Durarara!! (デュラララ!!), often shortened to DRRR!!, is a Japanese light novel series written by Ryohgo Narita, with illustrations by Suzuhito Yasuda, that has also been adapted into a Japanese anime series. Durarara!! tells the story of a dullahan working as an underworld courier in Ikebukuro, an internet-based anonymous gang called The Dollars, and the chaos that unfolds around the most dangerous people in Ikebukuro.
http://www.crunchyroll.com/durarara
Both Seasons 1 and 2 are on Crunchyroll if you're so inclined. (You'll probably need premium to keep up on X2, though.)
If you're at all familiar with the similarly excellent Baccano, this was done by the same animation team(and even includes cameos!), so rest assured, these guys can handle massive casts and chaotic, entwining plots.
The PlayersMikado Ryugamine
Technically the main character, though that's a technicality with an ensemble cast like this. An unassuming student caught up in the strange events of Ikebukuro all because a friend invited him to attend classes there.
Masaomi Kida
Mikado's best friend. Whimsical and flirtatious to a fault, but what does he know about the mysterious Yellow Scarves gang?
Anri Sonohara
Attends classes with Mikado and Masaomi. Very shy and withdrawn, though there's a whole other side to her in certain circles of Ikebukuro...
Izaya Orihara
A wandering psychopath who seems to know everyone and everything of note in Ikebukuro. Also the constant target of...
Shizuo Heiwajima
A bartender/peacekeeper who possesses superhuman strength and durability. He always tries to kill Izaya on sight(and always fails).
Celty Sturluson
A roaming Dullahan in search of her head, who now takes the form of a headless motorcyclist. Although she can't talk, she can certainly text... at 120 WPM.
Shinra Kishitana
A street doctor who took in Celty. They seem to be a perfect match, but is it love... or just science?
That's maybe half the cast of the show, but it does a good job of giving everyone equal time and development.
I just started Season 2, so I can't share much about it yet(apart from it being fantastic so far), so here's some incredible music from Season 1-2.
https://www.youtube.com/watch?v=RQOc_07raNEhttps://www.youtube.com/watch?v=KsdJFwpkyBw
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