Izaya Orihara

"People think of him like some cold-blooded monster, but he's more human than anyone I know; he's so fragile inside. If you pumped him full of love and betrayal and such, I think he'd fall apart. I think that's why he decided to love humanity by letting everything wash over him. Do you see what I'm saying? He accepts everything, but he doesn't take it in. He lets it wash over him."

- Shinra Kishitani

Izaya Orihara (折原 臨也, Orihara Izaya) is a powerful and skilled underground information broker. He usually gives information for his own enjoyment, and he claims to love the entire human race, excluding Shizuo Heiwajima. He is one of the main antagonists in Durarara!!, one of the founders of Amphisbaena and Heaven's Slave, and a member of the Dollars.

Appearance
Izaya has short black hair and brown eyes. He is repeatedly described as a fragile-looking, handsome man with a beautiful face by other characters in the novels. However, he is also described by the same characters as appearing mischievous or otherwise unsavory.

His regular outfit consists of a black coat with brown fur lining that goes down to his hips, along with a plain black long sleeved v-neck, pants, and dark brown shoes. In the novels, he occasionally dons a longer version of his coat that reaches down to his ankles. In one OVA episode, he is shown to wear a lighter short-sleeved hoodie in warmer weather. In the manga, he goes through many variants of the same coat. They often differ in length or where the lining is, e.g. in some versions it will lack fur on the cuffs or hem.

In the Izaya Orihara spin-off novels, his outfit design has changed somewhat. He now wears a light grey variant of his shirt and a long, black cape that fastens around his neck with a buckle, though he keeps this undone. The cape also comes with a fur-lined hood.

Personality
Izaya claims to love humanity, although his definition of "love" is much different than one would assume. What he specifically loves about humanity is the unpredictability of human nature, and he greatly enjoys putting people in enjoyable 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 his manipulative nature prevents him from making any genuine or lasting bonds with others. He has a 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 Kyouhei Kadota). He even talks like a girl on occasion, particularly online, where he actually does pretend to be female. During conflicts, he plays on both sides so that whoever wins, he will have an advantage.

He likes to play twisted versions of checkers (usually using a combination of Chess, Othello, and Shogi pieces) with himself in his apartment, 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 the actions of others. 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 by 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. Volume four of the light novels shows that he is bitter when large-scale events take place in Ikebukuro without involving him.

Izaya is known to be one of the strongest men in Ikebukuro, although the title of the strongest man belongs to Shizuo Heiwajima. When he needs to protect himself physically, Izaya uses a flickblade and is skilled in parkour and freerunning. Izaya likes to start fights with Shizuo and let Shizuo chase him around. When Mikado Ryuugamine first came to Ikebukuro, Izaya was one of the people Masaomi Kida warned him to stay away from, simply describing Izaya as "dangerous," while in both the original light novel series and manga, he instead confirmed that Izaya was not "dangerous" per se, but more like "unstable." He's a person most of the characters, himself included, could never trust, because they never know what he could or would do.

Background
According to his father, Shirou, at a young age Izaya had no interest in interacting with others, to the point where his parents began to worry. Up until middle school, 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 participating 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 did not think the people around him were idiots and did not look down on them.

At this point, his observations were not used for ill, rather a simple hobby, but slowly it was turning more and more into an obsession. His chaotic life changed after meeting fellow middle school student, Shinra, who immediately assessed Izaya's personality and tried to convince Izaya into creating a biology club.

At first, he declined his offer and kept an eye on Shinra until he suddenly understood: Shinra was his opposite because unlike Izaya, he had no interest at all in human beings. This confused Izaya, who eventually agreed 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. During his time at Raijin, Izaya meets Shizuo as well as a fellow student named Hajime Shishizaki. Shishizaki is said to be the only one who could ever catch Izaya; while also being as strong as Shizuo.

