The Penguin first appeared in two consecutive issues of Detective Comics.
DETECTIVE COMICS #58 - "The Penguin"
Bruce Wayne and Dick Grayson are visiting an art exhibition when they take note of an odd little man who resembles a penguin. Suddenly, one of the guards announces the two small Watteau paintings have been cut from their frames. All of the meseum's patrons are searched, but the paintings are not found. Later, the odd little man goes to a hotel of one of the biggest racketeers in town, known only as the "Boss," introduces himself as the Penguin and produces the stolen paintings from inside the handle of his umbrella. The Boss lets him join the gang, and soon Penguin is directing all of the mobs activities and planning their jobs.
The next day, Bruce Wayne is at the Stahl Auctioneering House and sees the same odd little man he saw at the museum the day before. Suddenly the lights go ouot, and when they come on again, the Great Columbia Diamond is missing! Later, at the Boss' headquarters, Penguin insists on his share of the money for the robberies he has planned, but the Boss says, "You're gettin' too big for your shoes -- I've gotta teach ya a lesson so's you won't step into mine!" The Penguin replies, "This was bound to occur sooner or later -- might as well get it over with now." He shoots Boss with his umbrella and takes over the mob.
Later, in a waterfront dive, a disguised Batman overhears two of the Penguin's men planning to hit the Stahl Auctioneering House again. Batman is there waiting for them, and manages to overcome them both before the Penguin himself arrives. When the Batman moves to apprehend him, the Penguin subdueshim with knock-out gas fired from guess where? the Penguin then frees him men, steals a jade idol from the vault, and trips the alarm. When the police arrive, they find the Batman just coming to his senses. they take the dazed Batman to a luxurious mansion as a "formality," explaining, "We want you to tell Mr. Boniface what happened to his idol." Just then, in walks Boniface himself: the Penguin!
Boniface alleges that the Batman has been threatening him for weeks, demanding protection money and saying that he himself so well-known that no one would believe Boniface if he spoke up and complained. Boniface presses formal charges, and the police have no choice but to haul him off to the station in a paddy wagon. On the way, however, the Pernguin's men t-bone the police van. The cops are knocked unconscious and the Batman is dazed. Penguin's men haul himback to the mansion, where Penguin explains the frame-up. First of all, his idol was insured, so he'd collect for it being "stolen" anyway. Now that the Batman has "escaped" police custody, if he stays there he's guilty, but if he escapes he runs the risk of being shot by the police.
They tie him up, but he activates his wireless radio (which is now in his boot rather than his belt buckle where it has been all along) and taps out a message in Morse code to Robin that he's being held in the Boniface Mansion on Lincoln Ave. Robin arrives and a fight ensures, but the Penguin gets the drop on them with his umbrella and calls the police. Batman decides to beat a strategic retreat, but for the next several nights a blind man and a street urchin are seen standing outside the Penguin's mansion. They trail him to the gang's next job, in the bowery where a "humble flop house" stands next to the "tall stately building" next door which houses the diamond exchange.
B&R burst in just as the crooks have broken into the vault, but the Pengiun shoots acid at them from his umbrella. He misses (and hits one of his own men in the process), but escapes in the confusion. Batman chases him to the elevated train station nearby. Their scuffle throws them onto the tracks on an oncoming train. Penguin manages to leap aboard the express train on the next track, but Batman is trapped under the local until it departs. Batman is able to clear his name, but the Penguin has gotten away. "Somehow," he speculates, "I feel we'll meet him again!"
DETECTIVE COMICS #59 - "The King of the Jungle"
"Again" comes in the very next issue. Batman knows the Penguin's name and address, so the Penguin switched to a frieght train heading toward the midwest. Inside the boxcar he meets Lefty Larry and Mike the Tramp. He gets their attention by shooting the hat off Mike's head (with his umbrella, 'natch), and outlines his new plan. Mike and Lefty spread to word to all the tramps with criminal records to gather in the hobo jungle (the "jungle" of the title) outside Boswick. His plan to to turn each of the hobos in for their respective rewards, break them out of jail, them split the profits. Coincidentally, Bruce Wayne and Dick Grayson happen to be on vacation and are on a train passing through Boswick when Dick spots the Penguin.
