Penguin established himself as a master criminal in Gotham City, and became an arch-foe of Batman. They clashed many times over the years with Batman always coming out on top, usually by exploiting Penguin's vanity.

(Batman I #169) - Penguin was released from prison, and wracked his mind for a scheme worthy of his criminal genius. He decided that he'd bait Batman into coming up with a crime for him, so he gave away weaponized umbrellas to customers of a jewelry store and a bank, and although they caused chaos he didn't rob either target. He then released a giant umbrella that blotted out the sun over Gotham Square. Batman and Robin paid him a visit at his umbrella shop, and he said he merely sold umbrellas, so he couldn't be responsible for what happened to them after they left his shop. He also switched his monocle to his left eye to mess with the Dynamic Duo, who rightfully suspected he was up to something. Penguin later released a multicolored glowing umbrella, and Batman thought it was a clue indicating that Penguin was going to rob the jeweled meteorite from the museum. Batman figured that the easiest way to avoid security would be to open up a hole in the museum's roof and use an extendable umbrella to steal the meteorite. When they'd visited Penguin he'd placed microphone transistors on them, and went out with his gang to commit the crime Batman came up with. He used a magnet to temporarily immobilize Batman and Robin, but they freed themselves as Penguin zoomed off with the meteor on a jet-umbrella. Batman and Robin took his goons jet-umbrellas, and ran him down. Penguin was back behind bars, but felt he'd won a minor victory when Batman still hadn't figured out his monocle angle, and would be taking it home to analyze it.

(Batman I #190) - Penguin thought scientific crimefighting devices called for a response for today's criminal. He proclaimed his genius, and showed his henchmen his new inventions; air-conditioned suits to beat the Gotham heatwave, and energy pills to keep them at peak efficiency. He couldn't wait to show off his innovations to the Dynamic Duo, and he got his wish when the heroes interrupted his robbery of the International Gold corporation. Batman and Robin's boots stuck to the floor, allowing Penguin's goons to hammer away at them, and Penguin claimed he was using a gravity ray. Batman figured out he'd put a magnet under the floor, and they'd stepped in iron fillings, so he urged Robin to remove his boots. The thugs were wearing Penguin's fist fender-off devices, pumping air from their costumes to keep knocking away Batman and Robin's punches until the heroes fought more unpredictably, hitting the thugs before they could activate their devices. Penguin escaped with the gold on his jet-umbrella, and complained that his plans were brilliant but his henchmen were fools. With the cheering of his Penguin-Robot, who loudly talked up his genius Penguin created a series of remote-controlled Robotrella, robotic umbrellas, and the Dynamic Duo witnessed his umbrellas pull off a jewelry heist. They created Batrellas to follow Penguins Robotrellas after they pulled their next job, and brought Alfred along. After a wild battle with the Robotrellas, the heroes were captured in a net-umbrella, and dragged away by Penguin's robot double. They escaped the robot, but Alfred staid behind, and watched the Robotrella loot sink into a hole in the ground. He jumped in, and found Penguin's new underground hideout, knocking him out with a blow from his own umbrella. Penguin grumbled about being in prison until he learned his cellmates name was Brolly, English slang for umbrella. He said Brolly would be an invaluable ally in his next prison escape.

(Batman I #191) - Ira Radon, expert on radiation and crime, doused Batman and his gear with radiation. Radon informed Batman that his body was now radioactive, and unless he auctioned off all his crimefighting career and quit, Radon would boost the radiation in his system and kill him. Batman called a press conference announcing his retirement and the auction, and when Penguin got the news in jail he was disappointed that he'd never again match wits against his nemesis. Batman was only playing along with Radon in order to capture him, and after removing the radiation from his system he announced his comeback.

(Detective Comics I #472) - Bruce Wayne went for treatment at Graytowers, a clinic that catered to the rich and powerful and didn’t ask many questions. Graytowers was actually run by Professor Hugo Strange under the alias of Dr. Todhunter. He turned his clients into Monster Men, forcing them to obey his whims in exchange for receiving a temporary antidote. Each of his patients was ordered to bring one new wealthy Gothamite to his clinic. Bruce confronted him as Batman, but a green mamba hidden in Strange’s office bit him, rendering him comatose. When Strange revived him Batman was horrified to realize Strange had removed his mask and knew he was Bruce Wayne. Strange’;s Monster Men kidnapped Alfred and Strange posed as Bruce, selling off millions of Wayne Enterprise’s stocks. Strange arranged an auction for Batman’s secret identity, with a $10,000 buy-in. Joker, Penguin and Boss Thorne responded, and Strange planned to hold the auction the next night. Strange intended to kill Bruce Wayne before the auction, knowing that keeping him alive was too dangerous to his plans. Boss Thorne’s men shot the Monster Men that were escorting Strange with tranquilizer darts, and brought him to city hall, demanding to know Batman’s identity and saying he didn’t intend on paying for it. Robin broke into Graytowers, fought off the Monster Men, and freed Bruce and Alfred. Thorne’s men savagely beat Strange, but he’d made up his mind not to reveal Batman’s secret. He said he’d earned that knowledge and would never give it away because Batman was the one man he saw as a worthy foe. Strange said Thorne would have to defeat Batman himself, as he had, to learn his identity. Thorne did not understand Strange’s loyalty to his nemesis, and his men beat Strange until he was seemingly dead.

