Whatta you lookin' at? Welcome to WatchMojo, and today we’re counting down our picks for the most ruthless gangsters featured in movies. Beware of spoilers!
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00:00 "Talk about vengeance. Is vengeance gonna bring your son back to you?"
00:04 Welcome to WatchMojo, and today we're counting down our picks for the most ruthless gangsters
00:11 featured in movies. Just so we're clear, they have to be fictional, so don't go looking for
00:16 Henry Hill from Goodfellas or any of his fellow real-life wiseguys. Also, beware of spoilers.
00:22 "Say hello to my little friend!" "Okay, you wanna play rough? Okay."
00:30 Number 10. Don Logan, Sexy Beast. "Are you gonna do the job?
00:36 It's not a difficult question. Yes or no?" "Don." "Say it." "No." "Yes."
00:47 Sir Ben Kingsley is probably not the first actor one might think of as a gangster. But as Don Logan,
00:54 he's unforgettable. Don approaches his old friend Gal, who's retired in Spain for one last job.
01:00 However, even though Gal desires to enjoy his retirement, Don insists. Profane and completely
01:07 self-absorbed, Don Logan is one of the most overbearing movie characters in cinema.
01:12 "Am I happy here? I won't let you be happy, what should I?"
01:17 His inability to let go of what he wants is profoundly childish. Yet his intense,
01:22 menacing pursuit of his goals is also terrifying. Bottom line,
01:27 Don is the embodiment of the phrase, "With friends like these, who needs enemies?"
01:31 "No, Don." "Friday!" "I won't be there." "You will?" "No, Don." "Yes, yes, yes, yes, yes!"
01:37 Number 9. Michael Sullivan - Road to Perdition "You saw everything?"
01:41 "Jesus, you are not to speak of this to anyone."
01:51 Tom Hanks makes for another unlikely gangster, but he hits this role out of the park, just like his
01:58 other performances. Playing Michael Sullivan Sr., a mob enforcer for a Chicago gang, Hanks' character
02:05 is raised like a son by the gang's leader, John Rooney. However, things turn sour when Rooney's
02:10 biological son, Connor, orchestrates the murder of nearly all of Sullivan's family. Forced to go on
02:17 the run with his own son, Michael Sullivan Jr., the protagonist seeks revenge for his family's
02:22 deaths, while also struggling to secure a better life for his son. "Tomorrow when they find out
02:27 we're gone, they're gonna come after us. I have to protect you now." "Please, Paul."
02:34 Hanks delivers a fantastic portrayal of Sullivan, one of brutal violence mixed with fatherly
02:39 instinct. Good or bad, he's still a dad. "You never wanted me along anyway. You think it's
02:45 my fault this happened." "Stop it, Michael. It was not your fault." Number 8. Vic Vega aka Mr. Blonde
02:53 - Reservoir Dogs "Are you gonna bark all day, little doggie? Or are you gonna bite?" Each member of the
03:01 gang this film focuses on is memorable in their own ways, but some personalities are bigger than
03:06 others. In every crew, there is a loose cannon, and in this one, it's Mr. Blonde, real name Vic Vega,
03:14 or Toothpick Vic. Mr. Blonde is the man responsible for his gang's diamond heist turning into a blood
03:20 bath. "That's your excuse for going on a killed crazy rampage?" "I don't like alarms, Mr. White."
03:25 A smooth-talking psychopath, Mr. Blonde can be charming with his dry humor and amusing turns of
03:31 phrase. However, his infamous torture of a cop the crew has captured, while dancing to Stuck in the
03:37 Middle with You, illustrates that beneath the exterior lies a profoundly disturbed individual.
03:43 "I got something I think you might want to see, though." "What?" "Surprise. I'm sure you'll like it.
03:48 Come on." Number 7. Lil Zay, aka Lil Dice, City of God.
03:54 Easily the youngest entry on our list, Lil Zay is the young kingpin of the City of God,
04:04 a neighborhood of Rio de Janeiro. A violent sociopath, Lil Zay, known as Lil Dice as a child,
04:11 has risen to the top of his local underworld by being willing and eager to kill. His glee for
04:16 murder makes nearly every scene he is in full of tension, since anyone could die if he decides to
04:22 indulge in his favorite pastime. The loss of his best friend Benny removes what little restraint
04:35 Zay previously had, prompting him to engage in a lengthy gang war. Ultimately, as is the case
04:41 with many gangsters, the many enemies Zay makes eventually catch up with him.
04:48 Number 6. Kaiser Soze, The Usual Suspects. "Who is Kaiser Soze?"
04:57 "He's supposed to be Turkish. Some say his father was German. Nobody ever believed he was real.
05:04 Nobody ever knew him or saw anybody that ever worked directly for him."
05:08 Some serious spoilers ahead on this one. Even criminals have a boogeyman. Before John Wick,
05:14 the name that made them reconsider their life choices was Kaiser Soze. After the criminal
05:19 with disability named Verbal Kint is caught, he recounts how he and several of his fellow
05:24 gangsters were enlisted by the shadowy crime boss Kaiser Soze for a job gone awry. Soze never shows
05:31 his face, and few who work for him even know it's him they're working for. "He becomes a myth,
05:37 a spook story that criminals tell their kids at night. Rat on your pop and Kaiser Soze will get
05:43 you." By the film's end, it's clear that Kint's story is partially fabricated, with details drawn
05:48 from his surroundings. Not only that, Kint is Kaiser Soze. Machiavellian and half-myth,
05:55 Kaiser Soze is a master criminal and a legendary gangster. And like that…
06:00 "Greatest trick the devil ever pulled was convincing the world he didn't exist.
06:04 And like that, he's gone."
