Izaya Orihara

{{Infobox (折原 臨也 Orihara Izaya) }} Izaya Orihara (折原 臨也, Orihara Izaya ) is a powerful and skilled underground informant. He usually gives information for his own enjoyment, and claims to love the entire human race, excluding Shizuo Heiwajima. Izaya likes to start fights with him, as seen in episode 25, and then let Shizuo chase him around. He is voiced by Hiroshi Kamiya (Japanese) and Johnny Yong Bosch (English).
 * Box title = {{PAGENAME}}
 * Row 1 title = Age
 * Row 1 info = 23, 24
 * Row 2 title = Job
 * Row 2 info = Informant (Information Broker}
 * Row 3 title = Height
 * Row 3 info = 175cm (5'7.5")
 * Row 4 title = Weight
 * Row 4 info = 58kg (128 lbs)
 * Row 5 title = Blood Type
 * Row 5 info = O
 * Row 6 title = Family
 * Row 6 info = Torakichi (paternal grandfather), Natsu (paternal grandmother), Shirou (father), Kyouko (mother), Mairu and Kururi (younger sisters).
 * Row 7 title = Online name
 * Row 7 info = Kanra (former), Nakura and Chrome (as of volume 08)
 * Row 8 title = Gang
 * Row 8 info = Dollars
 * Row 9 title = Goal
 * Row 9 info = To create a war in Ikebukuro that will "wake up" Celty's sleeping head.
 * Row 10 title = Birthday
 * Row 10 info = May 4 (1979 in the novel) (1985 in the manga) (1990 in the anime)
 * Row 11 title = Dislikes
 * Row 11 info = = Shizuo Heiwajima
 * Row 11 info = = Eyes of dead fish
 * Row 12 title = Hair
 * Row 12 info = Black
 * Row 13 title = Eyes
 * Row 13 info = Brown. Sometimes depicted as red or reddish.

Personality
Izaya has the appearance and expression of one who is extremely crafty and confident. He is repeatedly described as a handsome man with a beautiful face by other characters in the novels. He claims to love humanity, and greatly enjoys putting people in miserable or chaotic situations in order to observe their reactions. With a thorough understanding of human behavior and tendencies, he is able to determine people's thoughts and predict their reactions with high accuracy. Izaya is cunning and charming but despite this, women are not interested in him and he isn't very interested in women as well. He has a very jolly and mocking personality, speaking informally with most people as if they are close friends and often using nicknames (such as "Shizu-chan" for Shizuo and "Dotachin" for Kyohei Kadota). He even talks like a girl on occasion, especially online where he actually does pretend to be female. He plays on both sides, so that whoever wins, he will have an advantage.

He likes to play twisted versions of chess (usually using a combination of Chess, Othello, and Shogi pieces) with himself in his room, often using the chessboard as a representation of the battles in Ikebukuro, giving him the fitting appearance of one who watches over the world and controls their actions. The rules he plays by are also beyond normal people, which seems to be a metaphor for the way he lives his life. He does not take his chess games to be a serious representation of the world however, as he usually prefers to observe people acting as they see fit instead of controlling them, and he even once set fire to his chess set in his excitement.

Although Izaya enjoys conflict, often showing up wherever there is potential for one, he usually stays out of it, preferring to observe the fight instead of directly taking part in it. However, when provoked, he quickly puts his opponent in his place, simply proving his superiority without actually beating the other person. Therefore he is usually seen as the one starting fights, but hiding in the shadows instead of directly taking part. He uses a flickblade and is skilled in parkour.

Izaya is also known to be one of the strongest men in Ikebukuro, although the title of strongest man belongs to Shizuo Heiwajima. When Mikado Ryuugamine first came to Ikebukuro, Izaya was one of the people Kida Masaomi warned him to stay away from, simply describing Izaya as "dangerous."

Background
Up until middle school in Raijin Academy, Izaya was a model student: the vice president of the elementary student council, the star at sports meetings, and winning independent research awards, poetry awards, slogan awards, and participated in essay contests. This combined with his good looks and a respectable family made him well known, especially with his girl classmates. However, Izaya was not particularly loved or hated since he went through school life in a withdrawn state, preferring to observe everything from afar, carrying out his life philosophy to be 'neither too close nor too far' from the others.

During afternoon breaks and such, other students would talk in the classroom or play in the courtyard, but since Izaya would always be in the library, he gave people the impression that he was a loner. But Izaya enjoyed being a step away from his surroundings. He knew he was a top student, however, he didn't think the people around him were idiots and didn't look down on them.