Izaya and Shizuo shared a passionate hatred for each other, 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 each 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 has often framed Shizuo for crimes he didn't commit, causing him no end of trouble. During one of their more hectic confrontations, Kine, a high ranking member of the Awakusu was caught in the crossfire. Kine managed to dissolve the conflict but took an interest in Izaya who was just starting out as in information broker at the time. Through Kine, Izaya met many of his first clients in the Yakuza and was his official contact with the Awakusu.

During this period, Izaya began to collect "followers" for his own purposes, most of which were 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 worshipped him in an almost cult-like fashion (like Saki). Most of these girls were usually depressed and/or suicidal and had 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 that faith towards him. If he wanted them to die, they would probably have gone ahead and did it, even if they had doubts. Izaya's fans had conflicts between students in several Ikebukuro high schools, leading to a protracted period of unrest. One notable incident involved Mikage Sharaku, a classmate who became one of Izaya's followers due to a crush she had on him. The exact details of the event are unclear, however, Mikage took the fall for Izaya which resulted in Mikage's expulsion and inability to find work. Despite this, she later claims that while she finds him to be awful, she respects him because he's true to himself.

At some point, he encounters Kuon and Nozomi and saves them from an abusive foster family. Nozomi later became one of his followers.

At some point during Aoba's middle school years, Izaya apparently claimed to be Aoba's cram school tutor and had come to give his School ID back to him. Aoba knew that this was a blatant lie as he had his ID on him at that time but he didn't want to cause a commotion in his house. He and Aoba stepped out and discussed why Izaya had come. Izaya is surprised that Aoba was able to obtain his personal information through the Dollars network while Aoba is surprised that Izaya tracked him down so quickly. Aoba and Izaya immediately begin to dislike each other mostly due to the fact that their personalities are too similar.

2 years before the start of the series, Izaya met Masaomi Kida, the leader of a local gang known as the Yellow Scarves, through one of his more frequent customers, Saki Mikajima. Izaya ordered Saki and Nozomi to date Masaomi and Koji respectively to manipulate the Yellow Scarves, but Nozomi dumped Koji soon afterwards. In desperation, Masaomi asked for Izaya's help regarding a gang war with another gang known as the Blue Squares. Izaya assisted Masaomi initially, but after Saki was kidnapped, Izaya suddenly ceased all contact with Masaomi which resulted in the Yellow Scarves being defeated and Saki severely injured. It is revealed that Izaya had manipulated these events by playing both sides against each other. He verbally taunted Masaomi after he visited 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" (which he bought from the actual 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. The kidnapping of Rio is an anime specific event which deviates from the original light novel. In the original light novel, he makes a suicide pact with Manami and another girl. Izaya had spoken to the two under the screen name "Nakura" and convinced them to commit suicide with him. This 'pact' however, it merely a ploy. He exposes his plans to the two as the drugs he planted in their drinks begins to kick in. He later has Celty cart their unconscious bodies home. In the anime, he had hired a group of thugs to kidnap Rio 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, and to reveal to her that she still has the will and desire to live. Izaya eventually leaves, calling Rio a hypocrite for her insincerity in her wish 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 sees Mikado about to save Anri from a group of ganguro girls and helps intervene. After scaring the bullies away, he has only a few moments to talk to Mikado before being attacked 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.

In the anime, Namie Yagiri, the head of Yagiri Pharmaceuticals, goes to Izaya Orihara's apartment where she asks him for help regarding her brother, Seiji, who has gone missing. It is also revealed in the anime 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.

Izaya arrives at Raira Academy and saves Mikado from some bullies. Immediately after that, he and Celty follow Mikado home with the intent on locating a mysterious girl whom 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 while 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 phone number, in order to call her and make a 'deal'.

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 Kyouhei Kadota, whom he calls Dotachin, over. Although Kyouhei 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 "dara dara", a term meaning 'to do nothing'.

Izaya then speaks with Mikado. The info broker is surprised at the turn out of the Dollars first ever group 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 and that he would have to move to more underground activities to stay interested, but would soon get bored of that, too. 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", revealing himself to him as "Kanra."

