5 most heartless anime gangsters (& 5 with a true heart of gold)

Anime gangsters walk on a fine line between ruthlessness and redemption. Some can be cold-blooded villains driven by ambition, power, or a distorted sense of justice. Standing firm and unyielding, they prove to be very strong figures in their stories. Of course, not all anime gangsters are made of stone.

Some characters, despite their affiliation with crime, exhibit genuine kindness. They display a layer of care and selflessness beneath their tough exterior. These complex individuals sometimes defy the usual stereotype of a gangster. Here are the five most heartless anime gangsters and the five with a true heart of gold.

Disclaimer: This list is ranked in no particular order and contains the writer's opinion and spoilers. Readers' discretion is advised.

Balalaika, Nero Vanetti, and other most heartless anime gangsters

1) Diavolo (JoJo's Bizarre Adventure: Vento Aureo)

Diavolo as seen in the anime (Image via David Production)

Diavolo is a character from JoJo's Bizarre Adventure: Vento Aureo who epitomizes the heartless nature of anime gangsters. He is the maniacal boss of the Passione gang with an unstoppable desire to rule and be in control. Diavolo displays his coldness by being willing to kill anyone who stands in the way of his rule, including his allies.

His Stand, King Crimson, has the power of erasing time, symbolizing his manipulative and cruel nature. Diavolo's complete inability to show empathy and his lust to retain his position of absolute power make him one of the most heartless anime gangsters.

2) Nero Vanetti (91 Days)

Nero Vanetti as seen in the anime (Image via Studio Shuka)

As one of the main members of the Vanetti family, Nero Vanetti embodies ruthlessness and cunningness that drives his every move. He is willing to go beyond the value of human life for the sake of power and control. Some of Nero's important decisions are brutal and show his calculated cruelty.

He is driven by the desire to maintain control over his family, never allowing personal relationships or moral constraints to hinder his potential success. His willingness to sacrifice and betray people makes him a heartless anime gangster.

3) Balalaika (Black Lagoon)

Balalaika as seen in the anime (Image via Studio Madhouse)

Due to her personality and calculated slyness, Balalaika from Black Lagoon is considered a heartless anime gangster. She is the leader of the Russian mafia group Hotel Moscow, in which she conducts business without any regard for human life. Balalaika's strategic mind and unflinching approach to violence make her a formidable figure in the criminal underworld.

She orchestrated savage attacks and manipulated her allies and enemies, establishing herself as one of the most ruthless anime gangsters.

4) Tetta Kisaki (Tokyo Revengers)

Tetta Kisaki as seen in the anime (Image via LIDENFILMS)

Tetta Kisaki from Tokyo Revengers is the very personification of heartless manipulation. Kisaki orchestrates brutal acts of violence and betrayal to fulfill his goals without remorse.

He further demonstrates a lack of empathy by being willing to sacrifice others for personal gain. His actions, driven solely by the thirst for power and control, cement his status as a heartless anime gangster.

5) Scythe Master (Phantom: Requiem for the Phantom)

Scythe Master as seen in the anime (Image via Bee Train)

Scythe Master from Phantom: Requiem for the Phantom is considered a heartless anime gangster because of his unforgiving and manipulative nature. He is a sadistic genius and the creator of Ein and Zwei.

His relationship with Ein is twisted as he shows false affection and uses her for his gain. Scythe Master values loyalty based on self-interest, prioritizing power and control.

Taro Sakamoto, Tatsu, and other anime gangsters with a true heart of gold

1) Worick Arcangelo (Gangsta.)

Worick Arcangelo as seen in the anime (Image via Manglobe)

Contrary to his tough exterior, Worick Arcangelo from Gangsta. is an anime gangster with a heart of gold. Several moments throughout the series portray Worick as protective of his friends and allies. He is extremely loyal and can be compassionate towards his partner and best friend Nicholas Brown.

Worick's concern extends to marginalized individuals and those who are suffering, reflecting a deep sense of justice and empathy. Though rather violent, his actions have motivations of protection and care for those he holds dear to him. This brings into view a rather soft-hearted person behind the tough personality.

2) Tatsu (The Way Of The Househusband)

Tatsu as seen in the anime (Image via Netflix)

Once an intimidating yakuza leader called the "Immortal Dragon," Tatsu abandons his criminal life for the quiet role of a househusband. Behind the rough exterior, he is a kind and caring husband towards Miku.

Despite his criminal past, Tatsu approaches everyday tasks with seriousness and attention to detail, reflecting his deep love and regard for his family. His transition from a wicked gangster to a caring husband makes him one of the most memorable anime gangsters.

3) Taro Sakamoto (Sakamoto Days)

Taro Sakamoto as seen in the anime (Image via Netflix)

Despite having a terrifying history as an unsparing assassin, Sakamoto's character is marked by his firm commitment to protecting those he values the most. His decision to retire from his violent career to lead a life with his family shows his affection for those close to him

Set against the background of his prowess on the battlefield, Sakamoto's tender and delicate nature mirrors his inner warmth, making Sakamoto an anime gangster with a pure heart.

4) Dazai Osamu (Bungo Stray Dogs)

Dazai Osamu as seen in the anime (Image via Studio Bones)

Dazai Osamu from Bungo Stray Dogs is an anime gangster with a heart of gold despite his outwardly aloof and cynical demeanor. Though he projects a traumatic and violent past, coupled with the unsavory reputation of being a violent member of the Port Mafia, he does possesses a deeper and caring side. Dazai always endeavors to protect those around him and frequently endangers himself to ensure their safety.

His personality is complex, shaped by an interest in helping and understanding people despite a background of criminal involvement. He possesses great inner goodness and is committed to making up for his past actions.

5) Ash Lynx (Banana Fish)

Ash Lynx as seen in the anime (Image via MAPPA)

Running a criminal organization in New York, Ash Lynx is compelled to protect his loved ones and seek vengeance for his traumatic past. His compassion is evident in his protective instincts towards his friends, often going to great lengths to protect those who mean a lot to him.

Ash's ruthlessness is a camouflage for his sweet and responsible persona. Notably, in the past, he possessed an intrinsic morality that conflicted with his criminal actions.

Final thoughts

Anime gangsters like Diavolo and Balalaika show cold-hearted ruthlessness. Their ambition for power and control drives their relentlessness and leaves no room for mercy, making them heartless anime characters.

On the other hand, characters like Tatsu and Ash Lynx show their softer sides, proving to be caring and loyal individuals despite their criminal backgrounds. These gangsters demonstrate the varying and complex portrayal of crime that anime offers.

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Edited by Rachith Rao