Tired of his mundane life, Mikado Ryugamine decides to move to Ikebukuro, a district in Tokyo, when a friend invites him. With everything from invisible gangs to rumoured beings, Ikebukuro is full of connected mysteries where people's pasts intertwine with the present.
Mikado Ryugamine begins his new life living alone as a high school student, awed and mesmerized by the new world around him. As Masaomi shows Mikado around, he offers one stern warning: "If you want to live here peacefully, stay away from Shizuo Heiwajima, Izaya Orihara, and a mysterious colour gang known as the "Dollars".
There is excitement at the Entrance Ceremony at Raira Academy for starting a new life. Amidst all this is Rio Kamichika: a girl with a notably dark vibe following her. Soon, a "crack" will run through this otherwise normal world.
Masaomi Kida is out about town, with Mikado tagging along, feeling a bit confused. Shizuo Heiwajima and Tom Tanaka are around as well, collecting debts. Anri Sonohara searches for a friend who hasn't attended school since the first day. Mikado notices Anri being bullied in an alleyway. He goes to save her, but not before a voice calls out.
People throughout the city speak of an urban legend known as the "Headless Rider". A surprising number of people have personally witnessed it speeding down the streets on a jet-black motorbike with no license plate.
Mikado, Masaomi, and Anri enjoy some after-school time, while magazine writer Shuji Niekawa makes little progress in his search to find the Strongest in Ikebukuro. The Headless Rider confronts a shadowy being with two crimson eyes glowing in the darkness of the city's back alleys.
Several people go missing in the districts of Ikebukuro and Shibuya. However, those people will not be missed, as they are fugitives and illegal aliens. A group of illegal aliens living in an abandoned hotel fall victim to some young "man hunting" thugs with metal pipes and knives.
Shizuo Heiwajima, also known as "the strongest man in Ikebukuro", is a man who relishes that title. Though he carries with him a high esteem, something is amiss. Lately, he has been extremely short-tempered and does not know why. His senior partner, Tom Tanaka, occasionally tries to calm him down, and Celty often worries over him.
Celty, anxious and uneasy about being unable to find her head, gets into a quarrel with Shinra and runs away from home. While he waits patiently for her return, a certain individual visits him. Meanwhile, an exchange student named Shiri wanders the streets of Ikebukuro with a sign and sketchbook asking random people "Hello! What are you looking for?" As she gains more and more answers, we learn that the ideals of the people of Ikebukuro are very different.
Yagiri Pharmaceutical's executive director is irritated by the fact that she is unable to determine the whereabouts of her beloved younger brother Seiji. To locate him, she contacts Izaya Orihara, the information broker. Meanwhile, Seiji, unconcerned that he is wanted, continues to roam the streets of Ikebukuro with a woman with a scar on her neck.
Mikado had bumped into the girl with the scar on her neck on a street corner. Filled with a sense of dejavu, the sounds of a neighing horse reach his ears. The girl was being chased by the Headless Rider. Mikado succeeds in safely getting home with the girl, who tells him she has amnesia. A fearful Mikado consults with Masaomi on a course of action, and ultimately decides to wait and see what happens.
Anri's missing friend, the Dullahan, the girl with the scar on her neck, Yagiri Pharmaceuticals, the kidnappings, and the Dollars, little by little, the pieces begin to fall into place. On a busy street in Ikebukuro, amidst the hustle and bustle, Mikado confronts Namie. Although he is afraid, Mikado is focused and determined to reveal the truth.
Seiji attacks Mikado for the return of the girl with the scar on her neck. However, in the midst of the fight, the girl reveals the truth, which shocks both Seiji and Celty. Seiji is seemingly paralyzed by the shocking truth, while an infuriated Celty leaves the scene. Meanwhile, a shadowy figure, Izaya, approaches Mikado, a man who just earlier had watched these people be teased by fate.
Half a year has passed since the Dollars meeting and Ikebukuro seems to have returned to normal. But underground, the Yellow Scarves and the Slasher are becoming increasingly active. Darkness approaches, ready to destroy the days of peace, as each is forced to face their past and present.