At this point, his observations are not used for ill, rather a simple hobby, but slowly it was turning more and more into an obsession. His calm life changes after meeting fellow middle school student, Shinra, who immediately assesses Izaya's personality and tries to convince Izaya into creating a biology club. At first, he declines his offer and after that, he continued living the same life he had in elementary school, while keeping an eye on the human called Kishitani Shinra, but one day he suddenly understood: Shinra was his opposite because unlike him, he has no interest at all in human beings. This confuses Izaya who eventually agrees to become the Vice President of Shinra's club so he could study him more closely.

When a club expo was scheduled, Shinra left their presentation entirely in Izaya's hands and, much to Shinra's surprise, Izaya turned the whole club into a gambling ring with one of the other members, Nakura, serving as Izaya's business partner. Shinra tells Izaya to stop but gets brushed off each time. One day, after making a bad bet, Nakura comes in brandishing a knife and threatens Izaya to give back all the money he lost. When Izaya refused, Shinra jumped in the way of the knife at the last minute. It is then that Izaya realizes he is extremely jealous of Shinra because of his ability to separate himself from the world because of his love for Celty. Izaya then asks Shinra to tell everyone that Izaya himself was the attacker and promises to make Nakura pay for as long as possible for what he did. After the incident, Izaya is taken into protective custody and, from then on, continues to create an infamous reputation.

He was later enrolled in Raijin Academy High School with Shizuo, Shinra and Kadota; although, Izaya rarely attended class. He shares a passionate hatred for Shizuo and from nearly the moment they met they tried to kill eachother. Izaya claims Shizuo is the only human he does not love and wouldn't mind seeing him dead. Shizuo tries to kill him every time they meet on the street, meaning Izaya often finds random vending machines, trash cans and other large objects flying straight at him. Shizuo finds him untrustworthy, saying whenever there is trouble, "99% of the time you're (Izaya) behind it." Izaya had often framed Shizuo for crimes he didn't commit, causing him no end of trouble. During this period, Izaya begins to collect "followers" for his own purposes, of which most are traumatized teenage girls, ranged from gothic lolitas to gyarus (though the majority of them simply took Izaya to be a fortune teller of sorts) who would do whatever he said and worshipped him in an almost cult-like fashion (like Saki). Most of them were usually depressed and/or suicidal and have all been victims of pretty severe levels of violence from their families or lovers. Those girls were lost and desperate for someone to believe in, making them especially easy to use. They weren't really in love with the families or boyfriends concerned, they simply put their faith in them. All Izaya did was shift their faith to him. If he wanted them to die, they would probably have gone ahead and died, even if they had doubts. Izaya's fans conflict between the students in several Ikebukuro high schools, leading to a protracted period of unrest. Shizuo rises to local fame after he becomes the center of this conflict despite his wish to remain outside of it.

He is also a member of the Dollars. Although Mikado Ryuugamine is the leader of the gang, Izaya is the one who anonymously recruited most of their members when Mikado stopped doing it, sending out invitations saying the Dollars have no rules except that you have to say you are one of them. Izaya is usually seen talking about the latest rumors of gangs, urban myths, and otherwise stirring up trouble in online chatrooms while at the same time pretending to be a girl. His screennames are "Kanra" and "Nakura", and most recently "Chrome."

Shizuo Heiwajima

 * Main article: Shizuo and Izaya

Shinra Kishitani

 * Main article: Izaya and Shinra

Mikado Ryūgamine

 * Main article: Mikado Ryūgamine

Izaya and Mikado met on the internet. However, Mikado does not know who 'Kanra' is in real life at first. Mikado met Izaya face to face on Mikado's second day in Ikebukuro. Izaya knows that Mikado is the leader of the Dollars, but promises not to sell the information to anyone, although he doesn't keep this promise and tells Kida Masaomi. In the manga Izaya tells Mikado that it wasn't a coincidence that he met him - he was looking for him.

Later in the novels, Mikado begins to rely on Izaya's information and advice. This is similar to how Masaomi depended on Izaya to lead the Yellow Scarves which eventually led to his downfall; Vol. 7 foreshadows that Mikado will be led down a dark path because of Izaya. However, in the same novel, Aoba reveals that both he and Izaya have grossly underestimated Mikado.