06:11 Number 5. Frank Costello, The Departed. "When I was your age, they would say we could become
06:17 cops or criminals. Today, what I'm saying is this. When you're facing a loaded gun,
06:28 what's the difference?" A Boston mob boss of Irish descent,
06:32 Frank Costello rules his city's criminal underworld with brutality and brains. He has informants
06:38 within the police force and personally tips off the FBI about his rivals, allowing him to remain
06:43 one step ahead of both his competition and the cops. When Billy Costigan joins his organization,
06:49 Frank suspects him of being a rat, but also comes to see himself in the young man. Throughout the
06:54 film, Frank's demeanor veers from being violent one minute to laugh-out-loud hilarious the next.
06:59 And given that it's Jack Nicholson playing him, he just oozes charisma every time he's on screen.
07:13 He may appear careless, but this is one meticulous and crafty gangster.
07:18 "The only one who can do what I do is me. A lot of people had to die for me to be me."
07:25 Number 4. Jules Winfield, Pulp Fiction. "What does Marcellus Wallace look like?"
07:32 "What? What country are you from?" "What? What?" "What ain't no country I ever heard of!"
07:39 Quentin Tarantino movies are loaded with colorful criminals and ne'er-do-wells.
07:44 While big boss Marcellus Wallace is more of a mobster archetype, his enforcer/hitman Jules
07:50 Winfield is one bad mother. Effortlessly cool in basically everything he does, Jules is among
07:57 the most quotable gangsters out there. The apartment scene alone is downright legendary.
08:02 "And I will strike down upon thee with great vengeance and furious anger those who attempt
08:10 to poison and destroy my brothers." Many of his expressions and jokes have become the sources for
08:16 countless memes. However, a near-death experience causes Jules to re-examine his line of work.
08:21 He may quote the Bible often, but it's only after witnessing this miraculous event that Jules is
08:26 inspired to be the shepherd rather than the tyranny of evil men. We'd be down to watch him
08:32 walk the earth forever. "And you will know my name is the Lord when I lay my vengeance upon thee."
08:41 Number 3. Michael Corleone – The Godfather Franchise
08:45 "Don't tell me you're innocent because it insults my intelligence. It makes me very angry."
08:53 A quintessential embodiment of the rise and fall of a gangster, Michael Corleone is someone you
08:59 don't want to mess with. Initially, Michael wants nothing to do with the family business of organized
09:05 crime. However, the murder of his first wife and the needs of the family force him to step up and
09:10 take charge, becoming the new Godfather. "There are things being negotiated now that are going
09:15 to solve all your problems and answer all your questions. That's all I can tell you now."
09:20 However, as he navigates the leadership of his crime syndicate, he gradually loses his way,
09:26 alienating or executing members of his real family. Michael Corleone could easily take the
09:31 top spot. He's one of the most iconic gangster characters ever, and Al Pacino's performance
09:37 is unforgettable. Even so, there are some fictional gangsters who are equally, or even more,
09:43 legendary. "If anything in this life is certain,
09:45 if history has taught us anything, it says you can kill anyone."
09:52 Number 2. Tony Montana - Scarface "You calling me a liar?
09:56 Now what you calling me?" Al Pacino has played a lot of great gangster characters. Among them
10:04 is Carlito Brigante from Carlito's Way, which was even made by the same director as Scarface.
10:11 Yet, few of Pacino's roles, or indeed, few other gangsters in any medium, are as electrifying as
10:17 Tony Montana. A Cuban immigrant, Tony works his way up through the criminal underworld,
10:22 from its lowest gunman to become a drug kingpin of Miami. "Do you know what a husser is, Frank?
10:27 That's a pig. That don't fly straight. Neither do you, Frank." Pacino's captivating, unhinged
10:36 performance is endlessly watchable. He brings to life a character whose journey is a twisted tale
10:41 of the American dream, a rags to riches story of blood and drugs. If there's a poster child for the
10:47 excess and danger of the gangster life, it's Tony. "Brother, do you want to go to war? Come on,
10:52 do you want to go to war? We'll take you to war, okay?" Before we unveil our top pick,
10:56 here are a few honourable mentions. Tom Regan - Miller's Crossing
11:00 He's a smooth customer who always looks out for himself. "Giving up Bernie was the only way I
11:06 could see to straighten things out for Leo. I thought you said you didn't care about Leo.
11:12 I said we were through, it's not the same thing." Nino Brown - New Jack City
11:17 A cash money gangster who knows how to make change. "If I was what? Say it again, what'd you say?
11:23 Nothing. That's what I thought you said, because that's what I got right now, nothing."
11:30 Vincenzo Caccotti - True Romance A one scene wonder, but oh so memorable.
11:36 "Who are you?" "I'm the Antichrist. You got me in a
11:40 vendetta kind of mood. You tell the angels in heaven you've never seen evil so singularly
11:45 personified as you did in the face of the man who killed you."
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12:02 Number 1. Vito Corleone - The Godfather Franchise
12:08 "Now you come to me and say, 'I'm Corleone and give me justice.'
12:12 You don't ask for respect. You don't offer friendship."
12:19 The face of mobsters everywhere, Vito Corleone is the original Godfather. Vito comes to America
12:25 after fleeing Italy following the death of his parents at the hands of a local gangster. In the
12:30 States, he works his way up to become a respected figure in New York, eventually assuming the role
12:35 of the Godfather. His old-school gangster ways prioritize the welfare of his neighborhood and
12:40 friends rather than violence meant for profit. Whether he's played by Marlon Brando or Robert
12:56 De Niro, Don Vito is the OG to end all original gangsters. And for anyone who thinks otherwise,
13:03 well, Don Vito has a proposal. Is there a movie gangster you're whacking your
13:17 foreheads that we forgot? Bark all day at us in the comments, little doggies. Just don't bite.
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13:34 [Music]