Anri is attacked by the Slasher. The same night, the user Saika appears in the chatroom, and posts a puzzling message: "Today. Cut. Did cut. More. Stronger. Love. Wish. Wish. Is. Want." Mikado, worried about rumors that the Slashers are the Dollars, decides to cooperate with Celty.
Magazine Journalist Shuji Niekawa's unbridled passion is raging stronger than ever. After much thought he begins to investigate the supposedly strongest man in Ikebukuro: Shizuo Heiwajima. While walking around the town and talking to people, he is suddenly attacked!
Anri gets attacked by the Slasher, but Kyohei's gang witness the scene from their van and rescue her. Shizuo and Celty join the fight, and after defeating the Slasher, they finally reveal his true identity. However, this moment of relief doesn't last long as Celty is shocked to read what has been posted in the chatroom.
Haruna Niekawa chases Nasujima who, unexpectedly, appears at her house. Anri, who also happens to be there, follows. As she faces off against Haruna, who is controlling the gang of Slashers, truths about her past are revealed. Elsewhere, Shizuo fights an unending battle against the Slashers in South Ikebukuro Park. As he defeats them one after another, his expression starts to take on a hint of joy.
Civil unrest begins to descend upon the city of Ikebukuro. Amidst this chaos, Izaya grins happily as he observes everything going according to plan. Unaware of Izaya's plan, Masaomi finds himself in an abandoned building, depressed, thinking about his past: how he ended up back there and how a girl named Saki Mikajima still waits for him at a hospital. Izaya's words, "You can never run from your past", ring through his head.
It's another normal day for Mikado, Masaomi and Anri. But Anri notices that something is wrong with Masaomi, and takes action to find out what it is. Elsewhere, a gang-war breaks out between the Yellow Scarves and the Dollars over the identity of the Slasher. The standoff grows as Mikado's desire to stop it is ignored.
The Headless Rider, a member of the Dollars, saves someone with a katana. As a result, the Yellow Scarves became even more suspicious that the Slasher is also a member of the Dollars. After doing some investigating, Masaomi starts to suspect that the remnants of the Blue Squares, a gang that he once fought, have slipped into the Dollars. He decides to visit Kyohei's gang to learn the truth.
Masaomi's orders are ignored as the Yellow Scarves begin to hunt down members of the Dollars. Mikado becomes extremely depressed after seeing a friend of his get assaulted by the Yellow Scarves and begins to question whether the existence of the Dollars is worth such a sacrifice. Meanwhile, Anri tries to put a stop to the gang war, but ends up making the situation worse.
The Dollars are enraged at the evil deeds of the Yellow Scarves. While taking in the members' comments on the BBS, Mikado desperately tries to find a solution. Meanwhile, the Yellow Scarves learn that Anri is the girl who escaped from their hideout during the night of the meeting, and track her down. However, an unexpected group of people steps in to save her...
The sound of a gunshot resounds from a nighttime alley, followed by a phone call for Masaomi. Mikado goes out somewhere with Celty, followed by Anri who later learns the truth. Each of their hearts is filled with trust, doubt, and unease. Everything appears to be rushing toward a conclusion, and a smile crosses Izaya's face as he enjoys the chaos.
Filled with unwavering determination, Masaomi enters the abandoned factory, and encounters the unexpected. At last: Masaomi, Mikado, and Anri face off. As each of them carries within themselves inexpressible feelings, they eventually find an answer.
The Headless Rider receives a mysterious red bag that creates big trouble. The Yakuza chase a gangster, and a wagon disappears on the highway, pursued by suspicious men in black suits. Mikado and his friends should be enjoying the summer festival, but have been swept up in the events.
While on location shooting and hosting "Love Love Star Chance! Find Ikebukuro's Number One Couple!", Yuhei looks for a cute couple to star in his upcoming movie. Amongst the street audience gathered around for the show, Shizuo calmly keeps an eye on his brother, but things are about to get way out of hand as tempers flare and vending machines and signposts get flung when he finds out that Yuhei is being set up for a trap orchestrated by his archrival, Izaya Orihara!
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