Bob Glaudini
“If I outline [a script] and I know it all, I’m less interested in writing it. [Writing] is something I want to discover.”
The Deep End
Playwright-screenwriter Bob Glaudini emerges from a dark place to tell a story about hope and peril on the sea of love, the Phillip Seymour Hoffman-directed romantic dramedy Jack Goes Boating.

Written by Dylan Callaghan

The new romantic dramedy Jack Goes Boating came, as much good art does, out of nasty pain. Playwright Bob Glaudini, a member of the LAByrinth Theater Company in New York with Oscar-winning actor and Jack Goes Boating director Phillip Seymour Hoffman, had gone through some relationship agonies of a fairly brutal variety. Specifics aren’t needed, but as Glaudini was set to write what he was sure would be a dark, cynical screed on human relationships, the veteran stage and film actor, whose nearly four-decade film career has included smaller parts in Bugsy and The Princess Diaries, says he “could not deny that what I was seeing around me was people being kind to each other.” His ugly existential despair was essentially being messed up by human kindness. So he went with it.

The result was a well-received play telling a poetically bifurcated tale of a troubled couple, Clyde and Lucy (played by LAB members John Ortiz and Daphne Rubin-Vega), who, even as their relationship hits rough seas, are compelled to help loveable stoner/lonely heart Jack (Hoffman) embark on his own awkward path to love with an equally socially off-kilter mate, Connie (Amy Ryan). Jack can’t swim, but Clyde teaches him so that, no matter what becomes of his own foundering relationship, Jack can take his new sweetheart on a promised boat ride.

It is romantic dramedy with floaties – a central metaphor for the terror and anxiety of beginning a relationship and of ending one.

Glaudini talked to the Writers Guild of America, West Web site about the play’s inception, his organic writing style, and how he and Hoffman worked together to shape the play’s adaptation to the big screen.

When writing this play originally, were you cognizant of how it could work as a film?

Yes, and I’ll tell you why. I’m a member of this group LAByrinth Theater Company [with] Phil [Hoffman] and John Ortiz and Daphne [Rubin-Vega] and every summer there’s a retreat – we call it the Intensive – up in Vermont, and there’s a lake up there. I didn’t have a play at the time, and I thought, maybe I’ll go up and write some scenes and we’ll just do some digital shooting, to open up that little avenue.

Photo: ©2010 Overture Films
Philip Seymour Hoffman and Amy Ryan in Jack Goes Boating.

I imagined this lake, and I started thinking about someone teaching someone to swim. Then when I started writing it, it just turned into a play. But I was always aware of it in terms of its cinematic quality... When we produced it [for the stage], Peter Dubois, the director of the play and I talked about the cinematic scene changes and so forth. So it’s always been part of its development.

And from that inception of the lake and the idea of someone teaching someone to swim, where did the whole narrative of these two timid lonely hearts juxtaposed with this married couple come from?

I don’t know how much of this should be revealed, because really it’s just about the work itself, but you can decide. At that time, when I started writing it, after this image of someone helping someone learn how to swim, I was kind of drawing upon a devastating personal break up with betrayal and all that. I thought I was going to write the most cynical, bitter, vicious piece I could imagine, but at the same time, even in this depressive state, I couldn’t deny that what I was seeing around me was people being kind to each other, you know?

So that kind of hope started blossoming. I was writing, I think, about the terror and anxiety of both things – of something breaking up and of something beginning.

I’m not very schematic in terms of how I write, so I just followed the characters. The Jack and Connie characters wouldn’t let me stay totally cynical. It developed organically that way.

What do you write with? Pen and paper? A computer?

Both, pen and paper, but eventually the computer takes over.

But as far as the actual script, you don’t outline?

No, but hopefully I get an image or something that draws me towards it. Not necessarily the ending, but when I’m lucky, there’s a strong image that I feel is drawing me toward it. It might not be concrete, but I will recognize various motifs in that and will be drawn toward those.

This is an interesting thing that keeps coming up with all the screenwriters I’ve spoken with, the planned script versus the organic script. For you, what is creatively important about not outlining and about letting the characters lead you?  

I think discovering what I don’t know and being surprised by the various turns of the journey, as opposed to fitting it to pre-conceived beats or outlines. You’ve probably heard this before. There are at least two schools on it and one is, if I outline it and I know it all, I’m less interested in writing it. [Writing] is something I want to discover. You hear that cut both ways. I’m not against the idea [of outlining]. I’m working on an idea for a television show now with another writer, and that is completely different – we’re trying to map out the whole 10 episodes. But when I just write on my own, I don’t do that. When the medium calls for it, I’m gonna do it, but not when I’m left to my own devices.

Was Jack Goes Boating an easy write? What was the biggest challenge about the play and the screen adaptation?

It’s been a while since I wrote the play, but it wrote pretty quickly. I would go back and rewrite it, but it took five or six weeks, maybe even less. The difficulty with this play was going back and scaling it down. It was kind of elliptical, and there’s no plot really. The rewriting is a constant process from the beginning through rehearsals, and then there’s nothing you can do about it.

How easily did it adapt to a screenplay?

I knew Phil was going to direct it, so it was an organic evolution there, too. Phil and I would talk. As he was coming to know his ideas for filming it, I was writing the draft, so we would meet and talk, and he would tell me his vision for the film and that fed into the writing of the screenplay. I was very happy to give the director what he wanted. He had strong notions of what he didn’t want to do. He didn’t want to just take it away from the play, he wanted to stay close to that.

It brings to mind Paddy Chayefsky's award-winning 1950s teleplay and later screenplay, Marty. Did you have that in mind?

It didn’t dawn on me while writing it, but I’ve had a couple of other characters I’ve written in other works that I think you could say that about too… I don’t disavow that at all.

When you first screened the film, did it surprise you in any way?

Well, I was involved during the whole filming. I was on set every day. But I was very pleased when it was screened at Sundance – and granted they are eager film fans – but it was really rewarding to see what played, and what could have been done better. It’s not a perfect work, by any means, but I’m really proud of the film.