32. Road to Perdition (2002)

Director: Sam Mendes
Writers: Max Allan Collins, Richard Piers Rayner, David Self
Stars: Tom Hanks, Tyler Hoechlin, Paul Newman, Daniel Craig

This review is part of the feature:

The 33 Gangster Films You Can’t Refuse

In this adaptation from the beautiful graphic novel from Max Allan Collins (writing) and Richard Piers Rayner (art), Tom Hanks plays Michael Sullivan, an enforcer for Irish mob boss John Rooney (Paul Newman).

Rooney treats Michael like a son, but this dynamic is fractured by the reckless actions of Rooney’s actual son, Connor (Daniel Craig), whose betrayal leads to the brutal murder of Michael’s wife and youngest child. Gutted, Michael embarks on a chilling journey of vengeance across the snow-draped Midwest, with his surviving son, Michael Jr., by his side.

Director Sam Mendes brings together a stellar cast in this gripping, yet understated gangster epic. The performances are a masterclass in subtlety and intensity, with Hanks, Newman, and Craig delivering powerhouse portrayals that highlight the complex interplay of loyalty, betrayal, and familial bonds.

The cinematography by Conrad L. Hall is equally compelling, painting 1931 Chicago and the small-town landscapes of Illinois with a haunting, almost poetic beauty. Each shot is meticulously crafted, making the film as visually breathtaking as it is emotionally poignant.

The story is borrowed from the classic Japanese manga Lone Wolf and Cub, which is about an extremely skillful samurai who takes his son on a journey of revenge after being betrayed.

Thematically, Road to Perdition delves into the intricate relationships between fathers and sons, exploring how their love and loyalty can be both a source of strength and a cause of strife. The evolving dynamic between Michael and his son is moving, offering moments of connection and understanding amidst the violence and tragedy.

With its evocative storytelling, exceptional acting, and unforgettable imagery, Road to Perdition remains a standout in the gangster genre, as well as a deeply affecting meditation on family and redemption.

The 33 Gangster Films You Can’t Refuse


“It’s not just Italian American gangsters. It’s Cagney and Bogart movies, it’s Westerns. Americans seem to have some kind of fascination with outlaws in general. Maybe it’s because we were an outlaw nation to begin with. This nation was born of rebellion against authority, and in a weird way, that’s what these characters represent. That image is very attractive to Americans. It’s part of the national unconscious. It’s practically in our genetic code.”


― Steven Van Zandt in the article ‘A Harried Godfather struggles to balance his personal and professional lives’. By Matt Zoller Seitz in The Star-Ledger, 1-9-1999

Introduction

As far back as I can remember, I always loved gangster movies. Well, that’s not exactly true; I have always loved watching bad guys, so I definitely recognize myself in that Steven Van Zandt quote above – and I’m not even American. As a child, I loved cartoons and action films – like the James Bond movies – that featured inspiring villains.

Then, when I was 13, I saw GoodFellas for the first time. It immediately became my favorite film, my love for the gangster genre was awakened, and I have since watched countless gangster films. So now, more than 30 years later, I have decided to put together my personal ultimate ranking of gangster classics.

But what do I mean by ‘gangster film’? First, I had to get my criteria straight: gangsters must play a lead role in the movie. So is Heat a gangster movie? Definitely. Yes, fifty percent of the film is about the cops trying to catch the robbers, but those robbers play a huge role in the movie. In screen time alone, Neil McCauley’s gang can match most of the other gangsters on this list.

Of the final selection, I had the most doubts about The Untouchables and Lock, Stock and Two Smoking Barrels. The first is really about Elliot Ness and his special police force, but I still felt the gangsters play a very prominent part in the film. Robert De Niro’s Al Capone, in particular, is such a powerful gangster performance that the movie belongs on this list.

As for Lock, Stock: the main characters may not be arch criminals, but they are still up to their necks in crime. Besides, most of the other characters are legendary gangsters such as Hatchet Harry, Big Chris, and Barry the Baptist, so it’s pretty obvious it should be included.

One movie that didn’t make the cut is L.A. Confidential. A brilliant film, surely, but its ‘gangsters’ are mostly crooked cops, and therefore don’t count as gangster characters.

Great movies that almost made the cut: Scorsese’s Mean Streets, which I chose not to include because its characters are so low-level in the underworld and the film features few high-level mobsters.

