word in, she yells at him for tormenting her Oswald simply for "collecting" valuable items. "What you call 'collecting' I call 'stealing', but you have my word that he'll only get my attention if he deserves it". So the Penguin's new found love tells Batman that he strikes her as honourable and will take him at his word.
That night Batman and Robin stake out the Penguin's Umbrella Factory and wonder why a reputable business needs armed guards. A closer look reveals those guards and everyone there as former henchmen. They enter and a fight ensues which the Penguin doesn't get involved. When he tells Batman that the business is in fact reputable, Batman asks about the armed guards. The Penguin responds that it's to keep prying eyes out. Batman finds this suspicious and asks what he doesn't want people to know. The Penguin sadly tells him that he felt that everyone deserves a second chance and as such, rehired his former henchmen and offered them an honest job. Unfortunately, this as Batman sadly remarks "puts him in violation of parole". The Penguin is rejailed and despite Batman's pleas to the parole board that he be released, his wishes are once again ignored. The Penguin is despondent that he's lost his freedom and more importantly, the love of his life. Teary-eyed about what he's lost, he's seen sitting in his cell thinking about his girlfriend when he's told he has a visitor. It's the woman he thought he had lost who's here to tell him that she's accepted his marriage proposal. "You recognize that my heart was in the right place? But how?" "A little bat told me".
The Greatest Batman Stories Ever Told tpb from 1989/90 contains two Penguin stories - a newspaper strip from the 40's and a team-up with the Joker in which the two compete to prove who is the number one villain in Gotham. I recommend both of these stories as well.
JerryvonKramer
08-08-2008, 05:05 PM
Thanks guys, some excellent posts there.
Are any of these stories collected anywhere?
I'm not really into collecting single comics, only TPBs. I'm from UK by the way, even stuff like "Stacked Deck: Greatest Joker Stories" can be tough to track down (not a single copy on ebay). We don't really have that many comic book stores here either, save the big Forbidden Planet in London. I think comics have always been much bigger in the States than here. Well, I guess we have Beano and stuff like that, but I mean the DC/ Marvel stuff.
foxley
08-08-2008, 08:35 PM
Thanks guys, some excellent posts there.
Are any of these stories collected anywhere?
I'm not really into collecting single comics, only TPBs. I'm from UK by the way, even stuff like "Stacked Deck: Greatest Joker Stories" can be tough to track down (not a single copy on ebay). We don't really have that many comic book stores here either, save the big Forbidden Planet in London. I think comics have always been much bigger in the States than here. Well, I guess we have Beano and stuff like that, but I mean the DC/ Marvel stuff.
As Chad said, several of these stories were collected in The Greatest Batman Stories Ever Told, Vol. 2
http://www.comics.org/graphics/covers/25748/400/25748_4_002.jpg
Dr Cthulwho
08-09-2008, 06:30 AM
I thought Penguin Triumphant was pretty enjoyable too though its been ages since I've read it. There was a couple of good Grant/Aparo/Breyfogle Penguin stories in the late 80s early 90s too - "The Penguin Affair" and the two-part "Snow and Ice" which was a "Death of the Penguin" story that ran in Detective Comics.
http://www.coverbrowser.com/image/detective-comics/610-20.jpg
There was also that one episode from the Animated Series "Birds of a Feather" which manages to make you feel bad for old Oswald.
I always liked that cover. I think because at the time I thought "forget a weeping Angel, when I die I want a Penguin headstone."
JCAll
08-09-2008, 08:04 AM
Has the recent Gotham Underground mini been put to trade yet? Most ofit was mediocre, but the Penduin bits were fantastic. Expecially his conversations with the Riddler.
Tony Bang
08-09-2008, 08:11 AM
The only thing that comes to mind when I think of the Penguin is the 60's show and movie. So I'd go with the Penguin stories found in the Showcase Presents books.
Nothing like what Nolan would do with the character, but fun stuff.
rwe1138
08-09-2008, 09:46 AM
Has the recent Gotham Underground mini been put to trade yet?
Not yet. (http://dccomics.com/dcu/graphic_novels/?gn=10380)
newrose
08-09-2008, 11:40 AM
Thanks guys, some excellent posts there.
Are any of these stories collected anywhere?
I'm not really into collecting single comics, only TPBs. I'm from UK by the way, even stuff like "Stacked Deck: Greatest Joker Stories" can be tough to track down (not a single copy on ebay). We don't really have that many comic book stores here either, save the big Forbidden Planet in London. I think comics have always been much bigger in the States than here. Well, I guess we have Beano and stuff like that, but I mean the DC/ Marvel stuff.
