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HOW COLD WAS IT WHEN THEY shot night-time exteriors for “Jack Goes Boating” in New York City in February 2009?

“Sometimes it was too cold even for the snow machines to work,” said producer Peter Saraf.

“Next time you’re in the comfort of your home tapping out the words ‘NYC. Middle of the night. It’s snowing,’ hit delete and write ‘Bahamas. 70 degrees. Breezes blowing,’ ” he joked to scribe Bob Glaudini, who wrote the screenplay as well as the stage play from which it’s adapted.

“Boating” — a drama about working-class New York couples that combines friendship, love and betrayal — stars Philip Seymour Hoffman as the lead in an ensemble cast of four. It is also his film directing debut.

The bitter cold was one of several twists that unsettled production. Another was the fate of its distributor, Overture Films, which is being absorbed into Relativity Media even as the movie is being readied for its Sept. 17 release in New York and L.A.

Challenges also stemmed from Hoffman’s dual role as actor and helmer, and from his insistence on using an almost claustrophobically small interior space for the tiny New York apartment where much of the action takes place.

Hoffman is “a natural director and amazing with performers,” said Saraf, “but his (simultaneous) directing and starring had its own issues.”

“It’s tough when the director is an actor,” added d.p. Mott Hupfel. “Phil had to direct himself alongside the others. He can be very critical of himself at times, doing take after take and trying different things to make it better. It helped that Bob (Glaudini) was on the set to help judge the acting.”

The snow machines, when they worked, added to the difficulties. “They’re a nightmare, very noisy, and they drove Phil crazy because he hates looping,” said Hupfel. But in the end there was no solution other than to re-create the dialog of many of the outdoor scenes in the studio.

“Those were Phil’s hardest nights,” Hupfel said. “In addition to the noise, there were all the intimate scenes with Amy (Ryan); it was intense acting for him. Those are the times when you start feeling your low budget (Saraf pegs the budget at less than $7 million). You can’t light up the whole street, it’s 20 degrees and everything is pushed to the limit. Phil struggled hard to act and also direct really well.”

But Hupfel’s biggest challenge was shooting inside a tiny apartment constructed on a soundstage.

“Both Therese (DePrez, the production designer) and I argued to make it bigger, but Phil said no,” said Hupfel. “He had lived in an apartment like that right after he left NYU and wanted to replicate it. He was adamant that it be small.”

In order to properly light the cramped space and shoot inside it, the filmmakers devised walls that could be removed to accommodate the re-arrangement of lights and the movement of Hupfel’s 35mm camera on dolly tracks.

“It was really complicated,” he said. “We would often have to take down a whole side of the set. Our two weeks in that apartment was the hardest work of my career.”

Bookings & Signings

The Caleel Agency has booked producer Mark Cooper on Simon Curtis’ “My Week With Marilyn”; d.p.s Russell Carpenter on McG’s “This Means War,” Ross Emery on Kimble Rendall’s “Bait” and Yaron Levy on Michael Jai White’s “Never Back Down 2.” Agency has signed producer Ross Fanger (“A-Team”) and d.p. Matthew Lloyd (“April 86”).

Caleel has also hired Kristen Tolle, ex-head of Paradigm’s commercial department, to run its commercial division. She brings with her d.p.s David Claessen(“Diary of a Mad Black Woman”), Hisham Abed(“Secret Girlfriend”), Michael Pescasio (“David Knoll Finds His Soul”) and Eli Born(“Vacuum”); and production designers Ricardo Jattan (“The Perfect Host”) and Jennifer Dehghan (“Mr. Tambourine Man”). Tolle works alongside agent Louiza Vick, who joined Caleel earlier in the year, also from Paradigm.

peter.caranicas@variety.com

For earlier Bookings & Signings, and to read previous columns go to Variety.com/Caranicas