Jack Goes Boating, Philip Seymour Hoffman’s first time out directing a feature film, is such a gentle picture that at times it threatens to drift off the screen. Hoffman plays Jack, a going-nowhere, reggae-loving New York limo driver who appears never to have had a girlfriend. His closest friends, married couple Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega), decide to set him up with one of Lucy’s new co-workers, Connie (Amy Ryan) — she works phone sales for a slick funeral director-bereavement guru, though she’s so awkward and tentative in this new gig that she’s in danger of losing it.
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REVIEW: Philip Seymour Hoffman’s Jack Goes Boating Is Well-Crafted But Still Waterlogged