100 Greatest Gangster Films: Road to Perdition, #25

Paul Newman and Tom Hanks in Road to Perdition (2002-R)
© DreamWorks

There was a story circulating in the New York underworld back in the 1980s about a meeting between Gambino crime family boss John Gotti and Vincent “the Chin” Gigante, the secretive, old-world style leader of the more powerful Genovese organization.

Gotti, according to reports that filtered back to law enforcement from mob informants, was boasting about how his son, John A. Gotti, had been formally initiated into the crime family. His son, Gotti said proudly, was now a made man, a “friend of ours” in the lexicon of the American Mafia.

Gigante was less than impressed.

“I’m sorry to hear that,” he said.

Fathers and sons and the mob. The smart ones don’t want the legacy to pass from one generation to the next.

Road to Perdition, a period piece about one branch of the Chicago crime family in the 1930s, is really a story about fathers and sons.

Paul Newman, in his last movie role, plays John Rooney, the patriarch of a mob family located just outside of Chicago. The organization is under the umbrella of Al Capone’s syndicate, but as is and was the case in Chicago, the mob—which is known as the Outfit—is more like a loose federation than a traditional Mafia family.

Rooney has a biological son named Connor (Daniel Craig) and a surrogate son named Michael Sullivan (Tom Hanks)—an orphan he raised. Sullivan is a hit man for the Rooney organization. Connor is a hothead who lacks his father’s intelligence and patience. His shortcomings prove deadly.

Told in flashback through the voice of Sullivan’s son Michael Jr. (Tyler Hoechlin), Road to Perdition examines the relationship between fathers and sons and the sense of honor, family and loyalty that both the traditional mob and blood relationships engender.

Can a gangster father keep his son from following in his footsteps?

And how far would he go to do so?

Those are the fundamental questions at the heart of this fascinating story. There’s plenty of violence and treachery, two staples of most classic gangster films. But there is another level to the narrative that makes Road to Perdition a different kind of mob movie.

Hanks is surprisingly good as the pragmatic and vengeful assassin who uses the skills developed in Rooney’s service to turn the aging mob boss’s world inside out. And Newman brings just the right blend of menace and cynicism to his character. Their scenes together are some of the best in the film.

Their verbal confrontation before Sullivan sets out on his one-man (plus a boy) crime spree defines the story.

“There are only murderers in this room, Michael, open your eyes,” Rooney says as he entreats his adopted son to reconsider his plan. “This is the life we choose, the life we lead. And there is only one guarantee: none of us will see heaven.”

“Michael could,” Sullivan says of his 12-year-old son.

“Then do everything that you can to see that that happens,” says a resigned and saddened Rooney.

What follows is not exactly what the aging mob boss had in mind.

Michael Sullivan, the hit man and orphan, chooses his family over the family, a decision that lends a level of nobility to what he sets out to do.

The plot is set in motion several scenes earlier as Michael accompanies Connor to a meeting with Finn McGovern (Ciaran Hinds), another mobster whose brother has been killed. The typical Irish wake for the dead gangster allows director Sam Mendes and writer David Self to set up the relationships and hint at the treacherous nature of the organization.

John Rooney toasts his dead associate with the hope that “he gets to heaven at least an hour before the devil finds out he’s dead.” Much drinking and dancing follow.

No one is quite sure why McGovern’s brother has been killed, but McGovern clearly holds Rooney responsible.

At a warehouse meeting the next night, Connor Rooney is supposed to iron out the problem with McGovern. Michael Sullivan is there to back him up. Unbeknownst to either, Michael Jr., in an attempt to learn what his dad does for a living, has slipped into his father’s car. He watches the meeting unfold by looking through a warehouse window.

What he sees is the short-tempered Connor fly off the handle and gun down McGovern. Michael Sullivan Sr. then kills two of McGovern’s associates to protect Connor Rooney.

It’s what he does.

As they leave, they discover young Michael. In one of several rain-soaked scenes that add to the film’s gloomy atmosphere, Michael Sr. tells his son, “You are not to speak of this to anyone.”

Connor is not comfortable with that arrangement, however, and a short time later goes to Sullivan’s home. He mistakenly kills Sullivan’s younger son Peter (Liam Aiken) and then guns down Sullivan’s wife Annie (Jennifer Jason Leigh).

This sets up the father-son dynamic that defines the rest of the movie.

Michael Sullivan first goes to John Rooney for justice, but is told instead that they are all murderers and to let it go. In fact, Rooney has chosen his own blood, Connor, over the son he loves better, Sullivan.

Michael Sullivan then travels to Chicago with his one surviving son and namesake to meet with Frank Nitti (Stanley Tucci) and ask for permission to do what he has to do—kill Connor Rooney. Tucci, in a well-acted supporting role, tells him that while the organization is sorry for what happened, Connor Rooney is being protected.

