Izaya Orihara

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 in the Japanese version and Johnny Yong Bosch in the English.

Personality
He has the appearance and expression of one who is extremely crafty and confident with his black hair and his hazel/brown eyes. 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 each other. 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, most of which most are traumatized teenage girls, ranging 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 worshiped 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.

2 years before the start of the series, Izaya meets Masaomi Kida, the leader of a local gang known as the yellow scarves, through one of his more frequent customers, Saki Mikajima. In desperation, Masaomi asks for Izaya's help regarding a gang war with another gang known as the blue squares. Izaya assists Masaomi initially, but after Saki is kidnapped, Izaya suddenly ceases all contact with Masaomi which results in the yellow scarves being defeated and Saki being severely injured. It is revealed that Izaya had manipulated these events by playing both sides against each other and verbally taunts Masaomi after he visits Saki in the hospital.

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 screen names are "Kanra" and "Nakura", and most recently "Chrome."

Dollars/ Mika Harima arc
Izaya is mentioned by Masaomi in the beginning of the series as being extremely dangerous. Izaya's first actual appearance in the series is during the kidnapping of Rio Kamichika. Izaya had spoken to her under the screen name "Nakura" and convinced her to commit suicide with him. However, he had also hired a group of thugs to kidnap her at their supposed meeting place. Not long after she was captured, he also hired Celty to rescue her and bring her to the roof of a large building to meet her personally.

On the roof, Izaya briefly converses with Rio, slowly revealing that he had not only organized her rescue but also the initial kidnapping, saying it was all to see her reaction. He then proceeds to verbally taunt Rio about her petty reasons for wanting to commit suicide. Izaya eventually leaves, calling Rio a hypocrite for her insincerity in her with for death. Rio decides to jump in an attempt to get back at him, but is saved by Celty's shadows. Celty then confronts Izaya after the incident and asks if he was responsible for others who had jumped from the roof. Izaya denies this and leaves.

Izaya is next seen meeting Masaomi and Mikado on a park bench. He seems to take an interest in Mikado but he is interrupted by a sudden attack by Shizuo. Izaya and Shizuo almost start a fight, but a group of thugs interrupts them and Izaya manages to escape in the ensuing chaos.

A few days later, Namie yagiri, the head of Yagiri Pharmaceuticals, goes to Izaya Orihara's apartment where she asks him for help regarding her brother, Seiji, who had gone missing. It is also revealed that Izaya had been helping her company with it's human experiments by giving them a list of suitable candidates. Izaya mentions more pressing concerns involving her company's financial security, but she insists on locating Seiji. After a bit more teasing, Izaya agrees to help. Izaya easily finds where Seiji is - in possession of the police. When she leaves, Izaya twirls around in his chair, anticipating something exciting is about to happen. Izaya arrives with Celty in front of Raira academy to meet Mikado.

After saving Mikado from some bullies, he and Celty follow him home with the intent on locating a mysterious girl who Celty believes might have her missing head and was last seen running off with Mikado. Mikado agrees to let them meet her but tells them to wait outside whle he talks to the girl. After a while, Izaya notices a familiar van parked outside the apartment building and decides to check in on Mikado. Several thugs who had attempted to interrogate him were chased out and Izaya remarks that they were from Yagiri Pharmaceuticals. It is then that Mikado makes a sudden realization and reveals his nature as the Dollars Founder to the two of them. Izaya appears excited as Mikado asks for their help. Mikado asks Izaya for Namie's

Izaya observes Mikado's plan unfold from the crowd, taking great interest as the situation escalates. Mikado meets with Namie Yagiri and demands she confess to her company's illegal activities, especially those concerning Seiji and the mysterious girl who is now revealed to be named Mika Harima. Things reach their peak when Celty suddenly dives down from the rooftops and reveals her true nature to the city, taking down several of Namie's thugs in the process. Additionally, Seiji suddenly arrives and attempts to attack Mikado to force him to give back "Celty (Mika)"Izaya finally steps in when it is revealed that the girl does not have Celty's head and that she had only been faking it to get Seiji's love. Izaya comments that Seiji's love wasn't as strong as he thought it was as he wasn't able to tell the difference between the fake and the real thing.