Mairu & Kururi Orihara

 * Main article: Kururi Orihara, Mairu Orihara

Kururi and Mairu are Izaya's younger twin sisters. They grew up in the same house as Izaya, where all three siblings are said to have had "fairly normal parents." Izaya believes that their eccentricities are because of his influence on them, having told them as children that they were copies of each other and therefore had no real purpose. When they were younger, he often had to take care of them because their parents were almost always working abroad. Izaya states that aside from Shizuo, they are the only humans that he doesn't know how to deal with, which may explain why he's annoyed by them. While Mairu and Kururi are inseparable, their feelings on the elder brother are not as clear-alternately stating that they still consider him family, but also saying they wouldn't mind killing him and throwing his dead body in the garbage to meet their idol: "Hanejima Yuuhei", Shizuo's younger brother.

Namie Yagiri

 * Main article: Izaya and Namie

Dollars/ Mika Harima arc
He was first stated dangerous from Masaomi. When Rio went with the kidnapper 'Nakura', Izaya is seen spying on her from a cafe.Izaya calls Celty and tells her not to kill the kidnappers, just to scare them a little. She rescues Rio, who comments that riding on the bike with the Dullahan is surreal. Celty then drops Rio off at an abandoned building, where Nakura (Izaya) is waiting for her.

On the roof, Izaya introduces himself to Rio as Nakura, and after confirming that he organized the rescue, asks if she was scared, to which Rio replies yes. Izaya then reveals that he orchestrated the kidnapping as well as the rescue, then tells Rio that since she wanted to die, she accepted the kidnapping as her 'disappearance'. However, he points out, she now was thrilled she was still alive.

Izaya tells Rio that he loves all humans, not just her specifically, and that he just wanted to see the look on her face when he told her what he did. He then takes Rio to the edge of the roof and shows her the stain on the ground below, where others had jumped to their death. "Everyone lies, everyone hides things, no one goes through this life completely honest," says Izaya, so why should she be able to keep secrets but it's not ok for her dad to have his? Izaya then leaves the roof, promising Rio that she was just as ugly, immature, and boring as he thought she would be. Rio thinks that she could get back at Izaya by actually jumping, and does. However, Celty catches her in a net of shadows.

On a park bench, Izaya tells Masaomi "it's been a while." Masaomi then introduces Mikado to Izaya, and Mikado recognizes Izaya's name as the person he is absolutely not supposed to piss off. Masaomi asks Izaya what he is doing in Ikebukuro, and Izaya responds that he came to see someone, and that someone is Mikado.

Suddenly, a large trash can comes flying and hits Izaya. A man in a bartender uniform tells Izaya that he told him never to set foot in Ikebukuro again, to which Izaya replies that even though he framed "Shizu-chan" for something he didn't do, he shouldn't get so mad about it. The man tells Izaya not to call him that, as his name is Shizuo Heiwajima. As Izaya readies his knife, a group of gangsters with the man from before come to attack Izaya. However, when they see Shizuo, one of them looses control and attacks Shizuo. Shizuo proceeds to attack all the gangsters, and in the chaos, Izaya begins to get away. Then in the chat Izaya as Kanra tells TarouTanaka to stay away from the Dollars. In a hospital, Izaya visits a pale girl. She is surprised and glad to see him, then tells Izaya that "he" hasn't visited yet and only walks to the corner but never enters the hospital. Izaya says he's sure "he" will come. The girl's phone has a picture of her with Masaomi. Izaya picks up a call from a guy on th street sleeping and Kyohei calls the cell of who he thought as Kazutano. Izaya tells kadota where he his then Izaya is chased away by SHizuo.

Namie goes to Izaya Orihara's apartment where tells her quite a bit about herself, such as her name and that she is the chief of the 6th lab at Yagiri Pharmaceuticals, despite this being their first meeting. He hopes the list of illegal aliens he gave Namie was helpful, but she interrupts him demanding that he help her find Seiji. Rather than assist, Izaya informs her of more pressing matters, like the talk of Nebula buying out the Pharmaceuticals. He reveals he knew her uncle lost the company after taking some dangerous risks, and Namie entered the company on the bottom level and worked her way up, then tells her not to meddle with Seiji. She insists she is trying to help him, only to have Izaya say the stalker always thinks they're helping the stalker. Namie is furious at being compare to a stalker. He decides to help, but only in the way he sees fit. Upon seeing a mix of chess, shogi and othello pieces with a go board on Izaya's table, she asks what he's playing, but he ignores her and asks if she's jealous of the scarred girl. She denies this.