At his apartment, Izaya meets with Namie. 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 Dullahans 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 would never suspect it to be in the hands of the organization she is a part of.

Saika Arc
Izaya plays a relatively minor role in this arc. He is interviewed by Shuuji about Shizuo, and since he doesn't want to talk about Shizuo, he refers him to Celty instead. Later, 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. He later reveals to Namie that he was the one who sent Takashi to Anri's house that night and that Takashi took the money he laid out on the table as bait for Celty and that he intended to use him to blackmail Haruna before Anri intervened, admitting the real slasher making an appearance had been out of his calculations.

Yellow Scarves 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, Higa, as a mole to report to him as the situation continued to worsen but it is revealed that Higa 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 upper hand 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, Izaya is 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 to Namie that Horada had somehow obtained Mikado's identity as the Dollar's founder, despite never giving him the info. He correctly identifies it as her doing and expresses joy at so many unexpected developments in his plan, despite its apparent failure.

Hollywood Arc
Due to the media uproar surrounding Celty and the bounty placed on her head, he tells her to stay away from his office. On his sisters' first day of school, Namie brings them up, and he explains their personalities. At some point, he discovers that Namie has invited them to the online chat room. In the chat room, he informs the others of a 10 million yen reward that was put out for Celty by Jinnai Yodogiri and Max Sandshelt.

After the city-wide motorcycle chase comes to a close, Izaya contacts Shinichi Tsukumoya to fill him in on everything that transpired and is upset by the fact that so much happened without his involvement. Shortly after, Shinra and Celty host a hotpot party and invite all their friends, including Shizuo, Mairu, and Kururi, but neglect to invite him. He asks Namie if she wants to have a hotpot party with him, but she only brushes him off.

Toramaru Arc
Due to the events of the Hollywood Arc leaving him behind, Izaya instigates the events of the Toramaru Arc in petty revenge. He first manipulates Akane Awakusu into attacking Shizuo and waits for Shizuo's arrival, leaving a crudely written moving notice with a new address on his door. When Shizuo arrives at the address, he finds several mutilated corpses strewn around one room in the office. The room is revealed to be one of the many offices of the Awakusu-Kai, and the Awakusu 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 Jinnai Yodogiri. While Kida is out of the city (and away from the chatroom) he hacks into Masaomi's account and impersonates him on the chatroom to manipulate Mikado similar to how he manipulated Masaomi during the Yellow Scarves incident.

Dollars and Blue Squares Arc
He sends out a post, suggesting Dollars members kidnap No and her friends to get revenge on Chikage. 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 Yodogiri 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 Jinnai Yodogiri 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. Yodogiri leaves Izaya bleeding on the sidewalk as he walks away. Izaya tries to call Namie but passes out before he can reach his phone.

Daily Life 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 named Manami Mamiya who he doesn't recognize. Manami with a knife in her hand states that Izaya tricked her into "dying" with him several months ago 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. Despite being severely injured, Izaya still overpowers her and successfully evades her attack, causing her to slash open the pillow under his head. Izaya is initially perplexed but soon starts laughing hysterically, recovering from his state of disillusionment. He thanks Manami repeatedly for "exceeding his expectations", 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. With his love for humans being revitalized, Izaya disappears from the hospital room along with Manami to proceed to his next plan.

Adabashi Arc
Izaya isn't really seen much in this Arc other than near the end. Namie mocks Izaya as she watches him converse with himself in the chatroom by using two accounts (Nakura on his left and Chrome on his right). Izaya notices her watching him and states that she must think it's strange of him to talk to himself. He explains that by doing this, he could easily manipulate another's opinion of him. Namie gives back some sarcastic comments regarding his lack of sociability, pointing out he is just a loner with no friends. Izaya laughs and asks her if she did not consider 'everyone else' in his apartment his friend, revealing a group of people he had gathered. A collective of grudges for various reasons against the Dollars.