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.

Izaya then speaks with Mikado. The infobroker was surprised at the turn out at the Dollars meeting. He understands Mikado's desire to move to tokyo was to escape being "normal", but informs the student all the chaos of the big city will also become 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 the favor and is soon chased off by Shizuo. As he runs, he calls Mikado by his Nickname "Taro Tanaka." which also reveals himself as "Kanra."

At his apartment, Izaya meets with Namie once again. He comments on her situation, giving up all she had for her brother's love and having her company being bought out by Nebula. He agrees to help keep her in hiding in exchange for Celty's head. He also reveals that he was the one who had been feeding information to Mika about Namie's actions which helped her keep out of Namie's grasp for so long revealing Izaya as the indirect cause to the entire incident.

Although he is skeptical, Izaya remarks that he wishes to go to the afterlife and intends to use Celty's head as his key. Izaya theorizes that Dulluhans are actually Valkyries fallen to earth and that the head will awaken once it is taken to a warzone to transport dead warriors to Valhalla. Since Izaya has no access to a war himself, he resolves to start a war in the city, one that only he could win. He claims custody of the head, saying that Celty wouldn't look for it in an organization she was a part of.

Saika Arc
Izaya plays a relatively minor role in this arc. He only shows up towards the end when Shizuo accuses him of being behind the recent slasher attacks. Izaya calmly denies any involvement although Shizuo refuses to believe that. Before Shizuo can attack, Celty arrives, telling him the truth behind the slasher and the two of them ride off. Izaya merely scoffs at Shizuo's attitude, expressing mild annoyance with his growing maturity.

Yellow Turban Arc
Izaya comes to his office to see Namie being held hostage by Shingen. Izaya and Shingen discuss the matter of Celty's head with Shingen expressing interest in Izaya's theory about Dulluhan's actually being Valkyries. He gives Izaya a piece of advice in order to activate the head. Instead of drawing Celty into someone else's war, Izaya should manipulate things so that Celty herself is the focal point of the conflict. Izaya remarks that he had already thought of the perfect way to do so, as Shingen leaves.

As tensions rise between the dollars and the yellow scarves, Izaya continues to watch from the sidelines, feeding information to Masaomi, Mikado, and Horada in order to cause as much chaos within the two organizations as possible. He had been using one member of the yellow scarves, Iga, as a mole to report to him as the situation continued to worsen but it is revealed that Iga was also one of the slasher victims being controlled by Anri. Anri confronts Izaya about his actions, knowing he was behind not just the incident with the yellow scarves, but also with the slasher attacks as he was the one who gave Haruna Niekawa the information she needed to start her attempted invasion. The two fight briefly but Izaya gains the upperhand and escapes. As he leaves, he angrily declares to Saika that he is the only one who can love humanity and that he refuses to share them with a sword.

Not long after leaving, Izaya is eventually tracked down by Simon who punches and scolds him for manipulating the Raira students as he did. When he returns to his office, he notes that Horada had somehow obtained Mikado's Identity as the Dollar's founder, despite never giving him the info. He correctly realizes it was Namie's doing and expressing joy at so many unexpected developments in his plan despite it's apparent failure.

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
Izaya takes a much more active role in the following arc than the previous one. 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 Yodogiri Jinnai. While Kida is out of the city (and away from the chatroom) he hacks into Kida's account and impersonates him on the chatoom 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 Yodogiri Jinnai himself. Yodogiri 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 Hospital 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
Izaya runs into Vorona while on his way back from a job he did. Vorona recognizes him as one of Shizuo's enemies and attacks. A brief fight ensues before being interrupted by Slon who is acting as Izaya's bodyguard. Slon remarks that Vorona had gone soft due to her time in the city but Izaya says that she has only gotten more focused, specifically on Shizuo. He states that Shizuo has become the only target that could satisfy Vorona's desire for battle. After taking his leave, Vorona voices her agreement with Shizuo that Izaya is little more than a flea.

At some point later in the novel Izaya is attacked by Slon who is under the control of Kasane Kujiragi, Yodogiri jinnai's secretary who also has her own Saika. Izaya is knocked out and Slon attempts to take him to Yodogiri.

