Vito Corleone, a name every movie fan knows. It’s also a name that would obviously top a list of great movie mob bosses. For that reason you won’t find him here. Still it was pretty easy finding other mob bosses that deserve a tip of the hat. That is what we are looking at in today’s Phenomenal 5. The movies have been fascinated with mobsters for decades which means I had a ton of bosses to choose from. With that in mind I wouldn’t call this the definitive list. But there is no denying that these five movie mob bosses are nothing short of phenomenal.
#5 – Frank Costello (“The Departed”)
In Martin Scorsese’s “The Departed” Jack Nicholson plays Frank Costello. No, not the real-life Italian mob boss who once ran the Luciano crime family. A fictional Irish mob boss based on “Whitey” Bulger. As you would expect, Nicholson is calm, cool, and charismatic. He gives us a streetwise Boston mob boss who is trusted by his men but who also holds a pretty big and significant secret. It should be no surprise that Scorsese knows how to portray a mob boss or that Nicholson can deliver that vision in spades.
#4 – Al Capone (“The Untouchables”)
Robert De Niro as a mob boss. Talk about a formula ripe with potential. Brian De Palma gives it to us in his 1987 Chicago gangster picture “The Untouchables”. This is a very different mob boss depiction from any others on this list. In many ways it is a stylized portrayal. De Niro is asked to go big and he REALLY goes big. But that is one reason his Al Capone is so much fun. “The Untouchables” is a great movie and Eliot Ness is its focus. But De Niro nails every scene he has and he always leaves you anxious for him to show up again.
#3 – Leo O’Bannon (“Miller’s Crossing”)
Most fans of the Coen brothers hold “Miller’s Crossing” in pretty high regard. This neo-noir gangster movie from 1990 takes its inspiration from a number of sources, but ultimately it is a Coen brothers movie through and through. In the film we are introduced to Irish mob boss Leo O’Bannon (played with such controlled energy by Albert Finney). Leo knows how things work in the Prohibition era and he’ll push his weight around whether it’s with bullets, brawn, or his brain. Finney is superb and the Coens give him so many great scenes to define his character.
#2 – Bill the Butcher (“Gangs of New York”)
It’s Martin Scorsese again. Instead of Boston this time he is in Lower Manhattan’s Five Points. It’s 1846 and the territory is ran by William “Bill the Butcher” Cutting. His influence and power reaches all through Five Points and beyond and he’s not afraid to flex his muscle sometimes in incredibly violent fashion. Bill the Butcher is such an intriguing character but what makes him shine is the performance by Daniel Day-Lewis. He wears the bizarre suits, top hats, and the curly mustache with gusto. But while he sometimes seems otherworldly, he slams us back to reality with his bonafide mean side. A great character.
#1 – Caesar “Rico” Bandello (“Little Caesar”)
He simply had to be at the top of the list. “Little Caesar” was Edward G. Robinson’s star making role. It granted him instant fame and started what would be a long line of gangster pictures for an actor with one of cinema’s most recognizable mugs. “Little Caesar” is also important because it is widely considered to be one of the first straight up gangster movies. Robinson is so perfect as Rico, a small-time hood who joins a gang and rises through the ranks by any means necessary. That sometimes means stealing and sometimes killing. His time at the top isn’t without conflict both externally and internally. It all leads to one fantastic finish. Little Caesar himself was an easy choice for #1.
So what do you think? Agree or disagree with my picks? I would love to hear why. Also be sure to share some of your favorite choices of movie mob bosses. Head down the comments section below and sound off.
Keith & the Movies 
With the exception of Little Caesar (which I haven’t seen), I’m on board with all of these choices. Especially Leo O’Bannon as the Danny Boy scene is a masterpiece.
O’Bannon is so good, right? So many great scenes none better than the Danny Boy scene. Man I love it.
Keith, nice call with Little Caesar. I’d add Paul Newman for Road to Perdition. Which then makes me think of (I don’t know why) On the Waterfront with mob boss Johnny Friendly played by Lee J. Cobb.
