Oscar winner Philip Seymour Hoffman (who was found dead in his New York City apartment on Feb. 2, 2014) was a respected and highly accomplished actor, but he was just getting started in directing movies. His feature-film debut was an adaptation of the off-Broadway play “Jack Goes Boating.” Hoffman co-starred in the “Jack Goes Boating” movie (released in 2010) with John Ortiz, Daphne Rubin-Vega, who were both in the play with him. “Jack Goes Boating” would turn out to be the first and last movie that Hoffman directed. A few days before his untimely death, it was announced that Hoffman was going to direct the movie "Ezekiel Moss."
“Jack Goes Boating” tells the story of four New Yorkers who share common bonds through work and through love. Jack is a lonely limo driver whose closest relationship is with his best friend/co-worker Clyde (played by Ortiz, one of the executive producers of the film). Clyde is in a crumbling marriage to Lucy (played by Rubin-Vega), who works at a funeral home. Clyde and Lucy play matchmaker and introduce Jack to Lucy's single co-worker Connie (played by Amy Ryan), who has intimacy issues. Connie and Jack begin dating, and they tentatively become a couple. (Beth Cole was Connie in the “Jack Goes Boating” play.)
When Connie mentions to Jack that she would like to go boating with him in Central Park, Jack (who doesn’t know how to swim) decides to get swimming lessons from Clyde. Jack also plans to impress Connie by cooking for a dinner party held at Clyde and Lucy’s home. That dinner party serves as a catalyst for true feelings that are revealed, and it is a test of where each couple’s relationship is headed. At the 2013 First Time Festival in New York City (a film festival featuring movies from first-time directors) Hoffman did a Q&A following a screening of “Jack Goes Boating.” Here is what he said.
Can you talk about why you wanted “Jack Goes Boating” to be the first movie that you directed?
Hoffman: It was a play that I did with John Ortiz, who plays Clyde, at the LAByrinth Theater Company. I had directed a few plays at that point. This was first play that John and I acted in. I didn’t direct the play. Peter DuBois did. Amy was in a different play but joined us on the film later, which was really exciting.
The play did very well. It ran for three months, which is a long time for an off-Broadway gig. And then Peter Saraf at Big Beach approached us about making it into a film. We started thinking it about that way, and then John Ortiz approached me about directing the film, because I had been directing theater for 10 years at that point. So it was the next chronological step.