
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.


