You can find a Forbidden Planet store in most cities in the UK. http://www.the-master-list.com/International/United_Kingdom_&_Ireland/index.shtml has a list of all stores in the UK. may be a couple of years old but it is accurate.
The Beast Of Yucca Flats
08-09-2008, 04:30 PM
Ed Brubaker had some cool stories with him in his first 5 or so issues of Batman.
I think the Penguin works better now as a character than ever before. Cobblepot has pretty much been a member of the Bat books somewhat regular supporting cast for quite a few years. As a character, they seem to use him to find out information or villains often go to him as a fence. I've liked the Iceberg Lounge idea and how they have developed his character out over the last few years. I like the idea that while he is odd and very vindictive, he is not flat out nuts like most of the Bat rouges.
JulianPerez
08-09-2008, 06:21 PM
I'm surprised nobody has mentioned Englehart's "Malay Penguin" story. If you only buy trade collections, you're in luck: I don't think the Englehart run has ever been out of print, particularly in the recent "Batman: Strange Apparitions" comic.
The great part about the Malay Penguin story was how it showed that, despite the Penguin's funny looks, he's not a funny little man: he's a very skilled criminal mastermind and planner, but one that, like the Riddler, plays "fair," according to certain rules that define his capers. The Penguin has a hammy theatricality as well, and an obsession with birds.
JerryvonKramer
08-09-2008, 06:43 PM
As Chad said, several of these stories were collected in The Greatest Batman Stories Ever Told, Vol. 2[/IMG]
Actually, I've got Greatest Batman Stories vols 1 and 2, and none of these stories are in there. "Penguin Affair", Secret Origins Special 1, and Batman Annual 11 certainly aren't. I read somewhere that the Secret Originis story is actually in "Featuring Twoface and Riddler" is that right?
I'm surprised nobody has mentioned Englehart's "Malay Penguin" story. If you only buy trade collections, you're in luck: I don't think the Englehart run has ever been out of print, particularly in the recent "Batman: Strange Apparitions" comic.
The great part about the Malay Penguin story was how it showed that, despite the Penguin's funny looks, he's not a funny little man: he's a very skilled criminal mastermind and planner, but one that, like the Riddler, plays "fair," according to certain rules that define his capers. The Penguin has a hammy theatricality as well, and an obsession with birds.
YAY, "Strange Apparations" is one of the ones I've got coming through the post, so I look forward to that.
Actually, I've got Greatest Batman Stories vols 1 and 2, and none of these stories are in there. "Penguin Affair", Secret Origins Special 1, and Batman Annual 11 certainly aren't. I read somewhere that the Secret Originis story is actually in "Featuring Twoface and Riddler" is that right?
YAY, "Strange Apparations" is one of the ones I've got coming through the post, so I look forward to that.
I refered to The Greatest Batman Stories volume one not as a means through which you'd find the two stories I recommended, but to find the newspaper Penguin appearance from the 40's and the Joker/Penguin team-up from around the same time.
The one foxley cited dates back to the second Keaton film and was released as a tie-in. I don't know what's contained there-in since I've never owned it.
There's a bit of a catch though. DC has recently released two Greatest Batman Stories Ever Told editions which have little in common with the original editions. If your copies have a painted Alex Ross covers the new ones are the ones you own.
That Secret Origins Penguin story wouldn't be in the Two-Face/Riddler tpb (which I'll bet is called The Greatest Batman Stories Ever Told volume 3) but the Riddler and Two-Face stories in that same issue almost certainly are. If the Penguin Secret Origins story has been reprinted anywhere, it'll have been in the tpb foxley recommended. If it isn't in there, my guess is you'll have to buy the original comic itself to find the story.
JerryvonKramer
08-09-2008, 07:25 PM
Chad, I've got the old Greatest Stories ones. My vol. 2 has Penguin and Catwoman on the cover.
I have it right here, Penguin-related contents:
"One of the Most Perfect Frame-Ups", "The Penguin's Fabulous Fowls", "Partners in Plunder", "Penguin Takes a Flyer into the Future", "Hail Emperor Penguin", "The Malay Penguin" (!!!!! YAY!), ""Love Birds" (from Batman Anual 11!! YAY!), "Eyrie".
Maybe I should have opened this before making this thead! :tongue:
Also, look at this: http://www.mikesamazingworld.com/tpbs/list.php?group=batman&choice=twofaceriddler
Is "The Killing Peck" that Secret Origins Penguin story? Wonder why it's in a Two-Face/ Riddler book.
