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 (Manga and Anime) 25 (Novel)
 * Row 2 title = Job
 * Row 2 info = Informant (Information Broker}
 * Row 3 title = Height
 * Row 3 info = 175cm (5'9)
 * 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) (1986 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, an appearance which he lives up to. 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 occassion, especially online where he actually does pretend to be female. He plays on both sides, so that whoever wins, he will have an advantage.

Although Izaya 'loves' all humans, he has no interest in loving individuals, even his own family, whom he considers as friends. In the novel, he briefly narrates in the beginning of a chapter, stating that he loves humanity, but that if an individual were to love him, he wouldn't be able to return their concentrated love, but would much rather love the individual's enemies and rivals, in a sense of dawning interest. He finishes with a short and subtle plea representing suicide (not his of course) and that he wishes for them to stay and not stop loving him, because he can't bear losing the only person who returns his love, but again, not romantically since Izaya is rather despised and it's been shown in the series, he is alone. Also, Izaya will always keep a thick wall around his heart for that person.

In the novel, is also stated that maybe he feels lonely but at the same time satisfied. His love has been, is, and will always be unilateral. It's not that he's never been loved, however, he always denies such access to him. As long as he loves others, he feels connected to them and satisfied. When he wants to use a person, he does allow them to get close to him, but always keeps a certain distance. Even if someone tries to persuade him to change himself, he would probably never let their words sink into his heart. What Izaya feels for his own person is still a mystery.

He also has a masochistic side, claiming that even if his beloved humans treat him like a worm, he would still 'love' them. Moreover, he adds that maybe one day he'll be able to meet someone whom he would be dying to be used by and since he's in love with all human race he could survive on his masochistic pleasure alone even if he's used. Even so, if someone were to act diffrently than he anticipated, then he might become interested in them (such as the case with Shinra). And if this person piques his interest or he enjoys to tease them that much, then he might actually show love for them while showing love for humans. So he would show some more "attention" or "physical" love for them, yet still keep an eye on his lovely human specimans.

Izaya Orihara likes to play a twisted board game which involves moving a combination of Chess, Othello and Shogi pieces on a Chinese Go board. He plays this game by himself in his room. The combination of games may be a representation of the many plots being acted out throughout Ikebukuro, illustrating how Izaya watches over and manipulates the various people''. ''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 think his board game is a serious representation of the world, however, as he usually prefers to observe people acting as they see fit instead of controlling them, once even setting fire to his board game 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 mid-lock knife (when opened a locking arm with a hook moves in to place so that the blade does not move - when closing, the metal tab on the back of the knife is pushed to release the knife from the hook) and is skilled in parkour. It is implied that Izaya is the only one capable of leaving numerous cuts in Shizuo's bartender suit after a fight in the novels. In the anime, he shaves a gang member's head bald without him noticing it.

Though in the novel, and manga, Izaya states that he is atheist, however in the anime and his own elaboration of his goals, suggest that Izaya is along the lines of an agnostic, speaking of wanting a warriors death to go to Valhalla, once he starts a war in Ikebukuro, and Celty's head wakes.

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 another 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 Heiwajima

Since Shizuo is "violence itself", Izaya despises the fact that he cannot control him, like other humans, with words (thus seeing Shizuo on the level of a beast). He went to Raira Academy with Shizuo, Shinra and Kadota. According to Shinra, Izaya and Shizuo hated each other with a passion almost from the point they met, which was during their high school years at Raira Academy. They met via Shinra, and Shizuo felt a strong surge of resentment towards Izaya and aimed a punch at him. Izaya returned the favor with slashing his shirt with his knife and a murderous relationship began.

Shinra Kishitani

 * Main article: Shinra Kishitani

Shinra went to Raira Academy Middle School with Izaya and has been his friend since then. He finds Izaya and Shizuo's fights amusing. In volume 09 of the light novels, it goes a bit deeper into their relationship. When Izaya first met Shinra, he felt an extreme sense of jealousy at how detached Shinra is from the world. Shinra was able to view humans on a different plane as if he was above them which is what Izaya wanted but was (at the time) unable to accomplish. After the incident in which Shinra got stabbed, Izaya still felt a bitter jealousy towards Shinra but he also still considered him a friend. In fact, to Izaya, Shinra is the only person he actually considers a friend by normal standards and not just another "human".

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

Durarara!!
Volume 01: Masaomi calls him the man who you never want to make contact with. He talks to Masaomi and Mikado. Then he meets two girls that were planning on suicide.Izaya messes with them and says that there is no heaven and he's not planning to die. The girls got angry but the poison he gave them kicks in and they become unconcious. Izaya then pushed the empty suitcases off a building and proves that he loves humans. Later Izaya orders Celty to dump the still unconcious women on a park bench.

Volume 02: Izaya pushes Mikado into a bunch of bullies. Then He stomps on a bullies phone. Then Shizuo attacked him. When Simon comes in, Izaya escapes.