Izaya easily finds where Seiji is - in possession of the police. When she receives a call and leaves his apartment, Izaya moves a shogi piece on his gameboard. Later, Izaya twirls in his chair, thrilled that there are so many plots in Ikebukuro that even he knows nothing about. He states how much he loves humans and that they should all love him back. He excitedly moves a shogi pawn to be surrounded by Othello pieces.

Izaya arrives with Celty Sturluson, who punches the guy so Izaya can jump on him. The girl runs away, furious. Izaya informs Mikado he was hoping to run into him but met the black rider here, too. Mikado knows she is after the girl he took home and quickly begins walking home, only to be followed by Celty and the infobroker. They stop in a tunnel when Mikado wonders why they are following him. Izaya's phone rings, so Mikado ends up talking with Celty about the girl.

Mikado offers to go in first to clear things up with the redheaded girl so she doesn't think he betrayed her, but when he arrives in his room, the girl is gone. Two men grab Mikado and hold him to the floor. Izaya remarks to Celty that it was the first time he heard her name while throwing rocks at her motorcycle. She doesn't believe him and tells him off for throwing rocks at her horse, again to Izaya's interest. He notices a cleaning van in a run down place like Mikado's and wonders what's taking him so long.

Izaya and Celty arrive in his room just as the 'cleaning' men exit the window. Celty starts to go after them, but Izaya stops her, claiming they were from Yagiri Pharmaceuticals. Mikado realizes who the Pharmaceuticals were and rushes to his laptop, open to the Dollars homepage. When Celty asks what he is doing, he responds that he never wanted to be normal. Izaya watches, having only half believed the rumors. Mikado decides all his cards are in order as Izaya laughs, saying he hit the jackpot.

At the Dollars meeting, Izaya finds everything fun. The members (including Izaya) have received a text saying 'everyone who is not looking at their phone is an enemy. Do not attack'. Seiji is furious to find Mika is not the head of Celty. Izaya laughs and remarks that he couldn't even tell the difference, so their love must not have been very strong.

Izaya observes the chaos from the Dollars meeting and invites Kyohei Kadota, whom he calls Dotachin over. Although Kyohei gets mad at the use of his nickname, he accepts Izaya's question regarding the origin of the Dollars' name. He thought it stemmed from "give me all your dollars", but the real root is "dolla dolla", meaning to do nothing. Walker Yumasaki and Erika Karisawa arrive and wonder if they hallucinated the whole meeting.

Izaya then speaks with Mikado. The infobroker was surprised at the turn out at the Dollars meeting. He reveals his knowledge of the reasoning behind Mikado's move to Tokyo, but informs the student all this commotion will seem normal in a few months. Mikado would have to move to more underground activities to stay interested, but would soon get bored of that, too. "The only way to truly escape the mundane is to always be evolving." Izaya decides not to charge Mikado for Namie's private cell number and won't tell on him being the leader of the Dollars. He then hides behind Mikado as a large object comes flying toward him, courtesy of Shizuo Heiwajima. Izaya wishes Mikado a good day, calling him Taro Tanaka and revealing his status as one of Mikado's chatmates.

At his apartment, Izaya comments how Namie threw away everything for her brother's love. He provokes her by reminding that Nebula is planning to merge with Yagiri Pharmaceuticals, which would prove problematic should they receive wind of the Mika incident. It is revealed that he was the one texting and calling Mika, advising her on how to stay with Seiji. He moves several pieces on his mixed gameboard and regrets the inability of the kings to directly fight one another. He believes himself to be similar to Namie's uncle, in that they both are skeptical but greatly desire the after life.

Izaya notes that Dullahans are always female, and asks Namie what she knows of Dullahans. According to Izaya, they are Valkyries fallen to earth. Celty's head is asleep but alive because she is waiting to wake up during a war to guide her warrior to Valhalla - and Izaya plans to be that warrior. He will start a war only he can win, because although he doesn't care whether he goes to heaven or hell so long as he exists, he would prefer heaven. He then holds Celty's head in his hands and muses that Celty will never expect to look for her head within her gang - the Dollars.

Saika Arc
Shuiji Niekawa comes to Izaya's office asking him who's the strongest man in Ikebukuro. Izaya tells him Shizuo is the strongest and then sends Shuiji to Celty because Izaya didn't want to talk about Shizuo.

