Izaya Orihara

Izaya Orihara is an underground information broker on the Ikebukuro III. His virtual persona on the Ikebukuro's chatroom is a teenage girl named "Kanra", which he uses to gather information on other residents.

Appearance
Izaya is a handsome man of Japanese descent. He wears a distinctive black coat with a large fur collar that reaches down to his hips, as well as a plain black long-sleeved v-neck, pants and dark brown shoes.

Personality
Izaya is extremely cunning and manipulative and aims to know everything about everyone, even to the point where he will pretend to be a teenage girl online in order to get closer to other residents of the Ikebukuro III. He delights in playing games with the Ikebukuro's residents and seeing how they react to stressful situations, especially ones that he orchestrates. He owns a chessboard in his apartment which he uses to represent the Ikebukuro III, with the chess pieces representing some of the residents that he has taken an interest in. The reason for his obsession, if there even is one, is unknown. He also exhibits other strange tendencies, like gloating about his schemes to himself when nobody else is online.

He is also extremely agile and has truly impressive reaction times: He was able to easily dodge a bullet fired by Hesta at point-blank range and use the environment to his advantage in order to escape.

Kanra Logs On
Izaya's first appearance was under his screen name, Kanra, in the Ikebukuro III's chatroom. He logged on to discuss the strange ship (belonging to Marahh Ictis and co.) that had landed in the Ikebukuro III's dock, jokingly saying that he hopes they're not there to cause trouble. Later that day, he talked to Saika, who mentioned that she had a problem that she didn't want to drag Kanra into, but Kanra began pestering her about it, causing her to log off. Because he had the chatroom to himself, Kanra started gloating about the fact that she had no idea how much he already knew.

The next time he logged on, Kanra stumbled upon a conversation between MoodyBlues14 and Pure_Water_100% regarding a girl that Masaomi Kida was hanging out with. Kanra told them that he thought her name was Anri Sonohara, but that he wasn't sure. Kanra then mockingly called them perverts, causing a small argument to break out, after which the other two logged off. He gloated to himself again and logged off to go and meet Hesta.

Encounter with Hesta
Izaya was hired by Hesta to dig up information on the mysterious killer terrorizing the Ikebukuro III. He managed to discover that some documents relating to the killer's sword had fallen into the possession of some local thugs, so he tracked them down and paid them 2000 credits for the documents, intending to recuperate his losses from his client later.

He soon met Hesta in a shady back alley to show her what he had found. As soon as he was given the initial agreed-upon payment of 500 credits, he showed Hesta some of the documents and explained a bit about how the sword worked. Hesta refused to believe that the sword was supernatural in nature, and was enraged even further when Izaya told her that he was withholding the rest of the information until she gave him the additional 1500 credits that he had to pay for the documents. When she pulled out a gun and fired at him, Izaya used his parkour skills to climb up a nearby building and escape across the rooftops.

Back at his apartment, Izaya accessed a video recording of what happened in the alley in order to determine more about Hesta's identity. He lamented the fact that he forgot to ask her name when they first met, but reassured himself with the thought that he would have plenty of opportunities to learn more about her.

New Strings
It wasn't long before Izaya uncovered a video of Anri's encounter with Kuu and Marahh. He moved the chess piece representing her to another position on his chessboard to reflect the unexpected turn of events.

Later, Izaya was confronted in the street by Masaomi Kida, who demanded to know why he was following him and his friends. Izaya replied that he just wanted to make sure they didn't get into trouble, especially Anri, who he will be keeping company. Enraged that he would threaten his friend, Kida lashed out at Izaya, but Izaya sidestepped the attack and escaped by climbing onto the rooftops like before.

Some time later, Izaya met Anri, just as he had threatened. He followed her to her apartment, and when he saw her drop her keys, he picked them up and gave them back to her before walking away.

As Kanra

 * Saika: Kanra and Saika have a friendly relationship due to being the only two "girls" who frequent the chatroom. When Kanra disappeared without warning (because he went to meet Hesta), Saika was worried about "her", hoping that "she" wasn't in any trouble.
 * MoodyBlues14: Kanra and MoodyBlues know each other well due to being frequent visitors of the same chatroom. Their relationship is generally a pleasant one, but MoodyBlues is sometimes frustrated by Kanra due to "her" tendency to turn the topic's subject back around on whoever wants to discuss it, for example, Anri Sonohara. MoodyBlues pointed this out to Kanra, telling "her" that this behavior is why nobody wants to come and meet "her" in real life, but Kanra just laughed it off.
 * Pure_Water_100%: Pure_Water_100% seems to be reluctant to talk to Kanra, always logging off shortly after "she" joins the chatroom. Kanra speculated that this is because he is intimidated by "her", but Pure_Water_100% later implied that it is because "she" had grieved him in some way.

As Izaya

 * Hesta: Izaya has made an enemy of Hesta due to the way their meeting went: Izaya spoke to her in a mocking tone, and demanded that she pay extra for some of the information he obtained. He managed to piss her off so much that she even fired a gun at him, but he escaped intact.
 * Masaomi Kida: Kida is no friend of Izaya. He angrily confronted the spy in the street when he found out that he was following him. When Izaya threatened Kida's friend, Anri Sonohara, while neglecting to explain himself, Kida lashed out at him, but Izaya dodged the attack and scurried off.