 (Detective Comics I #473) - Penguin and Joker arrived at the auction, and was angered that no one else was there. The Reed Gallery was exhibiting the Malay Penguin and Batman and Robin visited Mr. Reed, warning him that the Penguin would surely target his art show. Reed showed off his security system, but Batman warned him that Penguin loved a challenge. On patrol Batman and Robin spotted the Penguin, and tried to apprehend him, but he flew away with his buzz umbrella and warned them not to tangle with banks. The Penguin bankrolled a theatre company to play next door to the Reed Gallery, whose performance caused the gallery’s security system  motion detector to keep going off. Batman realized that Penguin was drawing attention to the Reed Gallery to divert him from the crime he was actually planning. The Penguin tried to hijack an airplane carrying members of the security exchange and Batman and Robin apprehended him. Penguin congratulated him for figuring out his scheme, and tossed him the Malay Penguin. He’d stolen the art piece weeks ago, and the piece on display at the Reed Gallery was a fake.

(Detective Comics I #474) - Penguin returned to prison and taunted Deadshot Floyd Lawton, saying that while he was in and out of jail as he pleased Deadshot had been rotting away since Batman defeated him years ago. Penguin showed off his monocle, which contained a laser lens he’d use to break out again. Deadshot took Penguin’s words to heart, angered that he’d never gotten a chance for revenge against Batman, and snatched the monocle, activated the laser and freed himself.

(Suicide Squad I #3) - Penguin witnessed the Female Furies’ assault on Belle Reve prison from the relative safety of his cell.

(Batman I #564) - Penguin sold arms to the False Facers gang and stashed a shipment of guns with Father Chris and his church, convincing the father that he was keeping guns off the streets. When the False Facers learned of the arsenal's location they went after the church and Batman convinced Penguin to talk to him. Penguin obliged when Batman threatened to take his generators offline with an electromagnetic pulse. Penguin reminded Batman that law was a construct of civilization, and no longer applied to the No Man's Land. Penguin theorized that Gotham's new civilization could be built on a list of laws that he wrote.

(Batman: Harley Quinn #1) - Penguin refused to sell Joker firearms and supplies for a new criminal operation until Harley Quinn and the Joker’s goons forced his hand.

(Sins of Youth: Batboy and Robin #1) - Penguin noticed Klarion drinking in the Iceberg Lounge, and thinking he was underage, tried to kick him out. Klarion got insulted and de-aged Penguin into a child so that Penguin could serve in his Junior Injustice Society.

(Young Justice: Sins of Youth #2) - Under orders from the Agenda Li’l Pengy and the Junior Injustice Society led coordinated attacks on Gotham, Metropolis and Happy Harbor. They were opposed by Young Justice, the JLA and JSA, but were teleported to the Agenda’s Alaska hq when the heroes turned their attentions there. The heroes defeated the Junior Injustice Society and dismantled the Agenda’s Alaskan operation. In order to be reunited with his familiar Teekl, whom Young Justice had captive, Klarion returned Penguin and all the other de-aged superheroes and supervillains to their proper age.

(Batman: Gotham Knights #6) - Penguin's associate Bentley Stuart hired some of Penguin's goons to scavenge the rubble of a bank vault and steal some papers that incriminated Councilman Waldemar. Penguin didn't like this unauthorized blackmail scheme and sent some of his men to  kill Stuart. Batman questioned Penguin about the Waldemar case, and Penguin explained the situation to him. Batman apprehended Stuart  before Penguin's goons could kill him.

