The mob/crime boss is one of those indelible villains that has populated countless films and TV shows since the earliest days of film.  A good villain can’t just be purely monstrous, there has to be something charismatic that makes them interesting. The mob boss character tends to fall into a rather narrow image: nearly always male, middle-aged, dark hair, intense stare, outwardly cool, but prone to explosive rage and acts of brutality. Traditionally, mob bosses in the movies were Italian and from the mafia, but then came the Irish mob and soon there were crime bosses from almost every nationality: Russian, Japanese, Chinese, Jamaican, Haitian, South African, Burmese, Cuban, Columbian and a lot of “Eastern European”.  The nationalities have cycled through film and TV over the years, with the crime boss du jour these days being from the Mexican Cartels. So many actors have played a crime lord over the years, we thought it would be fun to look at some of our favorites.

Mike G.

The crime boss is one of those characters that can be reduced to a pile of clichés in the hands of lazy writers/directors/actors. In reality, there are probably more “bad” mob boss roles on screen than good ones. Thus, I have a deep appreciation for those times when a unique spin is put on this classic role.  It wouldn’t be wrong to credit Martin Scorsese for perfecting this role, and its a good bet we’ll see another one in the upcoming The Irishman later this year. There are a ton of Italian/Mafia-type roles – some good, many not – but I ended up picking three less-traditional crime boss figures.

Bill “The Butcher” Cutting (Daniel Day-Lewis) in Gangs of New York

bill the butcher

This is probably not the crime boss people would think of for Scorsese films, but Daniel Day-Lewis created on of the most three-dimensional criminals in film history.  I actually think about this character frequently, in the midst of the anti-immigration rhetoric that is thrown around these days. The character was loosely based on William Poole – who was a “nativist” in the Five Points area of New York, and vehemently opposed to anyone not born in America. However, unlike the character in the film, Poole supposedly never engaged in acts of murder. Day-Lewis’ Butcher was undeniably brutal, but he was also articulate and strategic, not only with leading his gang in street fighting but in manipulating the politics of the neighborhood. Mob bosses seize and hold power by having people fear them, but Bill also got people to follow him via fear in a different way: he convinced them of an external threat and promised to help protect people from it. Remind you of anyone? Day-Lewis’ performance is just amazing – one of the best of his great career, although it was odd he was nominated for a “lead” actor Oscar and not supporting. This was probably due to the manipulations of now-disgraced producer Harvey Weinstein – kind of a real-life crime boss in his own right.

Signature Quote: “You know how I stayed alive this long? All these years? Fear. The spectacle of fearsome acts…That’s what preserves the order of things. Fear.”

DJ: I love everything Daniel Day-Lewis does, he is an amazing actor and like his other roles he brings Bill “The Butcher” to life. He is scary and intelligent and those are the worst villains.

Marcellus Wallace (Ving Rhames) in Pulp Fiction

marcellus wallace

Marcellus Wallace didn’t have a huge amount of screen time in director Quentin Tarantino’s 3-hour crime opus, but his character loomed large over the whole story. The two featured hit men in the story, Vincent (John Travolta) and Jules (Samuel Jackson) both work for Wallace and are the agents that spread fear in his name. Often, the mob boss’s hit man is a unique figure that defines the flavor of enforcement (often brutal) that the boss likes to dispense. Vincent and Jules are almost a comic odd-couple, with Jules favoring biblical quotes, but when it comes time to dole out death, they are proficient at their job. When we finally meet Wallace he ends up in a street chase with Butch (Bruce Willis), who owes Wallace for failing to take a dive in a boxing match. When both of them end up trapped in the basement dungeon of two redneck rapists (and “the gimp”), Wallace is disturbingly assaulted – becoming the only screen mob boss to ever be raped. After Butch rescues him, we know his revenge on the surviving rapist will be unthinkably brutal. He also shows, however, a certain “code” of street justice by allowing Butch to escape his debt, as long as he leaves town forever.

Signature Quote: “You hear me talkin’ hillbilly boy?! I ain’t done with you by a damn sight. I’ma get medieval on your ass”.

DJ: Not one of my favorite Tarantino films, but this film put Ving Rhames on the map. It’s an interesting pick and not one I would have even thought of but it’s a great performance and a very interesting character.

Al Swearengen (Ian McShane) in Deadwood

al swearengen

Speaking of cliched characters, the Western villain is another often-by-the-numbers role. He’s usually either a big landowner pushing the common folk around or a dastardly bandit with a quick draw. Swearengen is indeed a property owner and rules his criminal domain through fear and occasional brutality, but he’s mostly interested in serving up what the people want: namely drink, sex and gambling via his saloon/brothel The Gem. He doesn’t want to push the people out of town, he wants to bring them in. Most days he seems happy to oversee his semi-criminal enterprise from his quiet upstairs office. It’s only when his territory is threatened from outside forces that he turns violent. Although an outsized portion of his dialogue is profanity-laced, Swearengen is one of the best-written crime figures on television. Over time, we start to like his character, particularly in his relationship with adversary/reluctant partner Sherriff Bullock (played by Timothy Olyphant). It’s always said that the villain doesn’t think he’s a villain, and McShane does an amazing job of making what should be a despicable thug into a character you quietly root for. It’s not that Swearengen doesn’t know some of his actions are bad, but he has his own code that he lives by, and like many crime bosses, he takes pride in never breaking his word. I look forward to seeing his character back on screen for the Deadwood movie that just came out on HBO.

