DURARARA!!

Mikado Ryūgamine, a young boy who longs for the exciting life of the big city, moves to Ikebukuro, Japan at the invitation of his childhood friend Masaomi Kida, who he has not seen since he was young, to attend Raira Academy with him. After first meeting Masaomi at the train station, they both set out at night to the streets of Ikebukuro. Masaomi warns him about people he doesn't want to cross in the city: like a violent and superhumanly strong man, Shizuo Heiwajima, an information broker, Izaya Orihara, and a mysterious gang known as "The Dollars." After running into some of the side characters, Mikado witnesses a local legend called the "Black Rider", who rides around Ikebukuro on a black bike that occasionally brays like a horse, and who is also rumored to have no head under its helmet. The "Black Rider" is Celty Sturluson, an Irish dullahan who is in Ikebukuro looking for her stolen head. The narrative follows all of the characters equally, showing how their lives intersect, creating a greater plotline from what each character knows about a common incident.

Izaya Orihara (折原 臨也, Orihara Izaya^?)

Voiced by: Hiroshi Kamiya (Japanese), Johnny Yong Bosch (English)

Online Alias: "Kanra" (甘楽^?) and "Nakura"

Izaya is a young man who sells information for his own satisfaction and is behind the most relevant events in the series. He claims to love the entire human race, except for his arch-rival Shizuo Heiwajima, and exhibits said love by putting humans in often miserable conditions and observing their reactions. He is a master of parkour, and is also quite skilled with his flick-blade, as he is implied to be 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 the man noticing it. At the beginning of the series, Izaya suspects that Mikado is the creator of Dollars, which is proven correct later, and knows the identities of the leaders of the three main forces in Ikebukuro. Izaya, himself, is a member of Dollars and is responsible for recruiting members after Mikado stopped sending out invitations. Online, he pretends to be female, and talks in a feminine manner in the chatroom. His motives are not entirely clear, though one of his main goals is to create a gang war in Ikebukuro that will "wake up" Celty's sleeping head.

In the past, Izaya attended 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. In the novels, Izaya framed Shizuo for crimes on several occasions. In the anime he gives Shizuo constant problems, ranging from daily attacks by gangs to framing him for crimes. Izaya also has two younger sisters, Mairu and Kururi, who are twins and troublemakers.

His name comes from a combination of the biblical Isaiah and Japanese for "the one who looks over the crowd".

Shizuo Heiwajima (平和島 静雄, Heiwajima Shizuo^?)

Voiced by: Daisuke Ono (Japanese), Crispin Freeman (English)

A blond young man who is always seen wearing sunglasses and a bartender's suit. Although quiet and nondescript while not angered, he has a very short fuse and fights with incredible strength, though he claims he hates violence. Despite his simple and unrefined fighting skills, namely his use of road signs, trash cans, and vending machines as weapons, he is considered the strongest fighter in the series. In the novels his power is described as the naturally unlimited form of human strength and likened to "adrenaline power" that can give people superhuman strength in times of emergency. In addition, Shizuo is capable of often superhuman parkour moves, a skill he obtained naturally from years of hunting down Izaya Orihara. He is also a member of Dollars, although he left the group in Volume 6 after some members of the Dollars resorted to kidnapping to settle a dispute with a rival gang.

Shizuo works as a bodyguard for a debt collector in Ikebukuro and carries intense animosity towards Izaya. He has a younger brother, Kasuka, who is a top idol under the showbiz name of Yuuhei Hanejima. He is also a long-time acquaintance of Celty. Although he and Izaya Orihara are on bad terms, Shizuo is actually well-acquainted with Izaya's younger sisters, Mairu and Kururi.

His first and last name translates literally, and ironically, into "serene man" and "peaceful island" respectively.