(Batman/Scarface: A Psychodrama #1) - As part of Jeremiah Arkham’s therapy the Ventriloquist was convinced to throw his puppet Scarface into the sea, removing the physical manifestation of his split-personality. The Ventriloquist was released from Arkham, and tried to restart his show-biz ambitions with a ventriloquist act with his new dummy Lola. Penguin attended his first show at Gotham’s Ventriloquist Club, delighted to see his old rival had become a nobody, but Ventriloquist mocked him during his act, infuriating him. Scarface came into Penguin’s possession, and he threw the dummy on the stage during Ventriloquist’s next act, hoping he’d have a nervous breakdown. Ventriloquist’s henchman Rhino convinced him that it was fate that reunited him with Scarface, and Ventriloquist decided to return to a life on crime. Rhino had recorded the audience during Ventriloquist’s acts, just like when he was starting his criminal career, and recorded Penguin working out his next heist, sending expendable men to the Vargas Building as a decoy for Batman while Penguin would join his men hitting the diamond district. Ventriloquist called the GCPD, and while Batman rounded up the men at the Vargas Building Commissioner Gordon and the GCPD foiled the heist in the diamond district and arrested Penguin. Meanwhile Ventriloquist and Rhino burst into Penguin’s Iceberg Lounge, shot a bunch of his men, and stole the money he kept in his vault.

(Flash II #183) - Penguin attended one of the Network’s sales of black-market merchandise.

(JLA #84) - The Burning, who needed fear and chaos to reproduce, unleashed a wave of fear and remorse that washed over the inmates of Arkham Asylum, including Penguin.

(Flash II #210) - Penguin wanted to expand his criminal operations into Keystone City, and to this end he hired Girder and Double Down to act as his enforcers. Flash III and Nightwing defeated the trio and handed them over to the authorities.

(Batgirl I #53) - Batgirl broke up an arms deal, but when the crooks broke out a hi-tech gun she called Batman for backup. Batman sent his new Robin Stephanie Brown her way, and they brought the hi-tech gun to Oracle. Oracle told them the gun was a Masami NK-4, commissioned by the British government and manufactured in an arms lab in Kyoto. Only five were made, and they were all promptly stolen. Penguin was behind the arms deal and had already gotten his hands on the other four. Batgirl and Robin went to confront him, and Robin was overjoyed that Batman had chosen her to be his new partner, saying it was a dream come true. Batgirl and spoiler leaned heavily on Penguin’s men, learning that he was using his underlings with children to have their kids courier the remaining guns. Melanie, the daughter of Penguin henchman Roy brought a backpack to a bar, delivering the gun to a crook named the Gouger. Gouger decided not to pay and Melanie said she’d call the cops because she wouldn’t let him rip off her dad so gouger ordered his men to kill her. Batgirl and Robin showed up in time to protect Melanie and subdue Gouger and his men. After the rest of the NK-4s were recovered Batgirl and Robin confronted Penguin, who was irritated that they’d foiled his business operation but assured them his underlings would serve jail time but he wouldn’t because he had the best lawyers in Gotham. Robin attacked him but Batgirl pulled her off. Robin said she remembered when her father the Cluemaster was arrested for the first time, and she didn’t know who to hate more, her father, the police or the world for letting it happen. Robin wished she knew what it would take to remove people like Penguin from the lives of children.

(Robin II #133, Batgirl I #59) - Penguin moved into Bludhaven and took over Blockbuster’s criminal empire after he was killed by the vigilante Tarantula. At no small expense Penguin had Blockbuster’s corpse stuffed, mounted and put on display at Blockbuster’s former estate, which Penguin now owned. Penguin assembled a criminal army, including Gas Bag, the Trigger Twins and Brutale. Robin and Batgirl moved to Bludhaven, and with the Bludhaven PD looked into who’d moved into Blockbuster’s business. Batgirl and Robin showed up at Blockbuster’s estate only to be confronted by Penguin and his army. Penguin said he specifically came to Bludhaven to get away from the Bat-Family, and was angered Batgirl and Robin hadn’t been driven off by Shrike. Penguin had his criminal army, including the Trigger Twins and Brutale attack the heroes. Batgirl and Robin were outnumbered, but Penguin’s gun-happy goons kept taking each other out with friendly fire. Penguin’s henchman Gas Bag released a knockout gas and when Batgirl and Robin woke they found themselves tied up. Penguin planned to unmask the heroes to expose their identities and then kill them. His henchman Two-Ton asked if he could have the honor of unmasking them, as it would boost his rep. Several other goons started bidding for the honor, so Penguin decided to auction off the unmasking rights, calling in several other gang leaders including Little Willie, Fat Willie and Lavender Bob. Little Willie won the auction, but realizing they had hours to kill before Willie could arrive in Bludhaven Penguin decided to free the heroes and pit Batgirl against Robin, with all his goons placing bets on the winner. Penguin said he didn’t want anyone to feel cheated, so he declared it a fight to the death. Robin hoped that Batgirl could read him and work with him on a plan. Batgirl and Robin fought, taking time to work out some personal issues, especially with how they related to Batman. Batgirl took the dive, and Penguin handed Robin a gun, demanding he finish her off. Robin shot Batgirl, aiming for her shoulder, and when Penguin checked on her she attacked him. Penguin ordered Gas Bag to gas them, but he was recalcitrant, saying Penguin tried to fix the fight. Batgirl and Robin fled Penguin’s estate, taking out both Brutale and the Trigger Twins.