These people include: Izaya also officially leaves the chat room as Kanra and takes up a new alias in the form of Chrome.
 * Namie Yagiri
 * Ran Izumii: the former leader of the Blue Squares. He states that he is only there to kill Kyouhei 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.
 * 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 high school and was responsible for jump starting 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 Yodogiri decides he wants to finish Izaya off. They're basically henchmen.

Dragon Zombie Arc
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 is dropped off by Shiki at Rakuei Gym. Aware it is an attempt to see if Akane recognizes Izaya and if he is the person to convince Akane to run from home, Izaya manages to feign innocence and walk away without trouble. Soon after he is attacked by his sister Mairu and Eijirou but manages to slip away when Mikage intervenes. Later that night, he messages Celty to ask her for a favor. Izaya tasks 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." 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."

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 the real Izaya. 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 Mikage Sharaku 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 and calls Nakura, informing him he had nearly become a target of the Awakusu-kai. It is soon revealed that the two of them founded Amphisbaena in their senior year of high school, which was an extension of the baseball betting club they created in middle school. On top of this, they had also created an underground club for legal drugs after they had graduated from college. Izaya goes on to explain how Earthworm had taken over Amphisbaena and greatly expanded its gambling operations in Awakusu-kai territory. Not only this, but Shijima had taken over their legal drug club, which became Heaven's Slave, and started manufacturing illegal drugs. Nakura is horrified to hear Earthworm and Shijima were doing these things in his name, but Izaya assures him there is no need to worry—even if things do take a turn for the worse, Shinra can always change Nakura's face again.

Some time later, as he heads home, Izaya 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 feelings towards Shinra, who may be the only person Izaya actually considers a friend. In his flashback of that middle school incident, where Shinra laid on the floor bleeding, what Izaya had felt was envy and defeat. Shinra was so blasé about his own injury and towards all humans in general, it was like he was the one "observing humans from afar." Izaya also realizes that, due to his plans to involve Celty in an all out war, Shinra might end up cutting all ties with him 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.

Kadota's 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.

A few days later, 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 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. After conversing briefly with Mikage and Kine, Izaya leaves the office, saying he has something to do at the hospital.

In an extremely rare case of self doubt and prompted by Kine to check himself in for taking a blow to the head, 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.

While there, Izaya decides to see Kyouhei 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. Unable to visit Kyouhei and accepting defeat at the hand's of Erika, 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.

Final Curtain Arc
Izaya makes the decision 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 crane 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 with hopes of dropping the steel beams on top of Shizuo. However, Vorona notices this and manages to push Shizuo out of the way, allowing the steel beams to fall on her instead. Annoyed, Izaya pulls out a sharpened piece of pipe before throwing 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 manner before hanging up and going in search of Izaya.

The fight begins, Izaya had set 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, after reaffirming his need to destroy Shizuo, throws a lit match into the room causing a large fire. Celty’s shadow appears soon after, descending down from the sky and dousing the fire. As the smoke clears, Izaya becomes aware that Shizuo has punched a hole in the floor to escape. Soon after realizing this, the unfinished building Izaya had been observing from; begins to wobble. At the base of the building, Shizuo had taken control of one of the steal beams, shaking it violently until Izaya loses his balance and falls. Picking up a steel beam, Shizuo smacks it into Izaya who only just barely managed to let the beam hit him feet first. The force of the impact sends Izaya crashing through a nearby office building. The force of the impact causes vast amounts of internal damage as well as damage to Izaya's spine. However, it's due to the adrenaline that Izaya continues on despite vomiting blood. When he regains consciousness; an injured Izaya slowly escapes the building. Shizuo, after entering the building in search of Izaya, spots the blood splatter on the ground before seeing Izaya out the window of the building attempting to escape. Jumping out of the window despite being many floors up, Shizuo continues the chase. Shizuo chases Izaya back into the city. Izaya had planned all along to lead Shizuo into a highly populated area, wanting everyone to witness the monster in action. Whether they witness Izaya slaying the monster, or the monster doing just what monsters do, killing. The crowd composed of Dollars, Toramaru, and Saika children, steer clear of the two. 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, before 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, only to have a knife thrown at him by Vorona, which buries itself in his side. Vorona is about to shoot and kill Izaya in Shizuo’s stead, because she’s already a killer, she’s already a beast, and Shizuo is not. However, Vorona's attempt to kill Izaya is thwarted as a flash grenade goes off - thrown by Simon.