That night, the Penguin turns one of the bums in for a $15K reward. Later, "a pudgy, smartly-gloved hand drops a tiny pellet into the jail's ventilating system." The resultant gas knocks out the guards and the hobos free Mike. Back at the hobo jungle, Batman and Robin go on the offensive, but they, too , are overcome by knockout gas fired from... Aw, you guessed! They come to their senses with their feet tied together, hanging upsidedown from hooks in a box car. That's not much of a "deathtrap," so they quickly free themselves and return to Gotham City. Once there, they consult Batman's "personal rogues' gallery" and learn that Penguin's man "Bignose" is wanted in Memphis, Mike the Tramp in Arkansas, and Lefty in Texas.
Days later, the Penguin runs his scam in Memphis, and Batman deduces that Arkansas will be next. They fly there in the batplane in time to catch Penguin in the act of his next job. He fires teargas, from his boutonniere this time (ha! fooled ya!), but the handle of him umbrella is weighted with lead. Batman and robin pursue him to the Mississippi River where he and his men board a riverboat. A fight ensues. Batman and Robin are knocked overboard, but ride the paddlewheel back on deck. The Penguin attacks Batman with his unbrella-sword, but realizes he is outmatched, jumps overboard and does not resurface.
BATMAN: Well -- the end of the case -- and certainly the end of the Penguin, eh, Robin?
ROBIN: I dunno! I've got a funny feeling --
BILL FINGER: Only the silent waters of the Mississippi know the answer of the Penguin's end, and they won't tell!
Replies
I've heard that the Penguin was inspired by either the Kool Cigarettes Willie the Penguin or the Dick Tracy villain Broadway Bates (1932).
In fact in 2012, they made Bates and the Penguin brothers!
BATMAN #11 - "Four Birds of a Feather!"
The Penguin gets himself three new partners: Joe Crow, Buzzard Benny and the Canary. (Crow has green skin for some unexplained reason.) They all decide to head to Florida for the winter and open a casino called "The Bird House" in Miami Their claim to fame is that they are an honest gambling house with glass tables. (The glass tables are supposed to prove there's nothing hinky going on, but they're rigged, anyway.) They do let their some of their patrons win big, but then they rob them after they leave.
Coincidentally, Bruce Wayne and Dick Grayson are on vacation in Miami, their two-man yacht anchored just of Miami's shore. Suddenly, they hear a woman scream for help. They look out the portal to see a woman being attacked by a giant squid. Despite the fact they are both already wearing bathing suit, Bruce takes the time to put on his full Batman costume, including cape, before leaping in to save her. Despite the delay, he brings her to safety and guess who it Is? That's right, the Canary! Later she tells the Penguin that his "old friend" is there in Florida.
the cab drivers empoyed by The Bird House circle the city looking for suitable marks. One of them picks up Bruce Wayne and gives him a ride to the nightclub/casino. There he sees the Caneray singing an stage and realizes she is the woman he saved that afternoon. He wins big, and when he sees Buzzard Benny and Joe Crow he figures something's up, so he calls Dick to be standing by. Sure enough, the Penguin's men attack, but they get away.
They next day is a big boat race. the Bird House has an entry, but they are betting against themselves and order their driver to throw the race. But Batman takes the driver's place and a chase along the Venitian Islands ensures, with the Penguin and his cohorts drive a car on land while the Batman follws by boat pulling Robin along on a surfboard. Robin has an accident, however, and is captured by the criminals. Batman corners Buzzard Benny and asks where Robin is being held. Benny tells him, but Canary warns him that its a trap. Benny fires two shots at Batman point blank. Both of the bullets hit, but he covers himself with his cape and pretend that he is all right.
A storn is blowing in. By the time Batman recues Robin from the Penguin and Joe Crow, he is almost ready to collapse. Robin tries to take him to a hospital, but by that time the storm has developed into a full blown hurricane. Having no other choice, he lashes them both to a tree to ride it out through the night. The next morning, the hurricane has blown over and the Canary finds them on the beach. She drives them to the hospital, but the doctors are too busy to help Batman. "Once I was a doctor's assistant!" says the Canary. "Perhaps I can pull him through. Are you willing to let me operate on your friend?" she asks Robin. He agrees.