The terrific A History of Violence, which is more an action thriller focused on the psychology of its characters rather than crime. And Bound, more an erotic thriller in which one main character (Joe Pantoliano’s Caesar) happens to be in the mob.

Movies that do live up to the criteria and almost made it, and therefore deserve an honorable mention: Gotti (the 1996 version), A Bronx Tale, The Roaring Twenties, Little Caesar, Scarface (1932), Eastern Promises, and The Public Enemy.

So now, without further ado, I present the 33 gangster films that define the genre for me… Just don’t go busting my balls about the selection, okay?

The 33 Gangster Films You Can’t Refuse

32. Road to Perdition

31. American Gangster

30. The Killing

29. King of New York

28. The Departed

27. In Bruges

26. Ghost Dog: The Way of the Samurai

25. Snatch

24. Get Carter

23. Point Blank

22. The Irishman

21. Bonnie and Clyde

20. Lock, Stock and Two Smoking Barrels

19. The Godfather: Part III

18. Donnie Brasco

17. The Long Good Friday

16. Menace II Society

15. State of Grace

14. Carlito’s Way

13. City of God

12. White Heat

11. Rififi

10. Once Upon a Time in America

09. The Untouchables

08. Reservoir Dogs

07. Heat

06. Miller’s Crossing

05. Casino

04. Scarface

In the month October 2026, a new gangster classic will be added to the list every day…

Stay tuned.

The Friends of Eddie Coyle (1973)


‘It’s a grubby, violent, dangerous world. But it’s the only world they know. And they’re the only friends Eddie has.’

Directed by:
Peter Yates

Written by:
George V. Higgins (novel), Paul Monash (screenplay)

Cast:
Robert Mitchum (Eddie Coyle), Peter Boyle (Dillon), Richard Jordan (Dave Foley), Steven Keats (Jackie Brown), Alex Rocco (Scalise), Joe Santos (Artie Van), Mitchell Ryan (Waters), Peter MacLean (Partridge, Manager of First Bank), Kevin O’Morrison (Manager, Second Bank), Marvin Lichterman (Vernon, Clerk, Second Bank)

In 1972, The Godfather was released – the most legendary gangster film of all time. A year later, director Peter Yates (Bullitt) delivered a different breed of crime film. While Don Corleone is a mob leader of almost insurmountable power and influence, the criminals in The Friends of Eddie Coyle barely qualify to cater Connie Corleone’s wedding.

The story revolves around small-time crooks in Boston’s underworld. These gangsters are based on the real Winter Hill Gang, later famously led by James ‘Whitey’ Bulger and later portrayed in films like Black Mass and The Departed.

Eddie Coyle (Robert Mitchum) supplies guns to a group of bank robbers connected to the Irish mob in Boston. He is also a stool pigeon for policeman Dave Foley (Richard Jordan). He thinks he’s friends with bar owner Dillon (Peter Boyle), who is also snitching to Foley without his knowledge. Dillon isn’t really his friend. Eddie has no friends: the title is ironic. Coyle gets tangled in a complex web of double-crosses and botched crimes, eventually becoming a target for the local mob boss.

The film’s strength lies in its authentic dialogue and characters. This is truly the bottom of the barrel in terms of criminal hierarchy. Eddie Coyle – perfectly portrayed by Robert Mitchum – is the ultimate low-life crook. It’s a bit of a slow burn, but the acting and writing are top-notch. And the ending must be the most unglamorous ending ever for a gangster film.

Rating:

Quote
FOLEY: “You remember Eddie Fingers? Eddie Coyle?” (“The bank robber, the one from Natick?”) “Nah, that’s his sidekick, Artie Van. Eddie doesn’t rob banks.”

Trivia
The film is based on the debut novel by George V. Higgins which is often praised for its authenticity. Legendary crime writer Elmore Leonard famously called it: “The best crime novel ever written.”

“Some people are better at being number twos”

In business, the entrepreneur or CEO at the top needs a unique set of skills to do their job perfectly. In my experience, what makes a leader great comes down to three things: having an inspiring vision for the future that others can relate to; knowing how to find the right people for the roles needed to achieve this vision and coaching them in that direction; and maintaining a relentless focus on what clients want and need, while executing the business to deliver it.

