Senkou no Night Raid (Night Raid 1931) documents the adventures of four intelligence agents from the Sakurai Kikan agency during the height of Imperial Japan’s occupation in China, specifically Shanghai during the early 1920s and onward. Surrounded in various schemes, mysteries and conspiracies encompassing the political and economic strife of this era, Senkou no Night Raid brings the scenario to a higher level of intrigue by providing the characters with special abilities to help solve the disturbances around them.

Of the four Sakurai intelligence agents, Kazura Iha appears to be the most eye-catching, both personally and by his ability. Kazura’s demeanor is very reserved and polished, due to his samurai heritage. He carries himself with confidence and demonstrates self-restraint using his ability on an “as-needed” basis. Moreover, his special supernatural ability is teleportation, freely moving from place to place, as long as he can envision where he lands. Lastly, he fits the bill for the persona of gangster in this time period.

Gangsta. is set in the city of Ergastalum, filled with mobsters, thieves, crooked police officers and vice crimes. Straddling the sides of criminals and enforcers are Nicolas Brown and Worick Arcangelo, also known as the “Handymen”, who handle the affairs of the opposing forces when they aren’t able to complete the tasks on their own. The story begins when Nicolas and Worick are assigned to and succeed in killing the local pimp. Alongside a prostitute also marked for death, Alex Benedetto, Gangsta. excitingly follows various events unfolding as Ergastalum undergoes a shift in power between “normals” and “twilights” and corruptible dominance.

From the “Handymen” duo, Nicolas steals the show. Nicolas is deaf, but this handicap does not hinder his other skills. He demonstrates his strength with his brazen attitude and unapproachable rough exterior. Nicolas’ threatening and frightening reputation is coupled with his swordsmanship and criminally violent tendencies.

Bungou Stray Dogs is an action, supernatural anime following Atsushi Nakajima, an orphan who gets recruited by the Special Detective Company. This group of detectives tackle seemingly impossible cases in addition to fending off their counterparts, the “Port Mafia.” Aside from their intellect and talents, these detectives have incredible abilities that are extremely helpful in violent and intense confrontations. Bungou Stray Dogs channels the development of each character and how they came to be, as well as countless, stirring mysteries to solve.

Akutagawa Ryuunosuke is the Port Mafia’s current leader. His appearance is gangling and ominous. His ability is the Rashomon, where his coat transforms into a shadowy beast and can be manipulated in various forms. Akutagawa is the most vicious member in the Port Mafia because he is notably opportunistic. Although he has a great appreciation for his gang, he has a clear-cut perception of retaining strong and powerful assets, disregarding elements that will drag him and the gang down.

91 Days is a drama thriller, emphasizing criminal activity and the overall livelihood of people during the prohibition era. Mob ties and revenge-seeking gangsters dominate the storyline. As 91 Days is still airing, this anime chronicles Angelo Lagusa, a young man whose family was murdered in his presence. By a narrow escape, we fast track seven years where Angelo is presented with a list of names of the gang members responsible for the murder of his family. Using his intellect and wit, Angelo integrates himself into the mafia world, cautiously waiting for the opportune moment to strike back at the people who took his family away.

After harboring such intense animosity and hatred for the Vanettis, the crime family responsible for the murder of his parents and brother, Angelo demonstrates the most painful and damaging way to retaliate: trust and then betrayal! Angelo makes the list for top 10 anime gangster character because of his malevolent intent portrayed by amazing action scenes. Frankly, he is one bad mofo.

Nisekoi (Nisekoi: False Love) is the story of Ichijou Raku, the son and heir to one of the Yakuza leadership. A decade ago, Ichijou was given a precious locket from a little girl, promising her that they would reunite in ten years time, open the locket and be together. Time has passed and Ichijou is now in high school. He meets Chitoge Kirisaki, the daughter of the boss from a rival gang. In order to keep peace between the two, the heads of the opposing gangs agree that Ichijou and Chitoge form a faux relationship. In this romantic comedy, Ichijou must learn to balance the clashing personality of Chitoge, in addition to discovering who this mystery girl is from his past.

Unlike the aforementioned gangster characters, who exhibit dark, scary, and bad boy appearances, Ichijou fits into this list because of his association with the famed organized crime group, the Yakuza. Furthermore, the operation and methods to maintain order between the two dueling gangs, although unpractical (e.g. dating rival gang members), may produce unlikely outcomes that can occur in other instances, furthering alternative objectives and strengthening gang status.

Gungrave follows BFFs Harry McDowell and Brandon Heat: two delinquents and members of the most renowned and powerful crime syndicate, Millennion. Having to earn the confidence and esteem of the Millennion hierarchy, the duo must complete tasks assigned by their superiors in order to advance through the chain. Based on the excitingly popular videogame, Gungrave depicts the inner-workings of gang structure and leadership, unveiling where loyalties, dishonesty, and treachery inhabit.

Between Brandon and Harry, Harry takes the cake on the debate of “who is more gangster”. Without spoiling too much, when it comes to wanting power, Harry is super thirsty for it; acting on his own accord for personal gain, double crossing members and various criminal partners, and basically doing whatever it takes. As it is commonly known, “power corrupts.”

