Jack (Philip Seymour Hoffman) works for his uncle, who owns a limousine company run out of a trailer on the Brooklyn side of the East River. His friend Clyde (John Ortiz) also drives a limo, and Clyde's wife Lucy (Daphne Rubin-Vega) sells seminars to grieving family members for a mortician named Dr. Bob. Like an awkward overgrown teenage son, unable to fend for himself and perpetually clad in a knit cap, Jack leans on Clyde and Lucy for stability in a world filled with looming dangers—swimming, cooking, dating. When things get overwhelming, he dons his headphones and grooves to Bob Marley's "Rivers of Babylon." When life overwhelms Lucy and Clyde, they—like some parents—turn to less innocent ways to cope with their own disillusionment. They're beginning to realize that their big plans will probably never happen. Their railroad apartment and mediocre jobs constitute their life—for better, or more probably, for worse.

Jack is lovable, in his helpless way, and knowing he'll need a nudge to find a soul mate, Clyde and Lucy decide to set him up with Lucy's coworker Connie (Amy Ryan), who is sweet, naive, and vulnerable to a fault. Both Connie and Jack know they are misfits—they're smart, even articulate, but missed the day the map for navigating life was handed out.

Philip Seymour Hoffman as Jack

Philip Seymour Hoffman as Jack

Still, Jack and Connie hit it off over dinner at Clyde and Lucy's place—each displays deal-breaking social awkwardness (Connie leads off with the tragic story of her father's death), but their mutual discomfort draws them together. As they walk to the curb in the snow, Connie mentions to Jack that she's always wanted to go boating, and perhaps they might go together when the weather becomes warmer. Jack agrees, delighted at her implied confidence in the longevity of the budding relationship, but has one problem: he doesn't know how to swim.

Clyde once taught Lucy to swim, and offers to teach Jack. Their friendship deepens in the water and over coffee, and one night, Clyde shares his secret heartbreak with Jack: Lucy had an affair years ago with a chef he calls "The Cannoli," who, incidentally, would be happy to help Jack learn to cook for Connie. Despite Clyde's protestations that everything is okay now, Jack's world is shaken—Lucy and Clyde's relationship is all he has, and it embodies everything he knows to be true. How will he proceed with Connie, whose presence in his life awakens his protective instinct, when his model of love is falling apart before his eyes?

Amy Ryan as Connie

Amy Ryan as Connie

Jack Goes Boating began life as a stage play written by Bob Glaudini and workshopped by New York's LAByrinth Theater Company, where Hoffman and Ortiz were co-artistic directors until recently. After a successful run, the company continued to workshop the play, developing it into this screenplay (also written by Glaudini). LAByrinth's deliberate, extended work on the story makes the film more richly developed than the play. Dialogue has been smoothed; relationships have been expanded; characters have been tweaked to more closely resemble, well, us.

Three of the four original cast members their roles for the film, where they were joined by Ryan. Their shared history mirrors the story—Jack, Lucy, and Clyde have a history that is shaken up by newcomer Connie—and is reflected in their easy chemistry with one another, particularly between Hoffman and Ortiz, whose pain-laced friendship sometimes blurs the who-needs-whom line. Ryan's Connie is especially understated and believable, even in her occasional oddness.

Daphne Rubin-Vega as Lucy

Daphne Rubin-Vega as Lucy

This is Hoffman's screen directorial debut, and his hand is sure and steady—not surprising, given his own performances. The tone is quirky: intense and serious, first digging the knife in and then laughing at its own pain. Yet it's not perfect. The story still bears the stamp of the play, occasionally getting trapped inside a room like a stage. And though we can't help but love Jack and Connie, their occasional weirdness can distance them from us even though we want to root for them.

The adults-acting-badly genre is popular in the art-house scene—Noah Baumbach (The Squid and the Whale) perhaps being its king—but despite its wincing moments, Jack Goes Boating has a much sweeter heart than its darker cousins. Each couple is floundering toward maturity, discovering what the next stage of love looks like for them. In drugs, alcohol, and other people, Clyde and Lucy are trying to regain the sense of wonder and intimacy they once found in idealizing one another, but lost when each turned out to be disappointingly mundane. By contrast, Jack and Connie—each aware of and even content in their ordinariness—find in one another healing for their deficiencies, matching strengths to cover their own weaknesses even as they grow and mature.

A grey, snowy winter turns to spring; uncertainty blossoms into confidence. "I knew you'd be good," Connie tells Jack.

"I am, for you," he replies.

Talk About It

  1. What is each character searching for? Where are they finding it? Have you ever looked for fulfillment in something, only to find out it didn't last?
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  1. Both Connie and Jack feel out of place in their world. Have you ever felt as if something about you would keep others from loving you? What did you do?
  2. Do you think Clyde and Lucy have a chance? Why? And what about Jack and Connie?

The Family Corner

Jack Goes Boating is rated R for language, drug use, and some sexual content. Hashish and cocaine make an appearance at a dinner party. Profanities and obscenities are sprinkled throughout. Several characters speak bluntly their sexual affairs. A character is assaulted on the subway—off camera, but we see the result and hear the story in some detail. Two characters discuss their inability to be sexually intimate; one begs the other to "overcome" her; there are several bed scenes but everyone is clothed.

Jack Goes Boating
Our Rating
3 Stars - Good
Average Rating
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Mpaa Rating
R (for language, drug use, and some sexual content)
Directed By
Philip Seymour Hoffman
Run Time
1 hour 29 minutes
Philip Seymour Hoffman, Amy Ryan, John Ortiz
Theatre Release
December 29, 2010 by Overture Films
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