Cobb is a great mention Cindy. Didn’t even think about him. Newman was also really good in RtP. I love that movie!
The score pulls on my heartstrings.
Yes. So strongly. Everything works in that film.
BTW, hope you’re doing well. Hope you are are getting some things done in your time away.
Keith, good call not listing Vito. I really thought, “yep, Vito will be number one” hehe
Automatically, right? I figured everyone would instantly move to him. Such an iconic performance.
Oh man, I LOVE mob movies, so I naturally love this list, and can totally understand why you don’t have Vito on here – he is legendary for a reason. Great picks Keith!
Thanks Zoe. I kinda love them too. And how could I not have put Vito first. Setting him aside is the only fair choice. Have you seen most of these?
Yep yep – will have to catch Little Caesar though, but I am sure to keep my eyes peeled for it!
Definitely look out for it! It is a mob movie lovers classic!
This was a great list. Defied my expectations of who I thought would be on it. Only thing I would change is Bill the Butcher would be in first place. Day-Lewis should have 4 Oscars cause he should have won for this. So damn charismatic.
No arguments with DDL in first. I love that performance SO much. I think Robinson’s work is just so good. In many ways it set the standard for an whole decade of gangster flicks.
Vito Corleone has to be mine, he’s the best.
Yep. But as I wrote, I had to leave him out. He would instantly be everyone’s #1
That is very true Keith. He is the ultimate mob boss.
Tops. Brando gives us such an iconic movie character. He is one of those guys who everyone knows. Even if you haven’t seen the movie you have heard his name.
Iconic is exactly what he is, I even have a Vito Corleone T-shirt.
Nice!
It’s great to see Leo O’Bannon on here; I love Miller’s Crossing and think not enough people have seen it. Truthfully, I found Gangs of New York to be one of Scorsese’s more middling efforts but Daniel Day-Lewis’ performance is incredible for sure. Nice list Keith.
O’Bannon is great and I 100% agree with you. You just don’t hear people talking about Miller’s Crossing. Great film.
I get what you’re saying about Gangs. I think it’s a bit too long and draggy in places. But I can’t tell you how mesmerized I was by DDL’s Bill the Butcher.
Great shouts. Would only add the On the waterfront guy which someone had already mentioned.
I agree. Can’t believe I forgot about him. That Lee Cobb performance is so incredibly good.
You can’t include them all!
I love each of these guys. Not a bad pick among them. The only person I am disappointed not to see here is Uncle Paulie from GoodFellas. Well, Michael Corleone, too, but I’m guessing you put him in the Vito category.
Others I like…if they all count…
Tony Montana – Scarface
Frank White – King of New York
Nino Brown – New Jack City
Lucky Luciano – Hoodlum
Carmine Falcone – Batman Begins
Frank Lucas – American Gangster
Li’l Ze – City of God
Sooo many to chose from, right? Frank Lucas was so close. Loved that character and performance. Glad someone else mentioned him.
I’m embarassed to admit that I’ve only seen Jack Nicholson as Frank Costello and none of the rest. But I can say that Nicholson gave a spectacular and eerie performance! That movie in general is amazing.
Oooooh you have some new movies to see. Definitely look these others up. They’re all uniquely different so I think you’ll find something to enjoy there.
Great choices. Also Paul Cicero from Goodfellas.
Nice one. Loooong consideration of him. Such a great choice.
Little Ceasar! Inspired choice, Keith. Glad you left Don Vito off (But he would have been my default too, lol, and Michael wasn’t too shabby either). Great list, man!
Thanks Vic. Little Ceasar kinda set the standard in his day, didn’t he? Just impossible not to include him. Heck, much of Robinson’s career sprung from his incredible work in this film.
Great call on Bill the Butcher. Daniel Day Lewis is so good in the role. I’m not sure who else I’d have considered outside The Godfather “bosses” – perhaps Pacino in Scarface or a left field choice: Sly Stallone in John Landis’ Oscar!
I intentionally stayed away from the Godfather. I think we all gravitate towards them automatically. I love the Oscar pick! Definitely outside of the box.