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
SHOWCASE '94 #7:
The Penguin has taken Sarah Essen Gordon hostage and Commissioner Gordon must engage the villain in a battle of wits to free his wife, while the Penguin seeks to prove that the Batman who is currently at large in Gotham City is not the original.
DETECTIVE COMICS #683-684:
A man who calls himself "the Actuary" wins $100K at the Penguin's casino. He has a sytem that can be applied to any set of statistics. He used to work in insurance, but got bored. Rather than having him killed, Peguin engages him to use his system to thwart the Batman. Knowing that Batman eschews being seen in public, the Actuary's first plan is to rob the box office of a hockey game, the henchman then changing clothes and staying for the rest of the game. This scheme doesn't work, but Penguin gives the Actuary a second chance. This time he plans a job in the daylight.
The Gotham City Flower Show is to be held in the new Riverside Convention Center. The Penguin arranges for a penguin sculpture made of flowers to be brought in in a sort of "Trojan penguin" scheme. But Batman gets word of this, too, and closes the atrium roof to simulate nighttime. He tracks the henchmen back to the Penguin's casino, but Penguin frames the Actuary, claims he's making a citizen's arrest, and gets off scot free.
BATMAN #548-549:
In 1995 I dropped all of the "Bat-titles" except one, Batman, for reasons expounded upon in the "Joker" thread. I will say that, if Steve Englehart & Marshall Rogers were the "definitive" Batman team of the '70s, then Doug Moench & Kelley Jones were of the '90s. In this classic tale, the Penguin comes out of retirement and commits requisite bird crimes. He doesn't leave enough evidence for Batman to score a conviction, but all his crimes were against the "Black Mask" society. after that, he goes back into retirement. With this post, I bring this discussion to a close (or at least put it on indefinite hiatus).
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