Jessie Kahnweiler’s bubbe died and left her a lot of money, but she can’t get it unless she “lives Jewish” for a year. Well, not really, but this is the conceit of “Dude, Where’s My Chutzpah?”— a new comedic documentary web series chronicling the young filmmaker’s recent journey into the wide and deep world of Jewish tradition and expression. The payoff involves no cash, but a better understanding of Kahnweiler’s own spirituality and Jewish identity instead.

The 11-part series has a movie-within-a-movie kind of feel (think Sacha Baron Cohen in “Borat”), and Kahnweiler plays a character that is a riff on her real persona. “It’s me, but with better clothes,” she quipped in a phone conversation with The Times of Israel.

The series, which kicks off this week with a launch party at the Downtown Independent Theater in Los Angeles on Sunday, is Kahnweiler’s Six Points Fellowship project. She is a member of the first Los Angeles cohort of the UJA-Federation-sponsored fellowship program for artists creating new work that explores Jewish ideas and experience.

“This is not your Birthright Israel promo video,” Kahnweiler, 28, warned about her edgy series, which takes her from Los Angeles to Israel and back, searching for God, discovering Israel and Palestine, healing the world and looking for love. Along the way she meets a plethora of people who share with her their version of Judaism, while putting up with her humorous schtick.

She actually did go on a Birthright Israel trip four years. “It could have been a trip to China for all I cared,” she said. “It was a free trip. It certainly did not make me want to claim my Judaism.”

‘This is not your Birthright Israel promo video’

Raised in an affiliated Reform in Atlanta, Kahnweiler hadn’t thought about getting more in touch with her Jewish identity as she worked various jobs in production, casting and editorial in Hollywood following her graduation from University of Redlands, where she studied liberal arts and began filmmaking (her senior thesis was a film about truck drivers, for which she hitchhiked across the country—something she did not tell her mother about until after it was done).

One of her mentors, Emmy-nominated television writer and award-winning film director Jill Soloway, suggested she apply for the Six Points Fellowship. “I figured, why not?” Kahnweiler recalled. “But then when I found out my proposed project had to be about something Jewish, I panicked.”

Not sure what her Jewish identity was, or what it meant to be Jewish for someone who, like her, was not particularly spiritual, she decided to go out and seek answers — and to bring her audience along.

“I thought it was going to be more of a surface kind of thing, more about providing information, but it ended up becoming this combination between a documentary and a narrative comedy,” she said.

‘What is Israel and why should I give a shit about it?’

She found that the key to developing herself as a Jewish person, as well as her film project, was authentic experience. “In both my work and my personal life, it’s always about relationships,” she explained. For instance, she spent a month in Israel in the summer of 2012 nowhere near a tour bus, spending time with and getting to know everyday Israelis in an attempt to answer questions like, “What is Israel and why should I give a shit about it?” and “Does Israel care about me?”

She also figured it was worth crossing the Green Line and spending a day in Palestine. “I went in with a naïveté. I was amazed to find Israelis who were inside Palestine protesting against the security wall and the settlers. That’s not something most young American Jews know about,” she said.

“We got tear gassed. We got caught in the crossfire. I spoke to soldiers and to Palestinians. I didn’t get any definitive answers, but I will forever see things differently now. It really rocked my world.”

While she aims to entertain with “Dude, Where’s My Chutzpah?” (The title being an obvious riff on “Dude, Where’s My Car?”), the year of research and preparation she did before commencing filming was no joke. She interviewed over 25 rabbis in Los Angeles, having first studied up on midrash, kabbalah, and Jewish and Israeli history and culture in classes at the American Jewish University and IKAR, a progressive, egalitarian Jewish community led by Rabbi Sharon Brous, considered to be one of the most influential rabbis in the United States.

With a view to picking up some Yiddish culture, she volunteered at the Los Angeles Jewish Home, and she also studied privately with an Aish rabbi.

‘I realized that Judaism is radical, it’s sexy, it’s creative’

“I play a character that is a version of me, and the series is very much a character arc, one that moves from apathy to a deep caring,” Kahnweiler reflected. “I realized that Judaism is radical, it’s sexy, it’s creative — which is the opposite of what I thought it would be.”

What she thought it would be was informed by her not atypical “very Reform” upbringing. She went to a temple-based religious school until her bat mitzvah, but did not continue her Jewish education after that. She liked getting together with family for holiday meals, but never sought to be pro-actively Jewish or to make Jewish friends or date Jewish guys. “It was what I call ‘defensive Judaism,’” she said.

“I saw it as my grandparents’ religion, not mine. I never felt I had a personal relationship to it, and I never understood why I should believe or do the traditions.”

Until Kahnweiler embarked on “Dude,” she had a take-it-or-leave-it attitude to her religion, which she doesn’t find surprising, given that her strongest memory from prayer services was her father teaching her how to count the tiles on the synagogue’s ceiling.

Jessie Kahnweiler, left, trying to blend in in a religious neighborhood of Jerusalem. (photo credit: courtesy of Jessie Kahnweiler)

Jessie Kahnweiler, left, trying to blend in in a religious neighborhood of Jerusalem. (photo credit: courtesy of Jessie Kahnweiler)

Now, she feels she can tap into Judaism in a myriad of ways. Just a couple of weeks ago she spent Shabbat at the home of an Orthodox family, and it didn’t feel weird. “I’m so comfortable in the grey now,” she said. “Labels aren’t important to me anymore when it comes to being Jewish. No example of Judaism is wrong. Judaism is what you want it to be.”

The filmmaker is excited about how Judaism and Israel are coming into her life in a natural, organic way. “For instance, I am so into Israeli music now. I’m using it in a new film I’m working on that has nothing to do with Israel.”

At the same time, she doesn’t minimize the difficulties she encountered. “I took it on full force. It was an overwhelming, frustrating and scary process,” she shared.

While she says she is not yet in the headspace to think about having children, she does know that she would want them to have the opportunity to understand that Judaism is an incredible culture, tradition and heritage. “It’s a culture I’m really proud to be part of,” she said.

However, she’s not yet convinced that her life’s partner should be a Jew. “I want to date a mensch, but he doesn’t necessarily have to be Jewish.”

The series, which Kahnweiler financed through the fellowship and a Jewcer.com crowdsourcing campaign, can be viewed on her YouTube channel. Three episodes will be released per week, with the entire series unfolding over the course of the upcoming month.

‘I want to date a mensch, but he doesn’t necessarily have to be Jewish’

She’s not completely sure who the target audience for “Dude” is, though she presumes it will be unaffiliated young Jews, non-Jews interested in Judaism but worried they don’t know what questions to ask, and people interested in Israel.

No doubt, Kahnweiler is hoping for many viewers in the end, but what this project has ultimately been about is the journey. “It’s been about reclaiming my chutzpah, something which has traditionally had negative connotations. What I’m talking about is holy chutzpah — about standing up, questioning and challenging parts of myself.”