I've also got the 1989 Greatest Stories (vol. 1), I've read the two stories to which you refer. The one with Penguin's aunt is moderately amusing but I don't really like that goofy period after about 1943. Batman and Robin do stuff like randomly talk in rhyme. I'm quite tolerant of Silver Age stuff as a whole, it's just that little period in the mid to late 40s after Robin first emerges. The writing is just horrible in some of stories -- is it Kane?
Chad, I've got the old Greatest Stories ones. My vol. 2 has Penguin and Catwoman on the cover.
I have it right here, Penguin-related contents:
"One of the Most Perfect Frame-Ups", "The Penguin's Fabulous Fowls", "Partners in Plunder", "Penguin Takes a Flyer into the Future", "Hail Emperor Penguin", "The Malay Penguin" (!!!!! YAY!), ""Love Birds" (from Batman Anual 11!! YAY!), "Eyrie".
Maybe I should have opened this before making this thead! :tongue:
Also, look at this: http://www.mikesamazingworld.com/tpbs/list.php?group=batman&choice=twofaceriddler
Is "The Killing Peck" that Secret Origins Penguin story? Wonder why it's in a Two-Face/ Riddler book.
I've also got the 1989 Greatest Stories (vol. 1), I've read the two stories to which you refer. The one with Penguin's aunt is moderately amusing but I don't really like that goofy period after about 1943. Batman and Robin do stuff like randomly talk in rhyme. I'm quite tolerant of Silver Age stuff as a whole, it's just that little period in the mid to late 40s after Robin first emerges. The writing is just horrible in some of stories -- is it Kane?
No idea why a Penguin story is reprinted in that Riddler/Two-Face tpb but you're right, The Killing Peck is the one I recommended. I guess the story is simply that good.
It's too bad you didn't like the older Penguin stories especially since if those weren't to your favour then there isn't likely much prior to the Silver Age that you'll find to your tastes.
Eyrie is one that like The Malay Penguin should probably have been recommended. I say 'probably' only because it's been awhile since I've read it. I have an impression that it's quite good though.
Let me know what you thought of the other two.
JerryvonKramer
08-09-2008, 08:11 PM
I've been reading through Vol. 1 Chad, and I'd say that 1939-42 is ok, if a little clunky. The Hugo Strange story by Bill Finger is good, but I don't like Fox Gardner as a writer -- he just doesn't understand how to use language properly. Mid-late 40s is fairly amusing -- kinda reminds me of the old Filmation cartoons (rather than the Adam West series) in terms of tone and colour -- but I simply don't understand why they break out into rhyme. The scene in which Penguin and Joker argue about who's the best criminal is pretty good, but there's just too much ... heavyhandedness for me to love it.
I've actually found the 1950s stories in the '89 book with Dick Sprang artwork pretty good. "Origin of the Superman-Batman Team" in particular.
I'll let you know what I make of the Penguin stories in Vol 2 here Chad. :biggrin:
Incidentally, did they stop using Super Villains in the 50s and 60s? Why do the likes of Penguin and Riddler disappear for so long?
JerryvonKramer
08-15-2008, 02:11 AM
I read "Partners in Plunder" (Batman #169, 1965) last night.
That's a great little Penguin story (in his second Silver Age appearance).
I think they did a version of this on the Batman '66 show. Basically, Penguin can't think of a decent crime, so he plans a load of random, unrelated umbrella-related stunts across Gotham and then puts a bug on Batman. The masterplan being: Batman will connect the dots and come up with the perfect plan himself and provide the blueprint.
It's GENIUS, the Penguin outmanouvres Batman and makes a fool of him at the same time. Not only that, it suggests that Batman has the mind of a master criminal! I'd chalk that up as a Penguin victory (as he does). This is how the Penguin should be written: someone who is clever enough to let Batman trip up on his own intelligence. He's got a different sort of intelligence to someone like the Riddler, it's more "tricky" and this story exemplifies it.
Highly Recommended! Mine is collected in The Greatest Batman Stories Ever Told, vol 2 but it's also reprinted in Batman:The Dynamic Duo Archives Vol. 2 and Showcase Presents Batman Vol. 1.
kalorama
08-15-2008, 12:07 PM
I'm surprised nobody has mentioned Englehart's "Malay Penguin" story. If you only buy trade collections, you're in luck: I don't think the Englehart run has ever been out of print, particularly in the recent "Batman: Strange Apparitions" comic.
