With Bored to Death, Rushmore and The Darjeeling Limited, Jason Schwartzman has forged a niche for playing neurotic writers. But with Listen Up Philip, the latest from writer-director Alex Ross Perry, there's a new tweak to this niche. "Those writers that I’ve played before would be jealous of this one, " Schwartzman told me as we sat down in a Tribeca office to discuss the New York Film Festival selection, "because he actually has published two books and he’s pretty well regarded."

Listen Up Philip stars Jason Schwartzman as Philip Lewis Friedman, a novelist who has opportunity knocking, has his literary idol as a mentor, and is essentially his own worst enemy. He refuses to promote his novel. He sabotages writing assignments that could bring him wealth and further recognition. And maybe most impactful, he pushes away those who would dare to love him, like his photographer girlfriend Ashley Kane, played by Elisabeth Moss.

Elisabeth Moss and Jason Schwartzman have known each other for years, as both grew up in Los Angeles. Yet despite bustling careers in film and television, Listen Up Philip marks the first time they've ever worked together. I asked if their friendship and familiarity with each other made it easier to dig into the caustic arguments of their characters in the film. Moss responded:
Yeah, for sure. I mean, Jason’s the sweetest, most awesome guy. He’s so funny and smart, and lovely. I think it helped that we have known each other for so long because in the film, we drop in to close to the end of their relationship really. So you don’t have a lot of time to kind of develop a rapport or develop an ease or any of those kinds of things. We didn’t have time to do that. So, it definitely helped that we didn’t have to get to know each other. We’re fine. We know each other. We don’t have to do all of that, and we have kind of a natural chemistry which definitely I think really helped us."

Schwartzman reminisced about teen Lizzy Moss before explaining how this helped with Listen Up Philip:
"We used to hang out when I was in this band. Back then she was 16 and she was always so sweet and nice, and I think just knowing the type of person she was, like the fact that she would like wear these cute dresses she had. She has a cute necklace with her name on it. I think it said like 'Moss' or 'Lizzy.' She was just nice and great. So when Alex said, 'Yeah, I think Elizabeth Moss is going to do it,' I was like, 'Oh, I hadn’t seen her for years, but there’s no question she’s a great actor.'

But what I remembered of Elisabeth was that she was great and you know, nothing has changed…It’s not like I knew her super well, but if it was like a brand new actress that I had to work against, opposite, be in love with, be out of love with, I think there would have been a lot more, like extra fabric, to have to like hem. Because we would have been like nervous. I would have been nervous probably and made bad jokes, and then like calling Alex after, 'I think I made too many bad jokes.' 'No, no, its fine. She thinks you’re great.' 'I feel like I shouldn’t have said the thing about the smoothie.' 'No, no, it was good, it was funny! Everyone has smoothies.' That would have happened. But, because it was her, it was like hey, how are you, good to see you. There was just like an instant familiarity."

Check out a clip of Schwartzman and Moss arguing in Listen Up Philip:

For more on Schwartzman's thoughts on Listen Up Philip, Walk Hard and the possibility of a Rushmore sequel and his hopes for Star Wars: Episode VII, click to page 2. For more from Elisabeth Moss, including details on her reunion with Listen Up Philip's writer-director, Queen of Earth, click to page three.

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