Kenichi Shirahama is your average teenage boy, with an affinity for physically stimulating activities that do not require personal engagement from himself. Essentially, he is an observer more than a do-er. Nonetheless, Kenichi works up the courage to join the school’s karate club. With many members of the club against him being apart of the “team”, Kenichi is somehow forced to fight one of its members in order to prove his worth. At a loss as to how he will accomplish this challenge, he runs into a new classmate, Miu Kurinji, who herself is a skillful fighter. As Kenichi trains for the task to come, joined by Miu and many skillful masters of their respective class, who all reside at the dojo she trains, Kenichi learns and develops his own personal style of fighting.

As Kenichi does not identify with your typical gangster persona, he is acceptable on this list for top 10 anime gangster characters because of the multitude of ass-kicking styles he acquires in a short amount of time. Harnessed in that average boy body awaits a serious beating if someone strokes Kenichi the wrong way! Additionally, as Kenichi learns these various disciplines, his confidence and physical toughness increase, as well as they should because he is faced with fighting Ragnarök, the strongest gang in his neighborhood. Kenichi’s rivals of Ragnarök, also known as the Eight Fists, are the embodiment of notable figures of Norse mythology, e.g., Loki, Hermit and Valkyrie, who can easily defeat fifty opponents or more. Furthermore, the members of Ragnarök are not just average thugs and hoodlums, but are extremely skilled fighters who, eventually are defeated by Kenichi.

Katekyo Hitman Reborn! is a mafia-centric anime that isn’t quite mafia because it is also combined with supernatural themes and adorable miniature characters. Tsunayoshi “Tsuna” Sawada is an incredibly awkward and scrawny guy who happens to get thrown into the mafia world due to his succession in leadership within the notorious Vongola family. In preparation for his new duty as the tenth boss, he is bestowed a home tutor, Reborn. Reborn is one of the miniature beings in this anime who demonstrates the ways of a professional hit man. From this point forth, Tsuna’s life drastically changes, as he faces the obstacle of what is required in the family business.

Tsuna is on the list for top 10 anime gangster characters because of his forced affiliation to his mafia family. Although he tries so hard to stay away from this path, the importance of the Vongola family to stay in power is not a decision that can be ignored lightly. In becoming the tenth boss, the customs and legacy that have been retained for decades are on the brink of dissolution. Therefore, a major trait of the mafia revolves around upholding tradition and loyalty to the family. “Blood is thicker than water.” As Tsuna combats various challengers, his strength and abilities progress in line with the development of this anime.

Mikado Ryuugamine moves to the big city, Ikebukuro, after hearing of its excitement and to attend school there. His childhood friend, Masaomi Kida, becomes his tour guide, showing him all the cool sights. Together, they explore the city with various run-ins with a myriad of characters. These characters are highlighted throughout the anime, notating their own trials and tribulations that result in a massive spider web of interconnectedness. Durarara! is a captivating and intriguing series, leaving viewers eager for what’s to come and how everything comes full circle.

Izaya Orihara is a devious and manipulative character that has a way of acquiring Intel around Ikebukuro. He is very sneaky and resourceful. Izaya loves to stir trouble and chaos wherever he goes, particularly with Shizuo, the strongest guy in Ikebukuro. He is very savvy when it comes to staying out of trouble himself. More often than not, he sees his share of conflict, where he can easily maneuver and outwit his opponents. Izaya, in this view is dangerous.

The story of Baccano! expands throughout a significant time range, from 1711 and 1932, focusing on a variety of characters and sequences of events, who are all connected to each other. Baccano! is filled with intricate scenarios that are threaded together to form an extremely exciting and lively anime. Without spoiling too much, the major themes in Baccano! include an elixir of immortality, feuding mafia groups, a rampaging killer, and a duo of “Bonnie and Clyde” bandits. As there is no main focal story and each character has their own personal experiences to tell, Baccano!’s non-linear fashion of conveying experiences is very unlike traditional anime, but nonetheless super stimulating.

Ladd Russo is a maniacal, reckless, and sadistic hit man, obsessed with violence and inflicting harm to victims he deems “too safe”. He is a confident fellow with an extremely active personality, doing everything with style. He enjoys what he does, a little too much, and to the highest degree, is really good at it. Ladd’s background is traced to mob affiliation because of the Russo Family being a major criminal syndicate in Chicago, during the twentieth century. Although he is not as gifted as the other Russo family members, Ladd nonetheless operated in the family business.

We discover that the root cause to the way Ladd currently operates is due to the tragedy that occurred when he was a young man. He was captivated and in love with a vivacious young lady named Layla. The two were going to elope, but she unfortunately was killed and it somehow was linked to Ladd. This event impacted him greatly, emotionally and psychologically. Later on, we do observe Ladd’s softer side, especially when it comes to his lover, Lua. Ladd values her companionship equally if not more than his own self. Conclusively, Ladd is the number 1 pick for our top 10 anime gangster characters because of his connection to the mafia, his motives to act in such reckless violence, his sway and confidence, and his menacing nature.