8 years ago, After destroying the Raira's soccer field, Shizuo met Izaya, Shinra's friend from middle school. Shizuo instantly dislike him and attempted to punch him, but Izaya responded by slashing Shizuo's chest with his knife. Izaya said their fight was indeed a blast. Shizuo proceeded to chase him through the streets of Ikebukuro, then was run over by a truck. Izaya paid the driver, who was shocked.Shizuo arrived at Shinra's apartment and broke down his door while Celty tried to calm him down. Shinra was excited to see Shizuo although Izaya was at his place, too. Izaya was amazed Shizuo could still stand after their fight.

Izaya framed him for a crime he didn't commit, but the police soon realized his innocence and released him. In the present Celty asks Izaya about the slasher. Izaya at first teases her anout Shinra being preverted. Then he tells her about Saika and the demon blades. That night Shizuo gos to Izaya office yelling at Izaya to come out. Izaya comes out and Shizuo says he's going to kill Izaya.

Izaya tells Shizuo its bad to be the playground bully. Then Celty comes in showing Shizuo the slasher is still out there Shizuo leaves Izaya alone and hunts for the slashers.

Yellow Turban Arc
2 years earlier Izaya meets Masaomi Kida and tells Masaomi where the Blue Sqaures are hiding out,and helps Masaomi out in a gang war. Then Izaya a couple days later sees Saki in the hospital and teases Masaomi about he can never runaway from his past. Masaomi tries punching Izaya but he dodges and throws Masaomi to the ground. When Masaomi got up Izaya left.

In the present Izaya comes to his office to see Namie being held hostage by Shingen. Izaya talks to Shingen about the head. Then Shingen leaves with a toy gun in his hand. A couple days later Masaomi comes to Izaya's office asking him who's the leader of the Dollars. Izaya tells him it's his friend Mikado. Then Masaomi leaves in shock. It is later revealed that Izaya caused the accident with Saki being kidnapped by the Blue Sqaures.

Hollywood Arc
Izaya takes a back seat to the events that happen in arc. The only prominent appearance he makes is telling Namie about his Sisters. He also tells the others in the chatroom about a 10 million yen reward that was put out for Celty by Yadogiri Jinnai. By the end of the novel, Izaya is upset by the fact that so much happened without him getting involved. As if to add insult to injury, Shinra and Celty invited almost the entire main cast over to their apartment for a hotpot party (including his Sisters and Shizuo) but neglected to invite him. He asks Namie if she wanted to have a hotpot party with him but she only brushes him off.

Akane Arc
Making a comeback from volume 04, Izaya is one of the main driving forces behind the events of volumes 5 and 6. He first manipulates Akane Awakusu into attacking Shizuo knowing full well that Akane would mention his name. When Shizuo storms off to Izaya's office, Izaya simply leaves a crudely written note that he switched to a different building. Shizuo rushes off to Izaya's new "office" only to find several dead bodies strewn across the floor. The room is revealed to be one of the many offices of the Awakusu and one of it's members sees Shizuo standing over the bodies of his colleagues. This prompts the Awakusu to hunt Shizuo down mercilessly while Izaya watched the fireworks. To his surprise, Shizuo doesn't fight back when the Awakusu confront him and simply runs away. Izaya expected Shizuo to fight back in full force and is a little annoyed at how Shizuo was able to anticipate that a violent reaction would only make him look even more guilty than he already was.

Izaya also sends Masaomi Kida and Saki Mikajima to look up information on Yadogiri Jinnai. While Kida is out of the city (and away from the chatroom) he hacks into Kida's account and impersonates him on the chatroom to manipulate Mikado similar to how he manipulated Kida during the yellow scarves incident.

Dollars and BLue squares arc
After Akane is saved and the attacks on Dollars have stopped, Izaya suspects that the Awakusu will probably start looking for him if Akane tells them his name. He leaves Ikebukuro for a while to follow another lead on Yadogiri but gets a phone call from a private number. His caller passively aggressively taunts him, calling Izaya a horrible information broker due to how obvious it is to spot him in a crowd. Just as Izaya realized that the voice is coming from behind him and not just his phone, he feels a knife being thrust deep into his chest by none other than Yadogiri Jinnai himself. Yadogiri states that this is punishment for interfering with his plans. He also states that Izaya should learn his place saying that while he is a god in Ikebukuro and Shinjuku, he is little more than an ant on the grand scale of things. Yadogiri leaves Izaya bleeding on the sidewalk as he walks away. Izaya tries to call Namie but passes out before he can reach his phone.