Signature quote: “Pain or damage don’t end the world. The world ends when you’re dead. Until then, you got more punishment in store. Stand it like a man – and give some back.”

DJ:  A series I have never seen but obviously has a huge following and is being talked about a lot. I have mad respect for McShane he is a great addition to any film or TV series. Maybe when I complete Bosch I will move to Deadwood.


I, of course, took a more traditional approach. There are so many to choose from films from the 30s and 40s have a ton. Leaving out Edward G. Robinson as Little Caesar, or films with Humphrey Bogart or Sydney Greenstreet should be a crime. I could pick three Al Pacino performances alone. I even thought of Vincent Donofrio as Wilson Fisk in Daredevil. But I can only choose three. I pick a very old one before getting more modern.

Cody Jarrett (James Cagney) in White Heat


I am going way back to the gangsters of the 20s and 30s. Cagney is best remembered for playing hoodlums and is probably best remembered for smashing the grapefruit into Mae Clarke’s face in The Public Enemy but that film is formulaic and Cagney plays a punk. When Cagney read the screenplay for White Heat he thought Cody Jarrett was run-of-the-mill, same as a lot of guys he had played, and he was tired of playing this role. The director Raoul Walsh decided to let Cagney have some leeway with the character and Cagney created Jarrett as a psychotic mama’s boy with migraine headaches. It may be one of the first complex bad guys on screen. Jarrett leads the surprisingly original named Jarrett Gang as they rob a train. He is married but the only person he really trusts is his Ma who helps him lead the gang, she is the only one to soothe his headaches. Jarrett lands in jail and an undercover agent ends up getting close to Jarrett like a surrogate mother. There is a great scene with the Telephone Game and a break out. Jarrett is ruthless and completely nuts willing to kill anyone. Cagney’s performance is legendary and does not glamorize the gangster of the 20s and 30s era like some other films did. The ending of the film a shootout at the top of a large gas storage tank is iconic.

Signature quote: “Made it, Ma! Top of the World!”

MG: No doubt a classic. I would agree that it set the stage for villains to have some complexity and not just 2-dimensional bad dudes. People still quote Cagney today, even if they have no idea what film the quotes are from.

Al Capone (Robert DeNiro) in The Untouchables


Al Capone could be the greatest real crime boss of all time. Nicknamed Scarface and responsible for the St. Valentine’s Day massacre Capone led the Chicago underworld and was finally brought down by unpaid taxes. Capone has been portrayed in TV and movies as long as both have existed but the most iconic performances and one of my favorites is Robert DeNiro in The Untouchables. Brian Depalma’s outstanding film is mostly about Kevin Costner’s Eliott Ness but DeNiro’s supporting role of Capone steals the show. As always DeNiro makes sure he looks the part. When Deniro played young Vito Corleone in The Godfather 2 he had an understated thoughtful performance but in The Untouchables he ratchets up the performance. It’s nice to see him calm and then to let loose. The scene when he talks about baseball and then proceeds to bash one of his henchmen’s head in is scary. Fear keeps the other underlings in line. The rivalry he and Ness have is riveting cinema and the two actors pull it off confidently. I also think with DeNiro’s other films his performance is often forgotten about or not mention amongst his best. Playing any run of the mill bad guy is easy but like Cagney above giving a nuanced performance and giving the villain a complex personality is not as easy.

Signature Quote: “I want him DEAD! I want his family DEAD! I want his house burned to the GROUND! I wanna go there in the middle of the night and I wanna PISS ON HIS ASHES!”

MG: This would have been my fourth one to write about – such a great film and powerful performance. The funny thing is, his screen time in this isn’t that much, but he makes such an impact with the time he has. I love the scene where he’s getting shaved by the barber and he gets nicked. The look he gives the barber is truly menacing. 

Tony Montana (Al Pacino) in Scarface


I can’t believe I picked two Brian DePalma roles, I am not even that big a fan of most of his films. For Al Pacino, I could have easily went for either of the two Godfather films (part 3 never existed), two of my favorite films of all time. His performances were out of this world and completely Oscar nomination worthy. But if we are talking about a crime boss I enjoy watching on film is there no other than Tony “Scarface” Montana. Pacino is completely over the top, sometimes hammy, no where close to his best performance but it’s so much fun. Seeing Montana as a young man leaving Cuba and working his way up the ranks of the Miami crime wave of the 80’s. He does what he has to do, he has ambition and balls finally taking his boss’s girl, business and his life. Ruling the cocaine empire of Miami Montana is ruthless and often careless. He builds an empire with paranoia and doesn’t even trust those close to him. Once at the top his cocaine addiction and paranoia get the best of him, losing all around him he is staked out at his mansion in a huge cocaine binge. He tries to fight off a Columbian cartel’s siege using gun after gun including a rocket launcher. The climax is thrilling and ludicrous in all the right ways. It’s a fun film to watch and a performance you won’t see in other Pacino roles. The film also doesn’t have a good guy, so it’s different than the other two I picked, this film is all about the “bad guy”.

Signature Quote: “Say hello to my little friend”.

MG: Interestingly, there haven’t been many films I can think of that have the crime boss as the main character. Tony Montana is one of those enduring bad guy characters that people love. It’s his shred of humanity that eventually does him in – when he won’t allow a car to get blown up that has kids in it. There are so many quotes from this film – “I always tell the truth, even when I lie.” and “All I have in this world is my balls and my word…and I don’t break them for no one.”