Izaya is rescued by Manami and Kine who took advantage of the flash bomb to collect him and escape. Due to ongoing events involving Celty, Izaya's stab wound is sealed by her shadows in an attempt to 'fix' all the trouble she has caused by existing among humans. He wakes up in a car being driven by Kine with Manami in the backseat. Kine wants to take Izaya to Shinra, yet the informant requests to leave the city even if he won't survive the journey. Izaya's fate is left unknown at this point.

Durarara!! SH
It has been two years since the final fight between Izaya and Shizuo, however, Izaya has gone missing from the city. Many speculate he is killed by Shizuo or by Vorona, though no one knows for certain about his condition and whereabouts, including his family.

Izaya Orihara Spin-Off Series
Izaya has mostly healed from the wounds he'd incurred in his last fight with Shizuo, but he cannot walk correctly and his arms are still weak and cause him pain. He needs a wheelchair to move around, though his inability to walk is psychosomatic and he could run around like he used to if he would go to therapy. Even so, Izaya is apparently not willing to do anything about it; he claims he accepts his condition as a punishment for his refusal to accept the human parts of Shizuo. Izaya also considers it a punishment for the impure way he would show his love for humans. It's heavily insinuated that Izaya was traumatized by his fight with Shizuo.

Seemingly continuing his work as an informant, Izaya is seen in the prologue talking on the phone to a salaryman who intends to murder his co-worker for monopolizing the company they are supposed to share equal ownership of. Izaya has helped back him on this, providing him with the information that helped push him to his decision. It's only after the salaryman commits the murder, that Izaya calls him to explain that his co-worker only left him out of the company because he had gotten it into some illegal activities and didn't want the salaryman to be held responsible. Izaya goes on to taunt the salaryman a bit, calling the murderous path he chose 'very human' before hanging up and throwing away the phone.

Following this, Izaya decides that it's no longer safe to remain where he is staying, and thus disposes the cell phone he used to contact the salary man and packs up before relocating to another area. Some time after this event, he seemingly hears of what befell the salaryman's family and the family of the man he killed, and takes the children of both families, Haruto and Himari, under his wing. At an unidentified period of time, Izaya is called up by Densuke Sozoro and accepts to help prove his innocence and save his family from prosecution. In exchange, he has Sozoro work for him as his bodyguard for the next ten years.

A year later, Izaya is shown living in a hut on the side of a mountain somewhere in the Kanto region, though after reading the news article of the murder of Ryuuichi Adamura, he decides to accept Kakinuma's job request and moves into a royal suite in one of the nicest hotels in Bunokura. It's from this hotel room that he continues carrying out his hobby.

After bribing a local corrupt detective, Sasazaki, to ignore everything he does around the town, Izaya begins spreading rumors and gossip about one of the local families. He makes connections for information by approaching key people, including one of the new maids for the Adamura family. Sasazaki also feeds Izaya information for money. Local groups, police, and gangs around town quickly learn of Izaya's name, though the peculiar spelling makes it difficult for anybody to get information on him. It's due to Izaya's interference that the Adamura mine is exposed as being dried up, causing the subsequent vanishing of the family.

Various prologues intermingle the chapters in which various inhabitants of Ikebukuro are interviewed about Izaya. Shinra warns that Izaya is dangerous, but genuine in his love and that he doesn't mean any harm in his chosen way of 'loving' people. Shiki on the other hand, calls Izaya a child with too much power and asks the interviewer to tell Izaya that he is willing to overlook everything Izaya has done, but that he needed to stay out of Ikebukuro.