Jack Goes Boating (2010)

Gone too soon

In light of Phillip Seymour Hoffman’s recent death, I went back and watched his directorial debut Jack Goes Boating. I’m glad I did. It’s fairly straightforward yet insightful, touching, honest movie, about the difficulties in finding and maintaining romantic relationships. I liked it very much, though it left me saddened. I wish he were still around.

I’d never seen Jack before, but have vague memories of NPR talking about it when it was released. I wasn’t quite sure what to expect, but figured if nothing else I’d enjoy Hoffman’s dynamic performance. He’s one of my favorite actors. His roles in Magnolia, Capote, Synecdoche, Scent of a Woman, Doubt and the Master are diverse, nuanced, affecting and always interesting. What I found in Jack was a calm (almost quiet) film about a frumpy, awkward guy, struggling to find emotional connection.

The movie’s based on a play by the same name, written by Robert Glaudini. Hoffman plays Jack, a limo driver. He wears ill-fitting clothes, a winter hat year round, and listens to reggae music because of its “positive vibe.” Most of the time he looks disheveled, but cleans up OK for work. Fellow driver Clyde (John Ortiz; Silver Linings Playbook, Public Enemies) is his buddy. He likes Jack, maybe more than Jack likes himself.

Clyde and his wife Lucy (Daphne Rubin-Vega) invite Jack over to dinner. It’s a blind-date set-up with her equally shy co-worker Connie (the Wire’s terrific Amy Ryan; Win Win, Before the Devil Knows You’re Dead, Gone Baby Gone, Green Zone). Connie works as a salesperson for a mortuary, perhaps the world’s least-sexy job ever.

Though mutually reluctant, the two seem to hit it off (at least as much as they’ll allow themselves). Afterwards, on a walk home through snowy NY streets, the pair make stilted conversation. He clumsily invites her to go boating in Central Park, once spring arrives. She excitedly accepts. It’s not until after plans are made that he realizes he doesn't even know how to swim. But if it means winning Connie over, Jack’s willing to learn.

Later, after a mugging on the subway lands Connie in the hospital, Jack visits her. Though they still don’t know each other very well, she’s touched by his sweetness. He’s kind and genuine, qualities she’s not used to finding in men. He wants to cook her dinner, because she says no one’s ever done that for her before. Only he doesn’t know how to cook, either. Another skill to acquire.

The film’s second storyline is about Clyde and Lucy’s troubled relationship. They’ve suffered infidelity issues in the past which, as much as he wants to, Clyde’s unable to let go and get past. He copes by recreational drug use and alcohol. Because of this Lucy doesn’t respect him. There’s a smoldering distance between them, because of the emotionally injury that hasn’t healed. Seeing this, Jack becomes more doubtful about his chances with Connie. The eternal question: should he take the leap and risk rejection with Connie, or remain lonely in his safe, isolated little world?

This description may sound like not much happens. Perhaps not much does? But that’s not the point. The film’s about two couples: one struggling to gain its feet, the other struggling just to hang on. It captures perfectly the awkward silences and deafening nervousness between Jack and Connie, as well as the familiar fights between Lucy and Clyde. Like most people getting to know each other, Jack and Connie are at once hesitant, and overly-eager. Lucy and Clyde are familiar enough to know exactly where the other’s weak spots are.

Jack Goes Boating feels like a play. Most of it takes place in just a few places: tiny apartments, inside cars, hospital rooms. The action is in the dialogue and reactions of its actors. The small cast is pitch perfect, especially Hoffman. He struggles to hold it together hoping to impress Connie, despite his nervousness and insecurity. Each character has their particular quirks, charms and neuroses. The film won’t blow you away, but it's not trying to. What it does is leave a lasting sense of contentment and hope. It’s too bad the world won’t get to see more of the conspicuous talents Hoffman had to offer.