What ‘Road to Perdition’ Taught Me About Leaving Legacies For Our Kids

It had probably been close to a decade since I’d watched Road to Perdition, a movie that I first saw during its theatrical run in 2002. This crime flick contains three elements that, on their own, drastically improve the odds of earning my cinematic affection: it takes place in the Prohibition era, it was partially filmed in the Chicago area, and it stars Tom Hanks.

With the wheels for a favorable review already greased, Road to Perdition more than earned a place on my list of all-time favorite movies, with sensational acting by Hanks and pretty much everyone who appears on screen (Paul Newman! Jude Law! Stanley Tucci!), Academy Award-winning cinematography, and a beautifully heartbreaking score by Thomas Newman.

Not only that, the film’s story serves as a poignant meditation on fatherhood. Rewatching the movie last weekend, and now a father myself (expecting a son, no less), the film’s exploration of the father-son dynamic struck me much more deeply.

A brief plot refresher (Spoilers aplenty): Michael Sullivan (Tom Hanks) is a mob enforcer for his adoptive father, John Rooney (Paul Newman). Cold-blooded murder and fierce intimidation are how Sullivan earns his daily bread to support his wife and two young sons. When Sullivan’s oldest son, Michael, gets curious about his physically and emotionally distant father’s line of work, he inadvertently witnesses his dad’s involvement in a mob confrontation gone wrong. Sullivan’s wife and younger son are then brutally murdered by Connor  –  Newman’s biological son and the trigger-happy source of the misguided mob hit –  who thinks he is murdering the child witness and solving his problem.

Sullivan and Michael are forced to go on the run, offering heretofore unknown father-son bonding opportunities in six weeks on the road between Rock Island, Illinois, and Chicago.

His dying act is one of simultaneous violence and love. He sacrifices his soul so that Michael can keep his unblemished.

As the plot unfolds, the body count continues to rise as Sullivan ironically uses violence to attempt to provide a clean slate for his son  –  robbing banks with Michael’s assistance and ultimately killing both Connor and his father. The life of crime seems to be behind them when they retreat to a relative’s off-the-grid home to start a new chapter. Unfortunately, the hitman who was sent after them earlier in the film meets them there, and the movie ends with a dramatic confrontation in which young Michael tries to muster the courage to shoot the hitman, while his father lies wounded and dying. The elder Sullivan ends up reaching for a gun and pulling the trigger to kill the hitman, saving his son’s life  –  and soul  –  by sparing Michael the trauma of having to take someone’s life and continuing the cycle of violence in the Sullivan family.

At the end of the film, all of the loose ends are tied up so that Michael can seek an honest life with a farmer couple that they previously met on their road trip. Through all these twists and turns, the film deftly plays with so many issues associated with fatherhood  –  love, duty, honor, guilt, shame, regret, and sacrifice.

After my most recent viewing, I kept dissecting Hanks’ character and his complex rationales and ethical code. He engaged in a life of violence and crime out of devoted duty to his adoptive father. That same father expresses regret at having led his two sons down this path, and urges Sullivan to do whatever he can to make sure Michael doesn’t enter the family business. While Sullivan knows that his criminal acts are wrong and feels tremendous guilt for how it has destroyed his immediate and extended family, he’s also compelled to engage in even more bloodshed to right the wrong , and rationalizes that he must kill his adoptive father and brother in order to take the old man’s advice and save his son.

In the end, all the violence catches up to Sullivan ,  and also inexplicably turns out to be the only way for him to ensure Michael’s purity. His dying act is one of simultaneous violence and love. He sacrifices his soul so that Michael can keep his unblemished. While most of Sullivan’s violence in the film comes out of self-preservation or professional duty, this final act is one of bravery and devotion to his son. Sullivan is redeemed for all time in Michael’s eyes.

Parents are often in the remarkable position of instantly earning their children’s admiration simply through the circumstance of being their parents.

There’s a lot to unpack in Hanks’ desolately haunting performance as Sullivan and Tyler Hoechlin’s impressive turn as Michael. There is intentionally very little dialogue in the film, so the acting does much of the heavy lifting of setting up character dynamics. Early in the film, we hear the deafening silence when Sullivan is at the dinner table with his family or riding in the car with Michael. We see how much Michael simultaneously adores and fears his father , covering for his dad’s secretive (and as-yet-unknown-to-Michael) occupation by creating an elaborate story about his “missions for the president” when his younger brother asks some probing questions about why their father is always working at night. When he witnesses his father killing gangsters with a machine gun, the agony of his grief and disbelief is heartbreaking. So too is Sullivan’s shame and regret.

Parents are often in the remarkable position of instantly earning their children’s admiration simply through the circumstance of being their parents.

While this admiration ebbs and flows with age, it’s also incumbent on the parents to ensure that the admiration is eventually earned and that the qualities they are exhibiting are worthy of such admiration.

While I am fortunately not a mob enforcer, the movie did get me thinking quite a bit about what legacies get passed down through the generations in a family. What are the things ,  positive or negative , that my grandfather passed on to my father and that my father has passed down to me? And it’s not just fathers doing the passing. These legacies are not necessarily as obvious ,  like a life of crime , as they are in the film. I’m talking more about intangible but essential qualities  –  insecurities, fears, tendencies, and worldviews.

Your parents’ experiences as children undeniably shaped the way they parented you. As we move down the family tree, the way your grandparents parented your parents and the way your parents parented you has a natural effect on the way you parent your children. How deep does this go?

One thing is certain: taking an honest look at your upbringing reminds you anew of the blessing of your own parents and everyone else who devotes themselves to the mission of raising children.

The passing down of these legacies can be good or bad. Your parents could correct something negative that their parents did. They could over-correct or under-correct. They could also do the exact same good or bad thing that their parents did ,  even if they promised themselves that they would be different. And you could do all those things, too.

As we have embarked on our own parenting journey, my wife and I have forced ourselves to begin taking stock of the legacies that each of us brings from our families ,  and now that it’s our turn , deciding how we want to shape the next generation.

Much like Sullivan, sometimes you can’t even recognize the legacy until someone you love sees you holding the smoking gun.

It’s incredibly difficult but also imperative that there be no golden calves in this process. One thing is certain: taking an honest look at your upbringing reminds you anew of the blessing of your own parents and everyone else who devotes themselves to the mission of raising children. It’s probably the most difficult and frequently thankless vocation on the planet , but it’s also the most important.

Road to Perdition serves as a cautionary tale by coming at this truth from the angle of regret. Both Sullivan and Rooney wish they had been better fathers, but only one of them realizes it while there is still some time left to recorrect and connect with his son.

When Sullivan dies, he equips Michael with an opportunity to take a noble path . And that’s exactly what a father should do for his son.

This story was republished from Dad Has a Blog. Read Matt Paolelli’s original post here.