Volume 03: He helps Namie find Seiji. Then later stalks Mikado,and saves him from being kidnapped.

Volume 04: He finds out that Mikado was the leader of the dollars. But doesn't frame him. Then Izaya talked to Kyohei, and messes with Seiji. In the end of the volume Izaya keeps Celty's head,and tells Namie that he wants to go to a heaven with her.

Durarara!! Saika Arc
Volume 01 Saika: He thinks the spammer is an troll. Then helps Shuiji in his interview,and says that Shizuo is the strongest man in Ikebukuro. Then says he dosen't want to talk about Shizuo so he suggests that he should go to Celty Sturlstien. He is a canidite for being the strongest man in Ikebukuro. Then he bans the troll from the chat, but it comes back.

Anime
Anime specific spoilers about this character per episode.

Episode 01: He is seen watching the kidnapping of Rio Kamichika. He is stated as "dangerous" by Masaomi to Mikado.

Episode 02: Izaya watches Rio being kidnapped, then calls Celty Sturluson and asks her to do a rescue job for him. Then, he meets Rio on the roof of a building and introduces himself as Nakura. He asks her if she was scared, then reveals to her that he was the one who orchestrated both the kidnapping and the rescue simply so he could see the reaction on her face when he told her that. He tells her that she wanted to die anyway, and had accepted her fate, but now that she is still alive, she doesn't want to die. Rio slaps him, so he holds her over the edge of the building and points out a stain on the ground where others have jumped to their deaths. As he leaves, he assures her that she was just as ugly, immature, and boring as he anticipated. Later, he stops Celty and asks her when she changed professions to be a protecter of the weak, to which Celty asks if he was responsible for the others who jumped as well. Izaya laughs and denies it, but then says that if someone wants to go out like that, who is he to stop them.

Episode 03: Izaya pushes Mikado in front of the bullies, then cuts the strap of one of the girl's bag. He proceeds to smash her cell phone, then cut her boyfriend's hair bald. Masaomi introduces Mikado to Izaya, and Izaya says that he was in Ikebukuro to see Mikado. Shizuo arrives and throws a trash can at Izaya. Izaya calls him "Shizu-chan" and remarks that Shizuo's inability to listen to reason is a bad thing, then prepares to fight using his switchblade. However, gangsters arrive and distract Shizuo, allowing Izaya to make his escape. He is later seen reading a message on his phone.

Episode 06: Izaya goes to a kidnapper and answers the man's phone call from Kyohei. Izaya told Kyohei the location of the kidnapper, then leaves due to Shizuo chasing him.

Episode 07: A flashback shows Shizuo, Shinra and Izaya at highschool. Then, during a soccer game, Shizuo meets Izaya and Izaya cuts Shizuo, forming an instant mutual hatred. The two began their first chase, ending in Izaya tricking Shizuo into getting run over by a car. Later, Izaya was shown framing Shizuo for a crime Izaya had done. At the end of the episode Izaya watched Shizuo on top of an parking garage.

Episode 09: Namie comes to Izaya's office asking where her brother was. Then Izaya found him.

Episode 10: Izaya follows Mikado home, and saves from from being taken away.

Episode 11: Izaya finds out Mikado is the leader of the Dollars.

Episode 12: It is revealed that Izaya is the one who sends the Dollars invitation after Mikado decided to stop leaking the password. He is also discovered to be the one in current possession of Celty's head.

Izaya's Theme: http://www.youtube.com/watch?v=bkexnSEUDGI

Light Novel
Light Novel specific spoilers about this character per volume/chapter.

Volume 01 : For the most part, Izaya's role in volumes 1-3 are the same as in the anime.

Volume 04 : Izaya takes a back seat to the events that happen in volume 04. 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.

Volume 05 & 06 : 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.

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.

Volume 07 : Throughout volume 07, 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.

Volume 08 : Izaya isn't really seen much in volume 08 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.

Volume 09 : Volume 9 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.

Volume 10: 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 novel ends, it is unknown if Izaya is alive, dead, or possessed by Kujira's Saika.

Volume 11: 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 he turned Anri to wreak 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.
 * 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 refered 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.
 * Izaya's hair style is similar to that of Mikado's.
 * In the anime, Izaya always wears his trademark jacket, whereas in the manga and novels, sometimes he wears a long trench jacket. In the anime's special episode 12.5, he wears a normal, casual t-shirt and jacket.
 * 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.
 * In the Durarara!! fanbase, it is common to hear Izaya mislabeled as a sociopath. This is evidenced in the way he behaves, with rare exceptions primarily refusing to establish sympathy in purpose to preventing prejudice and sees people, loving humanity only because he takes an obsessive interest on them, as if they were subjects to his game, only to end him of his boredom. He usually thinks along the line that he is their God, watching over them, and they are his playthings. However, due to the fact that he does not meet all the requirements of a sociopath, he is not one.
 * 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.