It’s business, he says.

With that, Michael launches his father-son crime spree, setting out to rob banks where the mob has stashed its money. This, he reasons, will force Capone to grant him his wish.

Along the way, young Michael learns how to drive a car so that he can handle the getaways and father and son, who have never spoken that much, learn about one another.

Feeling guilty and responsible for what has happened, Michael Jr. asks his father if he loved his brother Peter more than him, pointing out that he always treated Peter differently.

“Well, I suppose it was because Peter was just . . . such a sweet boy,” Michael Sr. says. “And you, you were more like me. And I . . . didn’t want you to be.”

In another conversation that underscores how their relationship is developing, the younger Michael, after a bank robbery, asks what his take will be. His father asks how much he wants.

“Two hundred dollars,” the boy says.

“Okay, deal,” says his father.

Michael Jr., who is eating at a diner at the time, stops to consider, then asks, “Could I have had more?”

“You’ll never know,” says his father.

The Sullivans rob several banks while staying one step ahead of a psychotic hit man, Harlen Maguire (Jude Law), sent by the Capone organization.

In addition to avenging the murders of his wife and youngest son, Michael Sullivan’s goal is to get to Perdition, a lakeshore town where his wife’s relatives live and where he hopes to find safety for his surviving son. This allows for the less than subtle double-entendre that is the movie’s title.

Michael Sr., the Rooneys, Nitti, an unseen Al Capone and all the other gangsters have clearly chosen a life that drives them down the road to hell.

Michael Jr. has a chance to go in a different direction. And his father will do everything in his power to help make that happen.

HIT: The movie captures the bleak, film noir feel of the 1930s gangster genre. This is due in large part to cinematographer Conrad L. Hall, whose work was recognized with an Academy Award.

MISS: The premise of robbing banks and only taking the mob’s money is a bit of a stretch. It’s hard to imagine gangsters like Capone letting a banker off the hook after he explains that we’ve been robbed of your money, but no one else’s. Those guys don’t need the Feds to insure their deposits.

REALITY CHECK: Newman wanted his John Rooney character to speak with the hint of an Irish accent. So he got a tape made by Irish-born author Frank McCourt (Angela’s Ashes) and studied his voice inflections and speech patterns.

BEST LINE: “Natural law: sons are put on this earth to trouble their fathers,” says Rooney as he complains about his hotheaded son Connor to Michael Sullivan, the orphan he has raised as a son and who is, in many ways, closer to him than his own blood.

WHAT THEY WROTE AT THE TIME: “Road to Perdition ponders some of the same questions as The Sopranos, a comparably great work of popular art, whose protagonist is also a gangster and a devoted family man. But far from a self-pitying boor lumbering around a suburban basement in his undershirt, Mr. Hanks’ antihero is a stern, taciturn killer who projects a tortured nobility. Acutely aware of his sins, Sullivan is determined that his son, who takes after him temperamentally, not follow in his murderous footsteps.”—Stephen Holden, New York Times

CASTING CALL: Anthony LaPaglia was cast as Al Capone and was in one scene, but the scene was cut after Mendes decided that Capone was a more ominous presence unseen.

DON’T FAIL TO NOTICE: Jude Law had a make-under before he appeared as the psychotic photographer/hit man Harlen Maguire. He was given a sallow, almost yellow skin tone, his gum line was lowered and his teeth were made to look rotten.

PIVOTAL SCENE: When the Sullivans avoid Maguire, the hit man sent to kill Michael Sr. at the diner, they realize that the mob has not only refused Michael’s request, but has now decided to eliminate him. At that point, Michael has two choices, flee or fight back. He decides to fight back and launches the crime spree—bank robberies and shootings—that dominates the second half of the movie.

BET YOU DIDN’T KNOW: In the novel on which the movie is based, Michael Sullivan’s character is so violent he is known as the “Angel of Death.” The movie script softened the character, partly at Hanks’ request. And the hit man character played by Law was created for the movie.

BODY COUNT: Twenty-one.

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[Reprinted from The Ultimate Book of Gangster Movies by George Anastasia and Glen Macnow. Available from Running Press, a member of The Perseus Books Group. Copyright © 2011.]

George Anastasia, Glen Macnow

George Anastasia is a crime reporter for the “Philadelphia Inquirer” and author of several books, including “Blood and Honor” which Jimmy Breslin called “the best gangster book ever written.”

Glen Macnow was a writer for the “Philadelphia Inquirer” and “Detroit Free Press.” He is currently a talk-radio host on 610-WIP in Philadelphia.

George and Glen have co-authored “The Ultimate Book of Gangster Movies.”