"Instruments are borroed, and in a room as white as death, a night club singer's manicured fingers toil to give the Batman back his life!" She removes the bullets, and Robin goes to apprehend the other three "birds" by himself. He turns Joe and Benny over to the police, but takes the Penguin to the Batman, whose "physically perfect body" has "rallied," so that he might have the pleasure of taking the Penguin in himself. that turns out to be a mistake because the Penguin snags a passing truck with the handle of his umbrella, tosses out the driver and escapes. The Canary, however, decides to give up her life of crime and become a Red Cross nurse, following in the footsteps of "another woman [who] had a brid's name... Florence Nightengale!"
DETECTIVE COMICS #67 - "Crime's Early Bird"
The Penguin (a.k.a. "Mr. Boniface"), opens The Golded Cage Bird Shoppe as "I.Waddle." He sells a "parrot" (cockatoo, actually) to Mr. Gemly, the wealthy jewel collector. Warning Gemly that the bird is suscepible to colds, he advises him to call at the first sign of one, The he puts sneezing powder in the bird's feed. Gemly says the combination to his wall safe aloud as he opens it, and the bird learns it. then Gemly feeds the bird, it starts to sneeze and he calls Waddle. When the Penguin gets there, the bird repeats the combination and Gemly pretends not to know what it is. Then the Penguin sprays the germ of psittacosis, or "parrot fever" (which is deadly to humans as well) from his umbrella, killing both Gemly and the bird as well. Then he opens the safe, sends the jewels to his shop via homing pigeon, and calls the authorities. When the coronor diagnoses parrot feaver, Waddle is free to go.
Reading of the account in the paper, Bruce and Dick become suspicious, head over to the pet shop and see the Penguin coming out. They follow him to a jewelry store where he asks to see some expensive diamonds. but then leaves without buying them. Suddenly, two jackdaws fly into the jewelry store and carry the diamonds away. From an alley nearby, the Penguin looses a falcon which kills the jackdaws, carrying one in each claw. (The jackdaws don't drop the diamonds because their feets were coated with rubber cements.) Batman and Robin follw the Penguin back to his shop, but the Penguin squirts "liquid fire" from his umbrella and rides an ostrich to safety. B&R stay behind to save the Penguins henchmen.
Robin finds the stolen loot in the bill of a pelican. Then Batman baits a trap with Bruce Wayne's jewels and lets the Penguin's men "escape." B&R also save the Penguin's homing pigeons, release them, and follow them in the Batplane to the Penguin's penthouse. Later, his men have delivered Bruce Wayne's ungarded jewel box. Penguin opens it to find that its full of bats! B&R burst in, and the Penguin sprays them with sneezing powder. (In retrospect, it's lucky he didn't spry them with "the germ of psittacosis.") He ties them up, then leaves his pet penguin to "keep them company." Then he goes into his lab to put the finishing touches on a deadly new gas he's been working on so he can try it out on them. While he's away, the Batman "convinces" the penguin to bring him a lighter which he uses to burn through the ropes binding his hands.
The Penguin slides down a wire from the penhouse to a nearby bell tower. B&R follow. The bats released earlier swarm around the Penguin's head, but he whistles for a pair of trained eagles which keep B&R busy while he escapes via umbrella.
BATMAN #14 - "Bargains in Banditry!"
"Cutting prices seems to be the trends," observes the Penguin. "Why shouldn't I adopt the latest methods of attracting victims -- I mean, customers?" He then sets about printing up price lists of crimes he will plans for others to pull. He will sell the plans, then also reap a percentage of the profits. His first customers are Torchy Blaize and Hairless Harry Hix. He sells them plans for a bank robbery, which goes off without a hitch. then he shows up to collect his share of the haul... which is 100%. He shoots them both with poisoned darts fired from his umbrella, killing them both.
Batman & Robin are keeping Grand Boulevard, where the big jewelry stores are located, under surveillance. Their persistence pays off as they observe the Penguin's most recent client, Slippery Elmer and his gang, robbing one of the shops. They capture the gang, but Slippery elmer himself escapes. B&R track him back to their hideout, and intercede just as the Penguin is about to kill Elmer. They manage to save his life and capture him, but the Penguin escapes.
Batman's next ploy is to masquerade as "Bad News" Brewster and set himself up in competition with the Penguin. Brewster is selling "accurate models of banks, jewelry stores, meuseums -- showing burglar alarms, cuards' posts, etc. -- For Sale Cheap!" Brewster's first client is Glitter Gleason, who buys a scale model of the Persian Room of the Cosmopolitan Museum. The room is rigged as a trap, however, and Gleason and his men fall into it. But the Penguin has taken the bait. He sends a telegram to Brewster inviting him to a certain address, but it is Batman and Robin who arrive.
