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A scene from “Confessions of a Self-Hating Jew”

Phillip Roth describes it as one of the most striking moments of his childhood. It was 1978, and the 12-year-old film buff was watching the Academy Award ceremonies on television when Vanessa Redgrave denounced "Zionist hoodlums" while accepting her Oscar for best supporting actress.

"That speech had a huge impact on me," says Roth, a Los Angeles-based filmmaker (who is no relation to the novelist). "It was probably the first time I realized that there were people out there, besides terrorists, who were really critical of Israel." Redgrave's memorable speech was met with boos and hisses at the ceremony, and one standing ovation – from her Julia co-star, Jane Fonda.

Roth, who was brought up in a Jewish household in L.A., says that issues surrounding the American Jewish community's relationship to Israel continued to fascinate him – one in particular. "American Jews really aren't allowed to say anything critical about Israel," he contends. "If you look at the Israeli press, there is a vigorous debate, one that goes on constantly. Israelis are allowed to be very critical of Israel. Americans, it seems, are not. Among my friends and family, I would find people who were very liberal on every issue imaginable, except when it came to Israel and the Middle East."

Adds Roth, "When the subject arrived at Israel, it was almost like the conversation was cut off."

That observation prompted Roth to make his own first-person documentary on the subject; the result is a heady mix of the personal and political. Confessions of a Self-Hating Jew, which has its world premiere this weekend at the Montreal World Film Festival, features Roth's journey to come to grips with the complex bundle of personal, political and historical connections that the Jewish diaspora has with the nation state of Israel.

Roth interviewed a broad range of people for his documentary – from his own grandmother to Phyllis Chesler, author of The New Anti-Semitism, in which she warns of a dangerous rise in anti-Jewish prejudice in the early 21st century. The results are fascinating, with Roth careful to give plenty of time to those he clearly disagrees with.

He acknowledges that some have criticized him for taking on such a project. "I'm a gay man who teaches naked yoga classes in Los Angeles. I've never been to the Middle East. But I really liked the idea of someone like me, clearly a non-expert, taking on these questions and asking them, very bluntly. After all, two-thirds of American Jews have never been to Israel. But if we question our government's ties to and support of Israel, we are branded as being self-hating."

As Roth researched Confessions of a Self-Hating Jew – which he calls "a five-year labour of love" – he found particular kinship in one of the historical figures whose story he recounts. "Hannah Arendt, herself a survivor of the Nazi camps, wrote quite critically of Zionism after the trial of Adolf Eichmann. She was then accused of being self-hating, simply because she argued that the original vision of Zionism had gone astray."

By the film's end, Roth finds himself advocating for a version of the controversial one-state solution, in which Israelis and Palestinians would live in the same country; one-person, one-vote. One of his interview subjects contests the idea strongly, saying such a system would mean "national suicide for Israel."

Argues Roth, "As long as you have so many Jewish settlements in the West Bank, as long as you're giving Americans and Russians and other immigrants so many financial incentives to live there, and as long as you then also have impoverished Palestinians living alongside them, I think you've got to give those Palestinians equal citizenship. I'm sorry, but if you don't, then it really is like apartheid."

And he concedes there is a certain irony in having Confessions of a Self-Hating Jew see its world premiere in Canada, whose Conservative government has emerged as a staunch defender of Israel.

"I don't pretend that Zionists are going to walk into the cinema and have their minds changed by my film," Roth says. "But we have to talk about this. These policies of building new settlements in the West Bank: Are they really helping Israel? Haven't they just created an impossible situation?"