The great part about the Malay Penguin story was how it showed that, despite the Penguin's funny looks, he's not a funny little man: he's a very skilled criminal mastermind and planner, but one that, like the Riddler, plays "fair," according to certain rules that define his capers. The Penguin has a hammy theatricality as well, and an obsession with birds.
One of the best depictions of the character ever.
Vigilante Man
03-27-2010, 05:47 PM
I really liked Englehart's take on the Penguin myself. What was Ostrander's "Penguin Triumphant" like?
byron lomax
03-27-2010, 06:36 PM
What was Ostrander's "Penguin Triumphant" like?
It's OK. The plot will keep you interested though the ending isn't great.
Keehar
03-27-2010, 06:49 PM
I thought Penguin Triumphant was pretty enjoyable too though its been ages since I've read it. There was a couple of good Grant/Aparo/Breyfogle Penguin stories in the late 80s early 90s too - "The Penguin Affair" and the two-part "Snow and Ice" which was a "Death of the Penguin" story that ran in Detective Comics.
http://www.coverbrowser.com/image/detective-comics/610-20.jpg
There was also that one episode from the Animated Series "Birds of a Feather" which manages to make you feel bad for old Oswald.
That was a great one. Alan Grant wrote the Penguin superbly. Should also check out his story in Secret Origins special:
http://s.ecrater.com/stores/105125/49e180d4b9aa7_105125n.jpg
FanboyStranger
03-27-2010, 08:26 PM
I'll second that Jason Aaron Penguin story from Joker's Asylum. The best Penguin story in a long time.
Hatut Zeraze
03-28-2010, 12:30 PM
I wouldn't exactly consider this a Penguin story, but the Suicide Squad story in which they invaded Russia to free up Nemesis, they recruited the Penguin. He ended up putting together most of the plan (which, of course didn't work out because, well, it was a Suicide Squad comic book).
GamerSlyRatchet
03-28-2010, 05:57 PM
I've never felt that Penguin held his own as a Batman villain. He's a cookie-cutter Dick Tracy villain through and through -- mob boss with a defining physical deformity from which he gets his name. There really isn't much more to the guy beyond the gimmicky umbrellas. I supposed Paul Dini has written him best in his current Detective Comics run, but I wouldn't expect him in a Nolan film anytime soon. Anything Tim Burton added to the guy in Batman Returns was strictly his own invention, not based on the comics.
THANK YOU!
I'm glad I'm not the only one who is not impressed by the Penguin. The fact that my preferred versions of the character include the 60's TV show one, the one in The Batman, and the Tim Burton one proves this.
Captain Jim
03-28-2010, 07:15 PM
I've never been particularly impressed by the Penguin either. In the 1940's and early 1950's, he was a character who used trick umbrellas to commit bird-inspired crimes (yawn). He actually dropped out of the comics for several years before being brought back during the New Look period and later for the TV show. In the early 1970's, DC successfully revamped the Joker and brought back the long-missing Two-Face, but their repeated attempts to update the Penguin were less than successful, in my eyes. His current position as a gang boss is probably the best he's been portrayed, but even that's not overly exciting IMO.
OverMaster
03-29-2010, 07:41 AM
Is "The Killing Peck" that Secret Origins Penguin story? Wonder why it's in a Two-Face/ Riddler book.
It's because they had to. The special is set around a framing device involving all three stories (Penguin's, Riddler's and Two-Face's), and leaving the Penguin one out would have ruined the narrative flow out.
If you can catch The Batman & Robin Adventures # 4 by Ty Templeton and Rick Burchett, check it out. It's a great underrated Penguin story with a nice little sentimental ending.
Keehar
03-29-2010, 08:20 AM
If you can catch The Batman & Robin Adventures # 4 by Ty Templeton and Rick Burchett, check it out. It's a great underrated Penguin story with a nice little sentimental ending.
That was very good.
JerryvonKramer
05-22-2010, 06:00 PM
Just came across this tonight from the 1968 Filmation animated series:
In and Out Again Penguin (http://www.youtube.com/watch?v=t52QgJO50Vs)
Obviously, the execution there is somewhat truncated but Penguin's plan is actually pretty ingenious:
- Break out of jail
- Do a bat-themed robbery leaving, for example, a batarang at the scene of the crime
- Break back into jail
Classic frame up. I think a writer with some real imagination could make that story work.
Vigilante Man
05-22-2010, 10:28 PM
"Penguin Triumphant" is a must read for Penguin fans. "The Malay Penguin" is also great and it's probably my favorite Penguin story. Doug Moench did a great Penguin story in the eighties. Part one of the story is collected in the Batman in the eighties TPB. Penguin is one of Batman's most clever foes and he should get more respect.