Upon entering the room, they step onto a giant umbrella, which closes arounf them and gasses them into unconsciousness. When they awaken, Robin is tied, and Batman has a target around his head. Penguin proceeds to throw poisoned darts at his head, but Robin usets the umbrella stand and begins firing them at random. One sprays acid, another blinds the Penguin with green paint. Batman uses the spilled acid to free himself from his bonds, they capture the Penguin and turn him over to the police. Penguin vows revenge, but later Bruce and dick hear a radio broadcast the the Penguin has been sentenced to death for the murders of Hairless Harry Hix and Torchy Blaize.
BATMAN #17 - "The Penguin Goes A-Hunting!"
Penguin has escaped from jail. Curiousity leads him to Warden Keyes' lecure on "Today's Greatest Criminals and their Foes." Bruce Wayne and dick Grayson are also in attendance. About the Penguin, the Warden says, "Without his trick unbrellas, he'd be just another third-rate chisler with delusions of grandeur!" Asking this question in an auditorium filled with police, guards, the Warden and other people who might recognize his was perhaps not the wisest move, and indeed, he is recognized. He escapes however, and takes the warden's criticism to heart, stealing fishing rods, rifles, polo mallets, etc. from a sporting goods store.
His first crime is to hook a stack of valuable bonds from Mr. Throckmorton, a stockbroker. For his second crime, he crashes the birthday party of millionaire Tyrus Wolff's young son. As a gift, he has delivered a large rubber wolf that could be used as a flaot toy. then he shoots it with a hunting rifle, realeasing knockout gas and loots the unconscious party guests at will. His third crime is to dress as a jocky and ride a hourse into a sportsmans' show and steal all the trophies. It is during the commission of this last crime that Batman captures him... using lawn umbrellas!
BATMAN #21 - "The Three Eccentrics!"
In a dive bar, a safe-cracker named Sam Chizzell and a second-story man called "Spider" grumble of the headline of a newspaper Chizzell found in the gutter: Tac Returns Show Three Eccentics to be Richest People in Nation!!" Ebenezer Flint distrusts banks and keeps all his money in a wall safe in his home; Gladys Puffe plans to leave her entire estate to her pet Pekengese; philanthropist John White opens his hilltop castle to the homeless. Penguin recruits them to exploit all three millionaires.
1st crime: Penguin manipulates Ebenezer Flint into opening his safe whil Penguin uses his umbrella movie camera with telephoto lens to record the combination from outside the window.
2nd crime: Penguin, Chizzel and Spider kidnap Gladys Puffe's dog for ransom. B&R manage to thwart this one, but Batman gets tossed into a patch of quicksand while Robin gets left behind. Batman manages to free himself with the help of one of Penguin's discarded umbrellas.
3rd crime: Penguin, Chizzel and Spider break into John white's castle only to fin B&R waiting for them. Chizzell thinks Batman is a ghost, and Robin is inside a suit of armor. they round up the crooks easliy enough.
Later it is revealed that the newspaper chizzell found in the gutter was from 1941, but it is not explanied why it was in the gutter after three years or how they could have all mistaken it for a current paper. As it happens, Bruce Wayne reveals that John White had died over a year ago. For some reason, this is supposed to be significant. Dick Grayson says, "Hmmm... must be a moral somewhere!" don't worry, Dick. If there is, I can't figure it out, either.
DETECTIVE COMICS #87 - "The Man of a Thousand Umbrellas!"
The Penguin has escape from the penitentiary but has been lying low. Bruce and dick decide to flush him out by use of a horse-drawn unbrella repair cart. Surprisingly, this lame ploy actually works. Nearby, the Penguin has damanged one of his umbrellas during a jewel heist and sends a note signed "Mr. Feather" directing them to his house to make several repairs. When they discover that Mr. Feather is the Penguin, they sabotage his umbrellas (but we aren't supposed to know about that until later in the story). Returning later as Batman & Robin, they capture his man but the Penguin escapes. Going forward, Bruce and Dick resolve to take a close look at anyone carrying an umbrella on a sunny day. Suddenly, everyone is carrying an umbrella, and they trace them to the umbrella shop of P.N. Quinn who is giving them away for free.