At Alex van Groningen, I learned from two very effective leaders – Alex and Melle – how this is done. During my own brief period as a manager, I discovered I’m a different type of leader. Not the centerpiece, but more of a behind-the-scenes guy: strategy, advice, and flawless execution of my own role.

In the leader’s seat, you must be very good at conflict resolution. I am not good at that. Silvio Dante, Tony Soprano’s number two (who spoke the quote above), noticed how difficult this is when he briefly took the top spot while Tony was incapacitated.

I can relate. I’m not good at dealing with unhappy people, nor does it energize me to constantly engage with others about their work and inspire them to do better. I much prefer to focus on my own job and deliver the best possible performance I can. In other words, I’m better at being number two. And I relate more to the consiglieri characters in movies.

Their bosses were often the big egos – think Michael Corleone, John Gotti, or Tony Soprano. They accomplished a lot, that’s for sure. But more than once, their number twos did things they couldn’t. A good number two understands the strategy like no other and often has an even better sense of the risks that might disrupt the strategic agenda. Like Tom Reagan in Miller’s Crossing realized that Leo shouldn’t protect Bernie Bernbaum because it would hurt their business.

Also, the consiglieri aren’t afraid to take decisive action when needed. Like when Silvio Dante whacked Burt Gervasi on his own initiative after discovering Burt was talking to their enemies in New York. In short, I relate more to number twos than to the boss in the top seat.

What about you – are you a top leader or more like a number two like me?

To give you a better sense of what makes a good second-in-command, here’s my Top 5 Consiglieri in Movies:

5. Genco Abbandando, The Godfather Part II

Genco Abbandando is a significant character in ‘The Godfather’ novel, though he hardly appears in the movies. In The Godfather Part II, he appears only in Vito’s 1920s flashback storyline, portrayed by Frank Sivero as a young man. Genco is shown as Vito’s childhood friend and ally in New York’s Little Italy, working at his father’s grocery store. Their early friendship is depicted, but he doesn’t actively advise Vito on-screen. Still, since he’s described as a legendary consigliere in the novel, I include him here.

4. Joe Armone, Gotti

In the movie Gotti, a realistic portrayal of John Gotti’s rise within the Gambino Family, Dominic Chianese (Uncle Junior in The Sopranos and Johnny Ola in The Godfather Part II) plays Joe Armone – consigliere first to Carlo Gambino and then to Paul Castellano, who was allowed to retire and start a coffee shop. There, he still gave advice free of charge. Gotti comes to see him, and Joe tells him the difficult truth: John broke the rules by whacking a boss without the commission’s approval. And now he’s breaking the oldest rule of Cosa Nostra: he’s appearing in the media. A mob boss doesn’t belong on the cover of Time Magazine, capeesh? But John Gotti, you know: you can’t tell him anything. He won’t listen to Joe’s sound advice and ends up in jail for life.

3. Tom Hagen, The Godfather

Tom Hagen served no fewer than three Corleones as consigliere: first Vito, then Sonny, and finally Michael. What makes him so effective is his supreme knowledge of law and business, which enables him to advise the Don on a wide range of affairs. The reason I rank him below numbers 1 and 2 is that Tom isn’t a very good wartime consigliere. He didn’t see through Barzini’s manipulations and the trap that eventually got Sonny killed. Still, he’s a very good guy to have in your corner.

2. Tom Reagan, Miller’s Crossing

While writing this blog, this is the first time I noticed his name rhymes with Tom Hagen. Funny, because Miller’s Crossing also starts with a Godfather-esque scene in the big boss’s office with his counselor Tom close behind him – very similar to the opening of the first Godfather film. So why is Tom Reagan a good consigliere despite acting against his boss’s will? Because of his wits, his sharp strategic mind, and his ability to see three steps ahead on the chessboard. It’s Tom who ultimately wins the gang war for his boss Leo. What more proof do you need of his skills?

1. Silvio Dante, The Sopranos

Yes, Silvio Dante is the ultimate consigliere. Extremely loyal and devoted to the Family. In The Sopranos, he constantly works on the guys, squashing dissent among the ranks and ensuring that Tony’s decisions are followed through to a T. He’s also not afraid to get his hands dirty when needed – like personally taking care of a number of rats for the crew (Jimmie Altieri and Adriana). In the final episode, when he’s in a coma, even the cold Tony seems to realize how good a friend and loyal associate Silvio has been.

READ ALSO: 10 Management Lessons From Highly Successful Gangsters