Top 10 Fictional Mob Bosses

I know that there are probably better choices than some of my picks for this list.  The likes of Scarface’s Tony Montana and The Departed’s Frank Costello and The Soprano’s Tony Soprano are some of the noteworthy names that aren’t in this list.  There are just others, though less popular, that I found to be more enjoyable.  “Mob bosses”, for all purposes of this list, are characters that happen to be either actual heads of a crime organization or rightful heirs for the position – regardless of their alignment: good, bad, or in between.              

10.) JABBA THE HUTT

I don’t really care much for this ugly, sluggish alien, but I love Star Wars and he’s one of its important antagonists that I still think he’s qualified to get a spot in this list.   This despicable and powerful crime lord is depicted as greedy, ruthless, and derives pleasure from keeping slave girls, maintaining a gluttonous lifestyle, and watching others suffer a slow, terrifying death.   

  

9.) LIM ARYONG

 

I quite enjoy South Korea’s My Wife Is a Gangster and My Wife Is a Gangster 3 (didn’t see the second one).  The movies aren’t really connected but do share the same premise: a romantic comedy that features a badass female mob boss.  Between the two movies’ respective protagonists, I’d go for MWIaG 3’s Lim Aryong than MWIaG’s Eun-jin.  MWIaG 3 having a better story (for me) helps.  The whole language barrier that Lim Aryong had to undergo also added more dynamic to her character and provided more memorable, funnier character moments.  Actress Shu Qi dictated amazing strength, presence, and grace when portraying her character and executing her action scenes that I can’t help but be quite dazzled.    

     

8.) YAMAGUCHI “YANKUMI” KUMIKO

Though she’s a Yakuza Ojou (boss/princess), Yankumi is more excited to be a teacher.  She carefully keeps her identity secret from her students and co-teachers, and will only display her proficiency in combat whenever her students are in trouble. 

Yankumi is actually one of my most favorite female characters in fiction.  However, though her Yakuza background helps in making her an interesting character, she’s actually not much of a mob boss, so she’s not rated any higher.

7.) VICIOUS

Vicious is the main antagonist of Cowboy Bebop.  At first, he was a mere foot soldier for the Red Dragon syndicate, but he overthrew its leadership to become its boss.  If his rival, Spike, is a great gunslinger, he, on the other hand, is an incredible swordsman (though he didn’t make my list on fictional swordsmen).  He is merciless and ambitious, and won’t hesitate to kill whoever is on his way.  

    

6.) THE VENTRILOQUIST & SCARFACE

Oswald Cobblepot a.k.a. the Penguin is the more popular Batman-villain mob boss, but I find Arnold Wesker a.k.a. the Ventriloquist and his puppet/alter ego, Scarface, significantly more fascinating.  Suffering from schizophrenia and multiple personality disorder, the usual timid Wesker projects his sociopathic, cunning, and criminal personality to Scarface, his gangster puppet.  However, for Wesker, he delusionally considers himself as a mere docile minion who has no choice but to obey Scarface’s biddings.  The Ventriloquist/Scarface is definitely one of Batman’s most underrated and most unique villains.    

    

5.) TSUNAYOSHI SAWADA

Tsunayoshi Sawada, or Tsuna for short, is the main protagonist of the delightfully wacky mafia-themed manga/anime, Katekyo! Hitman Reborn.  Despite being just a junior high student, Tsuna found himself the rightful tenth boss of the most powerful mafia famiglia in the world, the Vongola Famiglia.  He is understandably unwilling to have anything to do with the mafia, but he is forced to embrace the role of the Vongola Tenth in order to protect his friends and the world.

Tsuna started off as cowardly, inept, and clumsy.  But with the guidance and training of his tutor, Reborn (a legendary hitman that has been mysteriously transformed into a baby), as well as the mafia conflicts that he’s thrown in because of his Vongola title, Tsuna is developed into becoming an accomplished mafia boss and a courageous, strong-willed individual. 

4.) THE KINGPIN

In the Marvel Universe, Wilson Fisk a.k.a. the Kingpin is considered to be the most powerful crime boss of New York City.  For most of Fisk’s character history, he is seen as a high-profile public figure whose criminal nature was known to all; however, he was so efficiently careful in making sure that none of his criminal enterprises could be traced to him that the law found it impossible to send him to prison (at the present, however, he’s no longer concerned in being subtle, and is even a wanted fugitive, after the Superior Spider-Man outed him).  His appearance is that of a “fat man”, but his bulk is actually mostly muscle instead of lard.  That’s why he’s not only a criminal mastermind but is also very dangerous to engage in physical combat.       

3.) BALALAIKA

In an anime such as Black Lagoon that is full of badass characters, I find Balalaika as the most awesomely badass.  Her real name is Sofiya Pavlovena but no one dares to utter it in her presence.  She is the boss of Hotel Moscow, the Russian mafia based on Roanapur (a fictional city found in southeast Thailand that serves as a criminal hub) and one of the regular clients of the Lagoon Company (the anime’s main protagonists, a merceneray/pirate/smuggling firm). 

A former Army captain of the elite Vozdushno-Desantnye Vojska (the Russian Airborne Troops), Balalaika proved to be a tough combatant and a brilliant strategist during the hellish Soviet War in Afghanistan, earning the deepest respect and fiercest loyalty of his troops.  When she became a mafia boss, these same soldiers became her subordinates and enforcers in Hotel Moscow.  Thus, being made up of former elite soldiers, Hotel Moscow operates with efficient military precision and discipline, making them the strongest and most successful crime organization in the region.    

2.) & 1.) MICHAEL & VITO CORLEONE

The Godfather and The Godfather Part II (I don’t hate the third installment as much as most, but I have to admit that it was significantly inferior) are not only two of the greatest movies of all time, but they also served as the ultimate depiction of mob culture (in fact, I read once that not only did its romanticized depiction shape our pop culture awareness of mob culture, but it also compelled real-life mobsters – who were merely barbaric thugs at that point – to imitate the stylishness and class portrayed in the films).  Thus, it’s not a surprise that the definitive mob bosses in fiction are the titular Godfathers – Vito Corleone and, his son and successor, Michael Corleone – and the holders of the top two spots in this list.

Both are smart, calculating, and intimidating dons.  Both are vengeful and ruthless when necessary.  Both love their family and value loyalty and respect greatly.  Both have strong charisma.  Both are awesome.  But Vito edges Michael a bit in my eyes.  Al Pacino’s portrayal of Michael was terrific, but Marlon Brando’s portrayal of Vito was incredibly magnetic.  Moreover, Vito’s character development during his younger years (as portrayed by Robert De Niro) was a bit more compelling.