Small heist film Henry’s Crime, filmed at various Tarrytown locations in 2010 and reviewed here recently, has much in common with epic CIA drama The Good Shepherd.

In Henry’s Crime, Keanu Reeve’s character suffers from the sort of ennui of one whose life is just happening to him. Henry is not an active player in his own existence until he decides to rob a bank (not for the money, but for the life).

In The Good Shepherd, Matt Damon’s Edward Wilson is equally blah-humbuggy. He’s stiff and lifeless behind his thick 1950s glasses and starched shirts, as a CIA spy during the Cold War. Edward's marriage is also a Cold War, but it takes the whole movie for the wife to finally end it whereas Henry’s wife makes a fast run for it when he briefly goes to jail at the very beginning.

In Crime, Henry’ new romance thrives in the Music Hall, as he meets an actress in the lead role of the Cherry Orchard play under rehearsal. And here in Shepherd, the Cherry Orchard, fittingly Russian, is the drama again on stage at the Music Hall. Instead of Buffalo though, we are meant to be in Washington D.C.

Edward is watching the production with his Russian spy buddy (who complains it is funnier in Russian), when he sees his first (real) love across the audience. Laura is deaf and sweet, and despite his dumb luck in getting tricked into a fast shotgun marriage with the sexually aggressive Angelina Jolie, it seems Laura was meant to be “the one” had he chosen his own path.

The two starcrossed (doomed) lovers meet again after the play, years after Edward abandoned her on the beach in his college days at Yale, at the Set Back Inn (here, "Old Dominion Tavern"). This little scene, one of only minutes spent in our town in the duration of a lengthy two-hour-and-48-minute movie, is really its beating heart.

Choppy and incomprehensible at times, the film is constructed of layers of years, languages, plots, wars and espionage, which, you realize, is kind of the point. It’s meant to be as cryptic as the subject matter. Things are whispered that we aren’t meant to hear. 

But it’s the conversation spoken in the Set Back between our stiff "protagonist" and the deaf woman that rings clearest and truest of all. It provides a tragic glimpse of looking down the path of another life one could have taken, the better Plan B.

Laura asks if Edward has children. Yes, a boy, Edward, Jr. “Do you have anybody?” he asks. A cat, she says and the sadness is tangible. She says she often imagines a life with him, living in the small college town where he teaches poetry. She asks, “You once said to me you were afraid your life was already planned out for you. Are you doing what you want to do?” And he simply says, “Life has been full of surprises.”

Edward tries to send her off in a cab (Main Street is magically transformed with a whole set of beautiful vintage vehicles) but she gets out and they reunite physically in a hotel room. The only other moment shot in Tarrytown is when Laura awaits him again in front of the Music Hall and he insteads sends his right-hand man over to give her back the necklace he's had with him for years.

That’s the goodbye he gives her. And we know he will continue to choose a lesser, if bigger, life full of indecipherable and deadly secrets over the simple one full of love and truth he could have had.

Maybe Henry can help him.