Deathtrap: They are caught in a cage made of umbrella stays but manage to escape just before they are electrocuted. the last thing they do is to open all of the umbrellas in the shop. Then they track Penguin to his latest job, which is when he realizes all of the umbrellas he has with him have been tampered with. They chase him back to his shop, when he is caught in a tangle of opened umbrellas.
BATMAN #25 - "Knights of Knavery"
As the story opens, Batman and Robin apprehend the Penguin while he's trying to steal the Van Landorpf emerald. He is thrown into a cell with the Joker, and they decide to compete for exclusive control of the Gotham City underworld to be determined by which one steals the emerald. By the next page, they have broken out of prison. Mrs. Van Landorpfis to appear at the Ritz Fashion Show as "America's Best-Tailored Woman." Batman approaches her about placing a notice in the society column that she will be wearing the emerald to the event. The whole the is a ruse, such an obvious trap they don't expect the Penguin and the riddler to fall for it. Instead, they expect the titular "Knights of Knavery" will stike the "unguarded" safe at the Van Landorpf home.
When Penguin reads the notice that Mrs. Van Landorpf is to wear court emeralds with a tailored suit he realizes that that simply isn't done, but he expects the Joker to hit the fashion show. To his surprise, however, the Joker shows up at the Van Landorpf home as well, and to the surprise of both of them, the Batman and Robin are waiting. All of the Joker's and the Penguin's men are captured, but the Joker and the Penguin themselves get away, and decide to team-uip. They soon embark on a successful crime spree. During one of the jobs (which Joker planned but the Penguin pulled off), B&R are captured. To make a long story short, Batman stalls them long enough to escape and he and Robin captures them both. (They are put in separate cells this time.)
BATMAN #27 - "The Penguin's Apprentice!"
The Penguin takes on apprentice due to writer's fiat. they start small by stealing a handkerchief from a vagabond and a feather from a lady's cap, but the boy's heart isn't in it. He wants to be a writer instead. The Penguin sends him off to study his notes, but when he checks in on him an hour later he finds the boy writing the Penguin's biography. Having a biography written about him appeals to the Penguin, so he shops it around to a publisher. Bruce Wayne happens to be there, too, because of coincidence he "has a financial finger in many a pudding." The publisher turns the manuscript down because such a book "would appeal largely to the underworld and give them too many ideas." He wouldn't publish such a book "uless it were properly slanted by an authority on crime."
This give Penguin the idea to self-publish and market it to the underworld as a "how-to" book on crime. Before leaving the publisher's office, the Penguin overhears news of a paper delivery comin in over Route 66, but on his way out of the office he dropas a random page of the manuscript (p.165), which Bruce Wayne picks up. It is only after reading that page, which describes something only the Penguin and the Batman could know, that the "World's Greatest Detective" figures out the funny little man was the Penguin himself. Suspecting that the Penguin intends to hijack the paper shipment, Batman and Robin follow along in the Batplane. They try to attempt the theft but are overwhelmed and captured.
The Penguin plans to take his book to Snipe the counterfeiter to be printed, but he leaves Batman behind to write an endorsement for the bookjacket by gunpoint. Batman uses a rubberband to fire the fountain pen's rubber ink sac at the guard and overcomes him. The boy provides a clue as to where Snipe's printing press is hidden. It is across from the clock tower of the Gotham Trust Building. The time is 9:36. Penguin jumps out of the window using his umbrella, but he drops it after landing on the big hand of the clock. Batman swings over and lands on the little hand. Now it is just a matter of minutes until the hands come together.
Batman is convinced of the boy's innocence and doesn't turn him in. Later, the boy rewrites the biography with the slant "crime does not pay" and Batman ends up endorsing it after all. Advance notices indicate that the book will probably be a best-seller.
DETECTIVE COMICS #99 - "The Temporary Murders!"
This time, Penguin is using cryogenics as a scam. He has kidnapped and "frozen" three victims, holding them for $50,000 ransom each. The story correctly points out that problem with cryogenivs is not freezing people, but thawing them out. He's faking the whole process, though. He has actually created wax figues of his victims and frozen those; the people themselves are safe.
Deathtrap: He does, however, try to actually kill B&R by freezing them
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