Izaya in the Hosipital and Namie VS Mika Arc
Izaya is recovering in his hospital bed. He pesters Shinra by calling him due to boredom but gets brushed off each time. As the days go by, he goes into a state of disillusionment and begins to wonder who will come to finish him off. He suspects either Shizuo or the Awakusu to come busting in to strangle him but instead finds a girl who he doesn't recognize. The girl with a knife in her hand states that Izaya tricked her into "dying" with him several months ago (much like how he did with Rio Kamichika) but left her unconscious in a park somewhere. She wanted to see what a man like him was like when faced with death and found him after she saw a report about his stabbing on the news. Izaya is initially perplexed but is soon starts laughing hysterically. Izaya, finally recovered from his state of disillusionment, thanks the girl repeatedly for "exceeding his expectations." He is amazed at how someone so insignificant would harbor such an intense hatred of him that it would last for over a year and prompt her to look for him. His love for humans revitalized, Izaya disappears from the hospital room along with the girl to proceed to his next plan.

Adabashi Arc
Izaya isn't really seen much in this Arc other than near the end. In his apartment, he holds a gathering of several individuals who have a grudge against the dollars or someone in the dollars (many of them were former dollars members themselves). These people include:


 * Namie Yagiri (for obvious reasons)
 * Ran Izumii: the former leader of the blue squares. He states that he is only there to kill Kyohei and his gang along with Aoba and Izaya himself. However, he states that he'll work with Izaya for now to get to the others on his list.
 * Mikage Sharaku: An acquaintance of Izaya's from highschool. During that time, she was one of several girls who worshiped Izaya in an almost Cult-like fashion. Her exact feelings towards him now are unclear but Izaya speculates that she hates him due to the fact that he got Mikage involved in an incident that forced her to drop out of high school. She and her brother are also the martial arts teacher of Mairu and Kururi.
 * Haruna Niekawa: She wants revenge on Anri as well as the location of Takashi Nasujima. Izaya has promised her both.
 * Adabashi Kisuke: A stalker of Ruri Hijiribe who was formerly working under Yadogiri Jinnai. He wants to get payback from Mikado for lighting him on fire and also want to kill anyone close to Ruri.
 * Slon: Vorona's former partner. He isn't there by choice but was ordered to keep tabs on Izaya for the Awakusu.
 * Kine: A former member of the awakusu. He first met Izaya after stopping one of his and shizuo's many fights during highschool and was responsible for jumpstarting Izaya's early career as an information broker.
 * Dragon Zombie: A semi-large gang that have remained under the radar until recently. They operate as body guards for Izaya in case Yadogiri decides he wants to finish Izaya off. They're basically henchmen.
 * Izaya also officially leaves the chat room as Kanra and takes up a new alias in the form of Chrome.

Dragon Zombie arc
This Arc deals mostly with Izaya's past and how he came to be what he is along with his history with Shinra. At the start of the novel, Izaya is tasked by the Awakusu to gather information on two groups. The first group is "Amphisbaena" which is running some kind of illegal gambling parlor in Awakusu's territory. The second is an unnamed group which is distributing a dangerous drug called "Heaven's Slave" also in Awakusu's territory. Izaya accepts the job and meets with Celty to ask her for a favor. Izaya asks the courier to protect his sisters for the next couple of days. He also gives Celty a laptop which she is supposed to keep safe until tomorrow. Celty is visibly shocked at how Izaya is actually showing concern for his family but quickly accepts. Izaya continues his job but is quickly captured by "Amphisbaena." For most of the novel, Izaya is repeatedly grilled for information about himself as well as who hired him to go investigating them by a woman who calls herself "Earthworm." Throughout the interrogation, Izaya has several flashbacks to when he and Shinra were in middle school as well as the incident which ended with him stabbing Shinra.

Izaya and Shinra first met in middle school where, with Shinra's constant prodding, they started a biology club together. After summer break, there was supposed to be a school festival showing what the clubs were capable of. Shinra left Izaya in charge of the presentation. Instead, Izaya along with an aquantance of his named Nakura started a small gambling ring where people would bet on the outcome of baseball games (kind of like how people bet on horse races). Shinra found out and attempted to put a stop to it but Izaya kept ignoring him. One day, Nakura, who lost a lot of money on the gambling, came into the club room with a knife, threatening Izaya to give the money he lost back. Izaya denies Nakura which prompts him to rush at Izaya with the knife. Shinra jumps between them at the last minute and gets stabbed by Nakura in the process. Nakura runs out in a panic while Izaya bandages Shinra's wound with Duct tape and calls an ambulance. Before he makes the call, Izaya asks Shinra to tell everyone that he was the one who stabbed him. Shinra agrees but questions why. Izaya simply replies that in return, he'll make Nakura suffer for as long as he can. He takes the heat for the stabbing and uses that to blackmail Nakura into working for him. This is also where Izaya got Nakura as his screen name.

