Kida is the audience’s tour guide to Ikebukuro, guiding Mikado around the strange jungle that is this wild city. He’s the cool ‘best friend’ character and always seemed to be comfortable amongst the dangers surrounding them, taking the initiative to introduce Mikado to the important figures across Ikebukuro. However, it was soon revealed that Kida was far more than just a tour guide and ended up becoming a part of this odd proxy gang war against his best friend.

Masaomi Kida is a character that we’ve seen every side of. His ability to learn from his mistakes and take a step in the right direction is admirable. Entering back into the series in DurararaX2, he’s humble and prepared to face the realities of life and the consequences of his actions. And there’s nothing cooler than doing the right thing, right? ...Right?

The Blue Squares were always a fairly vague gang and within the first season, they existed as little more than flavour text as the gang that the Yellow Scarves defeated. Whilst the gang was disbanded, their name was important and it’s one that stuck with us throughout the conflicts between the Dollars and the Yellow Scarves. But jump ahead to DurararaX2 and the Blue Squares are back in a brand new form.

Aoba is the original founder of the Blue Squares and ended up losing the group due to the gang war predating the first episode. But now that he’s back in town, he’s out to rebuild the Blue Squares using any means necessary. It’s a really cool progression and the conflicts between him and Mikado end up building them both as characters in this strange mutually advantageous relationship.

Everybody loves the underdog. There’s something brilliant about watching all of these powerful people galavanting around town, only to realise that our weak protagonist is perhaps the most powerful of all of them. Mikado’s place within Durarara shows a disconnect between strength and power, finally introducing the scope of community influence.

The Dollars is an online chat group that Ryuugamine formed as a joke. Anyone can join the chat group as long as they were invited. At its core, it’s just a chat group much like what you’d have on Skype. However, the invite-only nature and quick expansion of it eventually led to gangsters using the name “Dollars”. It was at this point that Mikado decided to turn it around and use the group for good, eventually creating the most powerful gang in Ikebukuro.

Speaking of the Dollars, Kyohei is one such member and the leader of his own gang who try to carry out good deeds throughout the city, even if it does involve terrifying means. Among a group of eccentrics, Kyohei’s ability to stay level-headed and collected is certainly valuable. He’s regarded as one of the more charismatic characters within a show, displayed through his own honesty, acting as a direct anti-thesis to Izaya.

In a town where the dynamic can change quickly and anger takes over logic, Kyohei is the one consistent force that pulls us back to reality and finds his own reasons for fighting, separate from the constant manipulation that’s consistent with other major characters in the show.

When a new season of one your favourite shows comes back after such a long absence, it’s natural to expect a gift. Something extra that doesn’t just say “I’m back!” It says, “I’m back and I’m better than ever!” The Orihara twins are that gift. As the sisters of the ultimate manipulative force that is Izaya, they’re just as eccentric. Together, they’ve manipulated their own personalities into polar opposites of each other in an attempt to make up for each other’s weaknesses at every turn.

It was even mentioned by Izaya that they flipped a coin to decide who gets which personality. Everything about them is so flippant and their extreme reactions to everything and vague loyalty is a strange mix between cool and creepy. Thank god there’s a screen separating us or the Orihara Twins would be the source of my nightmares.

Most wouldn’t regard a character who seems to play the role of comic relief so often to be “cool”. However, Shinra is far far more than just a set of jokes and plays an integral role within every plot point. Despite him being an underground doctor, he’s also very good friends with both Izaya and Shizuo, two of the most powerful forces within the city. He recognises both of their flaws and as a middleman ends up becoming tied up in the largest amount of occurring narratives out of any character.

The fact that someone who’s physically weak, not particularly manipulative and not really malicious can become such an important character within every conflict is just brilliant and he defies all our expectations of him. Most characters in his position would be constantly fearful of attack, but Shinra always remains calm, collected and ready to dish out a joke, even at the expense of some of the most dangerous people.

Shizuo’s possibly the easiest pick within this list. Inhuman strength, sunglasses and a profession as a waiter all seem to build up to “You’ve just been served puns” as well as the ultimate image of ‘coolness’. With possibly one of the strangest backstories within the series, Shizuo has had superhuman strength from childhood. But without a superhuman body, every time he ended up using it, he’d end up hospitalized. Through years of strain and self-abuse, he finally gained the strength to be able to support his own superhuman outbursts.

However, that isn’t what’s cool about Shizuo. When we’re first introduced to him, it’s as a character to fear. Someone who will violently hunt down anyone who wrongs him. So what changes our perspective is how he’s built up later on as someone who doesn’t really like violence and gets annoyed at his own short temper. It’s just unfortunate that much of Ikebukuro don’t see it the same way.

Simon is a constant unknown force and throughout the entire first season of Durarara, we’re not even totally sure who he really is. We knew he owned a Russian Sushi place in Ikebukuro and was connected with various figures around town, but his real place within the world was unclear. The same goes for what exactly Russian sushi is. There’s this great scene in the first episode where Mikado is told that the three people he needed to avoid was Izaya, Shizuo and Simon.

However, as someone with no real apparent feuds, Simon is the odd man out within that equation. That is until we get the chance to see his incredible strength and later hear his backstory as a former Soviets Special Forces operative. He is the strongest man in Ikebukuro and even Izaya mused that in a fist-fight between him and Shizuo, Simon would come out on top.