Saving Izaya / Haruna returns ar
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. After conversing briefly with Mikago and Kine, Izaya leaves the office, saying he has something to do at the hospital.

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.

Izaya goes to see Kyohei at the hospital later that day and runs into Anri and Erika. Izaya taunts Anri, explaining his plans on what to do with Masaomi and Mikado which puts her under extreme emotional stress. Erika stands up to Izaya, saying she was Anri's friend and would support her. Izaya then leaves, seeing nothing more to gain by staying there.

Later, Mikado calls Izaya, asking him about what to do with the dollars in it's current state. As the conversation continues, Izaya asks if Mikado holds any grudge towards him. When Mikado doesn't answer, Izaya tells him about the recent activities of his own group, Dragon Zombie, which causes Mikado to hang up.

Volume 12
Towards the end of the volume, Izaya decides to end his rivalry with Shizuo once and for all. He tracks Shizuo to a large warehouse on the edge of town and continues to observe the situation from the roof of a nearby building. Izaya also holds the controls to a large rane holding a large group of steel beams. He watches Shizuo confront Kasane Kujiragi and Vorona (who had been hired as her bodyguard) about Celty's sudden change. In the middle of the confrontation, Izaya signals for the crane to open, dropping the metal rods on top of Shizuo. However, Vorona notices this and manages to push Shizuo out of the way. Izaya then pulls out a sharpened piece of pipe and throws it at Vorona like a spear, injuring her severely. As Shizuo attempts to tend to Vorona's wounds, Izaya calls him on his cellphone. Izaya taunts Shizuo about his attempts at trying to seem human. Shizuo let's Izaya talk and after he is done insulting him, Shizuo simply tells Izaya "Goodbye" in a calm manor before hanging up. The novel ends as the two face each other one last time before fighting.

Volume 13
Shizuo and Izaya fight. Izaya sets traps for Shizuo, but these are just cover. By various means he had the oxygen from the building removed such that Shizuo now winds up suffering from oxygen deprivation and goes down on his knees. Izaya then very cautiously sets the roof on fire. Celty’s shadow comes down from the sky and douses the fire. Shizuo has punched a hole in the floor to escape. He bats Izaya away with a metal pole. Izaya crashes into the building beside. When he regains consciousness he runs for it; Shizuo jumps straight down the building to follow. Shizuo is rather calm throughout; he doesn’t raise his voice once in this volume.

Izaya and Shizuo reach the area. Everyone steers clear. Shizuo’s show of strength overwhelms the Saika crowd. Izaya is fighting Shizuo head-on for the first time. ‘Float like a butterfly, sting like a bee’ - except he isn’t making much damage for the amount of energy he’s expending. He stabs Shizuo, except it doesn’t go in. By carelessness he doesn’t make it in time to dodge one of Shizuo’s punches, and blocks it with both arms - this is possibly the only reason he survives. Both arms are broken. Further internal injury occurs. Shizuo picks up a vending machine for the killing blow.

Aoba says that even if Izaya loses the fight and dies, he wins anyway, because he gets to prove Shizuo is a monster.

"Do it, monster," Izaya says, but he gets a knife shot at him from Vorona instead. Vorona is about to kill Izaya in Shizuo’s stead, because she’s already a killer, she’s already a beast, and Shizuo is not. She shoots Izaya. A flash grenade goes off - from the Russian chefs, who’ve escaped just in time to intervene.

Izaya was rescued by Manami and Kine, and requests to leave the city, even if he cannot survive the journey.

Aftermath
After Manami and Kine brought Izaya to a hospital, he disappeared few days later, making his condition a mystery to the rest of the story. In the summary of Durarara!!SH, Izaya went missing from Ikebukuro.

Shizuo Heiwajima
Main article: Shizuo and Izaya

Shizuo and Izaya both claim to hate eachother, however their true feelings can be seen as a form of love. they are canon. shizaya is canon.

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

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.
 * 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 Shizuo Heiwajima.
 * Izaya is known as a Internet 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".
 * His current status is unknown. (As of volume 13)