Ryuugamine Teijin, a young man who yearns for city life, was invited by his good friend Kida Masaomi to leave his hometown and come to Tokyo. Afterwards, Teijin entered the Kurara Gakuen in Ikebukuro, Tokyo. Masaomi told him that there are several people in Ikebukuro who must not be provoked, especially the aggressive gangster Heiwajima Shizuo and Orihara Izaya who runs an intelligence house. Masaomi also told him that there is a strange organization system in Ikebukuro, whose true identity is unknown, and it is only known that this street violence organization is called "Dollars". However, he did not expect that on the first day of going to Tokyo, Teijin, who was uneasy because of Masaomi's words, witnessed the urban legend "Headless Horseman" riding a black motorcycle through the streets...