Back in the present, Earthworm is interrupted by the arrival of Izaya's other target, the leader of the group that was selling "Heaven's Slave." The man identifies himself as Shijima and states that he's there to kill Izaya once and for all. When questioned about how he found them, he stated that he and his men stolen a laptop from the headless rider that contained Izaya's research into Amphisbaena and the whereabouts to this gambling parlor. Both of them are interrupted by a phone call to earthworm. The man on the other end of the phone claims to be the real Izaya which throws Earthworm and Shijima into a state of confusion. The "Izaya" on the phone implies that the man tied up on the chair is not Izaya but really the boss of "Amphisbaena." Earthworm hastily removes the bag to reveal...Izaya, smiling maniacally. Before Shijima and Earthworm can say anything, the door to the parlor is busted down and the room is invaded by several individuals in leather jackets. Izaya shakes the ropes loose and joins the Dragon Zombie members standing next to the door. Afterwards, Izumii with a cell phone in his hand and Sharaku Mikage enter the room as well. Shijima orders his men to attack but they are all easily dispatched by Mikage's fists. Earthworm also orders her subordinates to attack but they simply do nothing but stand there and stare with glowing red eyes.

Earthworm attempts to kill Izaya with two broken bottles but Izumii easily incapacitates her. Afterwards, Izaya persuades Shijima to join forces with him. In return for providing the dollars information network, Shijima would provide financial backing as well. Outside the gambling parlor, Izaya meets up with Haruna Niekawa and compliments her on getting control of Earthworm's subordinates. He then orders her to take control of Earthworm as well promising to let her see Mr. Nasujima if she does.

Izaya separates from the rest of the group to head back home on his own. He reflects on Celty's comment about his showing concern for his family but quickly disregards it. He knew Celty would get suspicious about the laptop so he asked her to keep an eye on his sisters as a way to keep Celty busy. He also reflects on his relationship towards Shinra remarking that Shinra may be the only person Izaya actually considers a friend and not just another one of his "humans". He also realizes that, due to his plans to involve Celty in an all out war, Shinra might end up cutting all ties to Izaya completely. At the prospect of losing the only person Izaya calls a friend, Izaya begins to laugh hysterically only to suddenly stop and punch a nearby lamp post, bruising his hand in the process. Before he can elaborate more on his feelings, Izaya's sisters spot him and call out to him. Izaya puts on his usual smile as his sisters thank him for asking Celty to protect them. Izaya simply shrugs as the three of them walk back to his apartment.

Kadotas' Coma Arc
While on her way to break Shizuo out of jail, Vorona comes across Izaya and deduces that he was the one behind his arrest. Vorona and Izaya begin a very fierce but brief skrimish through the streets until Shizuo and Kuzuhara intervene. Much to everyone's (particularly Izaya's) surprise, Shizuo pays him almost no attention whatsoever and focuses on trying to calm Vorona down. Shizuo explains the situation and rides off with Vorona. Izaya is visibly irritated at how Shizuo was actually able to think reasonably when he was around. At some point later in the novel Izaya is attacked by Slon who is under the control of the corrupt officer named Kujira who was responsible for arresting Shizuo. It is revealed that Kujira is another rogue child of Saika different from Haruna or Anri and that he is working with Yadogiri Jinnai. Kujira orders Slon to finish Izaya off. As the arc ends, it is unknown if Izaya is alive, dead, or possessed by Kujira's Saika.

Saving Izaya / Haruna is back arc
Izaya is ambushed by Slon and knocked out. However, Izaya is woken up after Slon uses him as a club to incapacitate several dragon zombie members. He fakes still being knocked out in order to avoid serious injury while Mikage and Kine manage to chase Slon out of the office.

Later, in an extremely rare case of self doubt, Izaya goes to the hospital to get a CT scan to check his brain for any tumors or abnormalities. After the doctors tell him there is nothing medically wrong with his brain, Izaya takes comfort in the fact that his personality is the result of his own nature and not the result of brain damage.

Near the end Izaya told Anri what he is going to do with Mikado and Masaomi. Which turned Anri into a wreck when he did. What he did made Erika pissed so Erika stood up for Anri and told Izaya that she was Anri's friend and would support her.