WilliamMcGuire
05-23-2010, 12:40 AM
THANK YOU!
I'm glad I'm not the only one who is not impressed by the Penguin. The fact that my preferred versions of the character include the 60's TV show one, the one in The Batman, and the Tim Burton one proves this.
I think the "I don't like The Penguin" sentiment is bunk. Furthermore, I feel like the current incarnation of Oswald (the Sidney Greenstreet) sort of misses the point of the guy.
The Penguin is patently ridiculous in every area except one-- he can (and will) kill you. Here is a character so obsessed with his own image that he wears Bertie Wooster suits with a size 45 waist; and delivers mixed metaphors through squawks. He uses trick umbrellas. His every choice is designed to show the observer that he is cultured, literate, and tasteful-- and yet he is a profane mess. In this sense he is completely ridiculous.
He would be completely so-- except that he's intelligent, motivated, and vicious. The idea of a false image designed to impress (which fails), which masks sadism is an interesting counterpoint to Batman who projects an image of sadism and fear to save people. He's been mishandled because he doesn't work in the same way the other bad guys do (for whom a revamp is simply a restatement of their initial fetish and a newfound desire to kill). The best Penguin stories are more like new games of chess. They require the writer to work more closely in the mystery genre, where the end of a story is the solution of a puzzle, rather than the way contemporary Batman stories work-- where the climax is always a fistfight.
He's a guy forcing the world to be a certain way (just like most of Batman's bad guys) and willing to kill everyone to make it happen. His (and The Riddler's) exile from their traditional roles is more an indictment of the current Batman teams, than of the character itself.
Crimson Knightman
05-23-2010, 09:21 AM
I've never felt that Penguin held his own as a Batman villain.
Me neither.
To me, The Penguin has always come across more as a minor annoyance, a mere pest as oppose to a worthy adversary for Batman. Even when the writers decided to make the Penguin into a mob boss, I never bought into the idea that anyone would respect nor fear him enough to consider him a force to be reckoned with which is a necessity for a mafioso don.
I can see how the presence of the Joker or Two-Face or Ra's Al Ghul or even the Black Mask would conjure up enough fear to put Batman and his cohorts on red alert but the Penguin? Not so much. A short, pudgy guy that waddles equipped with trick umbrellas doesn't fit the bill of a major league antagonist for Batman.
Keehar
05-23-2010, 10:06 AM
The Penguin can very much hold his own against Batman. And has proven so many times.
RubberLotus
05-23-2010, 10:53 AM
Personally, I don't think that Penguin works as an out-and-out mafia don. He's more the guy you go to for supplies/funds/hideouts/information, all for a price, of course.
He never personally involves himself with capers. Why should he? The Iceberg Lounge's overpriced T-shirts and casino haul in all the cash he'll ever need.
Heck, I think that the fact he's even dipping his nose in crime AT ALL is exactly why he's part of Batman's rogues gallery: He's obsessed. Obsessed to a point where it interferes with his ability to live an ordinary life. Why isn't he in Arkham? Because he's found a way to channel that obsession into a profession that modern society finds acceptable.
What is his obsession? Superiority. Proving himself the Top Bird of Gotham one way or another. He's certainly near the top of the ladder, as far as things go - not exactly Lex Luthor, but almost every hood in Gotham has to encounter him, his services, or his wares at one point or another.
But he's not at the top. Not by a long-shot. A ton of people are above him in prestige, wealth, etc., but only one man goes so far as to openly flaunt his power over him Every. Single. Week., or so Oswald thinks: The Batman.
Oswald's current position as a broker of all trades in Gotham, IMO, is the closest he can come to having more power than Batman. It's not out-and-out superiority, but instead a sort of bizarre No-Man's-Land Stalemate - Batman tolerates him, and perhaps even needs Oswald and the nuggets of underworld information he produces.
In my honest opinion, The Penguin doesn't need to rub shoulders with the underworld as much as he does in the current Bat-Books. In Penguin Triumphant, he invented a gadget that pretty much let him take control of the stock market. That alone could have made him a millionaire. So why does he keep playing the "honest businessman" instead of retiring in luxury? Because in his mind, doing so would be admitting that the Batman won. That he no longer has the stamina to keep himself in the race.
In a way, The Penguin is perhaps even more conceited and obsessed with Batman than The Joker is.
And now I've just wasted ten minutes of my life typing an essay about a short fat little man in a top hat and tails that uses weaponized umbrellas. Damn you, Cobblepot! :tongue:
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