Uploaded July 2010 | Updated September 2026, 1 hour ago
In Philip Seymore Hoffman's directorial debut, Jack Goes Boating is an unconventional romantic comedy set in the midst of working-class New York City life. In the dead of winter, we meet Jack (Philip Seymore Hoffman of CAPOTE), a limo driver who has vague dreams of landing a job with the MTA, a mild obsession with a reggae song, and has begun a half-hearted attempt at growing dreadlocks. He spends most of his time hanging out with his best friend and fellow driver, Clyde (John Ortiz of PRIDE AND GLORY) and Clyde's wife Lucy (Daphne Rubin-Vega of Broadway's RENT). After being set up with the couple's friend Connie (Amy Ryan of GONE BABY GONE), Jack is inspired to learn to cook, pursue a new career, and take swimming lessons from Clyde so he can give Connie the romantic boat ride she has always wanted. But as Jack and Connie cautiously circle commitment, Clyde and Lucy's marriage begins to disintegrate. From there, we watch as each couple must come face to face with the inevitable path of their relationship.
In Philip Seymore Hoffman's directorial debut, Jack Goes Boating is an unconventional romantic comedy set in the midst of working-class New York City life. In the dead of winter, we meet Jack (Philip Seymore Hoffman of CAPOTE), a limo driver who has vague dreams of landing a job with the MTA, a mild obsession with a reggae song, and has begun a half-hearted attempt at growing dreadlocks. He spends most of his time hanging out with his best friend and fellow driver, Clyde (John Ortiz of PRIDE AND GLORY) and Clyde's wife Lucy (Daphne Rubin-Vega of Broadway's RENT). After being set up with the couple's friend Connie (Amy Ryan of GONE BABY GONE), Jack is inspired to learn to cook, pursue a new career, and take swimming lessons from Clyde so he can give Connie the romantic boat ride she has always wanted. But as Jack and Connie cautiously circle commitment, Clyde and Lucy's marriage begins to disintegrate. From there, we watch as each couple must come face to face with the inevitable path of their relationship.