(Batgirl I #60, 62) -Penguin told his adviser Noah Westbrook that he wasn’t worried about Batgirl because he was used to operating under Batman’s nose. Penguin contacted Brain to help him smuggle illegal arms into Bludhaven, even though Penguin never entirely trusted the villain. Brain’s Brotherhood of Evil member Gemini killed customs agent Parker and disguised herself as him to get the shipment cleared. Batgirl investigated Parker’s boathouse, finding his corpse, but was ambushed by the Brotherhood. They beat here severely. During the fight the boat caught on and exploded, and the Brotherhood assured Penguin that Batgirl was dead. Penguin was ready to complete the arms deal, meeting with Society members Lex Luthor, Deathstroke and Calculator. Deathstroke was skeptical that Batgirl was dead, knowing how dangerous she was, and his instincts were correct. Batgirl put the kibosh on the arms deal, defeating the Brotherhood and handing them over to Bludhaven PD, but Penguin had been tipped off that she was slive and flew away from his meeting with the Brotherhood, angered that his plan was a bust but relieved that he wouldn’t be going to jail.

(Batgirl I #63, 64) - When Batgirl foiled Penguin’s arms deal with the Brotherhood of Evil she damaged his standing in The Society. Penguin met with Luthor, Dr. Psycho and Calculator demanding they help him take down Batgirl once and for all. He said Deathstroke was clearly the man for the job, and Deathstroke considered his proposal. Batgirl was the protector of Bludhaven, so Deathstroke started a fire at a business owned by neighborhood couple the Braunsteins. Batgirl investigated and Deathstroke snapped Mrs. Braunstein’s neck in front of her. Deathstroke and Batgirl fought across Bludhaven, and Batgirl could sense he was toying with her. Deathstroke admitted as much, and introduced his daughter Ravager to Batgirl, saying he was saving-the killing blow for her. Ravager was incredibly skilled, but during their fight Batgirl realized how inexperienced she was and temporarily knocked her out. Batgirl saw a lot of herself in Ravager, since both their fathers raised them to be killers. Deathstroke hadn’t interfered in the fight and didn’t retaliate when Batgirl called him pathetic for what he’d done to his daughter. Ravager recovered, promised her father she wouldn’t fail him, and pursued Batgirl, who truly felt for her because it was obvious everything she did was to win her father’s approval. Batgirl fled to an underground tennel system, not wanting any onlookers to get hurt when Ravager caught up to her. Ravager soon found her, with Deathstroke still observing. During the fight Batgirl staid on the defensive and waited for ravager to look to her father for approval and took the opportunity to disarm her. Batgirl used Ravager’s own sword to stab her in the throat, forcing Deathstroke to save his daughter and get her emergency medical treatment. Batgirl knew their fight was far from over, and that Deathstroke would force Ravager to complete her test and go after Batgirl again one day.

(Batgirl I #69) - Nyssa al Ghul had a video conference with Society members Talia al Ghul, Penguin, Deathstroke, Merlyn and Calculator, telling them all was going well with Mr. Freeze’s research to create a machine that could freeze half the world’s oil supplies. She surprised them by revealing she had Batgirl as her captive and told Penguin he should pay her the bounty on Batgirl’s head. She also mocked Deathstroke, who still hoped his daughter Ravager would be the one to take Batgirl out, saying his daughter should set her sights lower and go after third-stringer Flamebird. After the conference Nyssa confided in Batgirl that she hoped to initiate a hostile takeover of the Society alongside Talia.

(Villains United: Infinite Crisis Special #1) - The Society made plans for a worldwide prison break to free every incarcerated supervillain, and one of their targets was Blackgate. Penguin was one of the released inmates, and together with the other freed villains they managed to get past a group of superheroes sent by Oracle to try and quell the breakout.

(Robin II #170) - Penguin was disappointed that his sports bookie Marcel Pincus had been robbed a number of times by the vigilante Violet. He bailed Pincus out of prison and tolfd him the only reason he was alive was because he’d proved he could be a big earner. He demanded that Marcel lure Violet to him, so he could deal with the vigilante himself.

(Robin II #173, 174) - Penguin used Pincus to lay a trap for Robin and Violet at Sea-Fine Seafoods. Spoiler revealed her presence, knocking out Violet, and trying to warn Robin about the trap. He lashed out at her, but their fight was interrupted by Penguin’s agent Sin Fang of the North Korean mafia Robin and company managed to make a getaway. Penguin’s dirty cops Detective Cavallo and Detective Wise. executed Pincus.

Bizarro-Superman wrote and illustrated a comic book titled “Bat-Man” featuring Penguin in Bizarro Comics #1.