Trivia

 * His name comes from a combination of the biblical Isaiah and Japanese for "the one who looks over the crowd".
 * He can speak Russian fluently with Simon, usually proverbs, along with English.
 * His favourite food is fatty tuna. He prefers foods that taste bitter, and dislikes sweets and conserved food. Although unshown yet, his fervor of humanity observation is stated to be reflected in attempt of analyzing people through their prefers and preparation of food.
 * He dislikes Shizuo Heiwajima and eyes of dead fish.
 * He is a light sleeper.
 * He has (at least) ten cell phones.
 * Izaya is known to be one of the strongest men in Ikebukuro, although the title of strongest man belongs to Shizuo Heiwajima.
 * In the episode 25 OVA Erika Karisawa believes that Izaya would be the "Uke" in a yaoi relationship with Shizuo.
 * Izaya's nickname for Shizuo, "Shizu-Chan", wasn't actually made by Izaya himself. He heard about Shizuo from a girl who used to be in Shizuo's elementary school who referred to him as "Shizu-Chan". Izaya initially suspected Shizuo to be a girl until someone explained who he was.
 * Izaya is shown watching Hanamaru Kindergarten in the anime
 * Izaya shows little interest in drinking or partaking in vulgar events.
 * He has a life insurance policy.
 * In the novel, from Mikado's perspective, it is stated that he found Izaya's appearance rather odd for a man of his age, regarding style. And that he seemed different from the rest, since Izaya didn't seem to find an interest in appealing to the culture's fashion.
 * It has been stated that Izaya views Namie as a housewife, not a friend and holds no romantic interest in her, calling her an awful person.
 * He is an atheist, stating that there is no proof that God exists. Regardless, due to following events and his plans, he takes a primarily agnostic view of afterlife later.
 * His eyes are stated as reddish-brown, however, sometimes in the anime, his eye color is just brown as seen as in episode 3.
 * Baccano!: In one of the baccano light novels, Boss Buraido mentions exchanging information with "Orihara of Shinjuku" who is obviously Izaya.
 * Izaya's seiyuu, Hiroshi Kamiya, also did the voice acting of Hiroomi Souma from the anime Working!!, mostly known for his ability to find people's secrets and makes them to do his job by threatening them using the secret, similar to Izaya's ability to gather information and his ability to make people do as he planned, respectively. Also, Hiroomi likes to observe people ever since he was a kid, similar to how Izaya really likes human observation. In the series, Hiroomi states that "Cell phones are wonderful things", and Izaya is known to have ten different cell phones.
 * In Working!!, one of the very few people on whom Hiroomi's blackmailing doesn't quite work is Sato Jun, his partner in the kitchen. Jun has blonde (dyed) hair, is a heavy smoker, and the reason he does not give to the blackmailing is because he freaks Hiroomi out when he tries by hitting or hurting him in some way, usually with cooking utensils. He is voiced by Ono Daisuke, who also voices...
 * Izaya is known as a troll, the series taking a strong hold of realism when it comes to societal behavior. Fans of the series comically call him Trollzaya. The Japanese fandom called him Uzaya, coming from uzai which means annoying.
 * He has been quoted to weigh himself after his every day baths.
 * His favorite fruits are red apples.
 * He and Shizuo both have shared an undeniable hate for one another ever since their school years.
 * Izaya has stated in the novels that he does not hold an attraction for any individual. Though, it is hinted in the novel that he may or may not have had something with Mikage in high school. Narita has been quoted saying that Izaya has normal sexual urges, although he may possibly be aromantic.
 * His favorite quote is: "It is absurd to divide people into good and bad. People are either charming or tedious." - Oscar Wilde, Lady Windermere's Fan.
 * His hobby: Human observation.
 * He sang Subarashii Hibi in the rapping CD.
 * All of Izaya's online handles are "borrowed" from other people.
 * In the anime, Izaya's coat is about as long as his waist, in the novels, most of the artwork depicts his coat as being much longer, reaching his ankles. In manga he's seen with both long and short version of the coat - long coat and short jacket.
 * Izaya Orihara's birthday is on May 4th while his voice actor Hiroshi Kamiya's birthday is on January 28th. However, Shizuo's birthday is January 28th while his voice actor Ono Daisuke's birthday is May 4th.
 * A fan asked Narita Ryohgo (creator of  Durarara!!) if Izaya has had any past love experiences and Narita replied that if he answered that question, it would be a bit of a "spoiler".