Jesse Eisenberg was 16 years old when he saw his first Woody Allen film, Crimes and Misdemeanors (1989), a plot riddled with murder, fate, and morality— all themes that recur in many of Allen’s films, including his latest, Café Society (in theaters today). Set in the 30's, the film follows Bobby (Eisenberg), who leaves his Polish immigrant family in Queens to pursue a career in Hollywood, hoping to follow in the footsteps of his powerhouse agent Uncle Phil (Steve Carrell). When Phil asks his assistant Vonnie (Kristen Stewart) to show his nephew the town, the two end up falling in love, even as Bobby is unaware that Vonnie and Phil are having an affair. And thus, another classic Allen trope—the love triangle—falls right into place. Here, the 31-year old actor and playwright, who is currently starring in a stage production he wrote (The Spoils) in London’s West End, discusses what it’s like working with Allen for the second time around.

Your character has so many expectations coming to Hollywood. Do you remember your first impressions? How do they hold up today? Despite my profession, I very infrequently go to Los Angeles—partly because they don’t film much in L.A. anymore, but also because I associate the city with nerve-wracking obligatory engagement. I think the first time I went out to L.A. was to screen test for a movie part I didn’t get, so I forever associate the city with this feeling of dread. In the movie, my character travels out there by train, optimistically looking to build a new life. But he becomes disgusted with what he sees as this shallow, backstabbing, ultimately unproductive and meaningless lifestyle.

So you can kind of relate to what your character went through when he arrived out there... Yes, but more specifically I can relate to his Polish family back in Queens, because my family went through what they did as well. In the 30's, my family, Jewish immigrants, was living in New York. Some members of my family—like in the movie—became Marxist intellectuals and teachers. Some of us worked in the nightclub scene, like my character does, and married outside of the religion. In the film, I married a statuesque blonde (Blake Lively) who was not part of my culture, my uncle is a Jewish Hollywood agent, and my brother is a gangster, which was all very much part of the Jewish reality during that time. A lot of the established industries during that time didn’t allow Jewish immigrants to enter. So I had family members who were brilliant and wanted to be doctors but became pharmacists because they were barred from entering other industries. So they went into entertainment. So it was the story as a whole that really resonated with me more than my personal experience going to Hollywood.

It’s wild how much your lineage relates to that of your character’s… Did Woody know this about you when he casted you? Woody had seen my plays, he saw one that took place in Poland (The Revisionist), so he knows my family history through my plays. Though I imagine my history is similar to anyone else’s who has a similar biography; I’m speaking for Jewish people from New York. This was a common experience for Jews in the 30's, who were escaping the things they were escaping from. One of the reasons why the movie industry was so dominated by Jews was because a lot of the other industries were restricted, but the movie industry was so new. It hadn’t been overtaken yet, so that allowed Jews to enter it.

Biographical similarities aside, what was it about your character, Bobby, that first spoke to you? I love anytime I can play a character that has two distinct sides, or a character that undergoes any kind of transition. So in this movie my character begins as this optimistic, naïve, sweet kid who goes out to Hollywood to try to get any job he possibly could. And by the end of the movie not only is he older, weary, a father, and married, but he’s kind of lamenting his past. He’s also a successful nightclub owner. It stays interesting for me because it allows me to explore how the same person can become someone so very different by the end, but when you look back it’s a transformation that seems gradual and likely.

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I felt his transformation was kind of tragic at the end. Even when he’s married, he still loves Vonnie, so he was forced into a different reality. I think the character grows cynical, which is not unsurprising given the movie was made by someone with a known public persona for having that worldview. The movie ends with the character not so much happy with their lives as they are but rather resigned to them, and although their circumstances are relatively good they’re actually stuck with the memories and loss of what could have been.

Do you share Woody’s cynicism? I think my writing is different because it has more to do with a generational divide than a philosophical one. I always think that Woody is presenting something authentic, given his worldview, which I find thoughtful, contemplative, and realistic, but I would say it’s less than optimistic. But I think that’s okay. I would much prefer to see something that he’s made that feels authentic than something less authentic but sunnier.

What was the best advice he gave you? Don’t make as many faces.

Meaning? We were doing a take and he told me to do the next take with less faces. I’d never been given acting direction like that before. He asks the actors to bring themselves to the roles, to improvise in their given circumstances, and fill in the gaps in the dialogue when there are long takes that require a scene to play out realistically. He gives the actors a lot of flexibility and free reign considering the fact that he’s such a thoughtful, exacting person. Because he films his movies in long single takes, they’re not going to be edited with a lot of different shots. When you do a play you do it in real time, whereas in movies it’s unusual. I like working that way, it makes it feel more realistic, as opposed to shooting a scene line by line and editing it together. He’s my favorite writer.

What was your favorite film of his growing up? Crimes and Misdemeanors. I thought it talked about all these wonderfully complicated philosophical ideas, but he cleverly disguised these sophisticated themes in a really compelling story. In the same movie, one story was more comedic, the other one more dramatic. I was 16 when I first saw it, I got into him a little later than you might expect, which people find surprising given my posture.

Meaning people often draw similarities between you two? Yeah, I write for The New Yorker, put on plays, so yeah, people make that association. I came to him later than a lot of people who end up enjoying him do.

What was the casting process like? He’s so brief and unpretentious, I met him for 30 seconds and he asked me to play a part in a movie a few years ago [To Rome With Love], and then for [Café Society] he sent me a note asking me to play a part. He’s so prolific that there’s not this long process where you’re hoping the script gets made in the next year. It’s quick, he’s brief. This film came out and he’s already in production on his next one.

Was there anything in particular you took away from working with him the second time around? He has a fixed idea of how things should sound, but once he’s on set he’s so flexible, more so than anyone I’ve ever seen. He has a sense that the scene can be done in a way that he envisioned it, but he’s open to the fact that what the actor is naturally doing might be superior to his vision of it, so in that way I think it’s actually a great lesson. I just directed something of my own, and I was able to relinquish the need for control and trust that the actors I had hired would do a better job with their role than my mind could have envisioned.

What was it like filming with Woody in Los Angeles? He’s not exactly known for his fondness for the city, but more for the line in Annie Hall: “The only cultural advantage is you can make a right turn on a red light…” The first few scenes we were filming were on the beach in Malibu, if you know anything about Woody Allen, it’s certainly surreal to be standing on a beach in Malibu with him. The image of him climbing over the rocks to stand on a beach in Malibu was surreal. I saw Malibu through his eyes.

Watch all the episodes of “The Myth of Orpheus and Eurydice,” a four-part film series by Gia Coppola, here. Produced for Gucci by W magazine.