Before he won the Man Booker Prize, English novelist Howard Jacobson taught the works of William Shakespeare. The Bard also inspired his first book, the non-fiction work Shakespeare’s Magnanimity, about four of the playwright’s tragic heroes.

However, despite Jacobson’s love for Shakespeare, one work was left off his syllabi and went unmentioned in his writing: The Merchant of Venice.

“It was not a play that had ever figured largely in my imagination,” Jacobson says.

That may be a surprise for readers of Jacobson, who has written several fiction and non-fiction works with Jewish themes. Venice has remained one of Shakespeare’s most provocative works due to the character of Shylock, the moneylender that many argue is a Jewish caricature.

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Nevertheless, when publisher Hogarth enlisted various bestselling authors – including Jacobson, Margaret Atwood and Edward St. Aubyn – to reimagine Shakespeare’s works in contemporary times, he re-read the play and found it suitable for a new interpretation.

Fascinated by the character, Jacobson also agreed to appear in a BBC special about Shylock with Alan Yentob.

That documentary, Shylock’s Ghost, screens at the Toronto Jewish Film Festival on May 14, at Innis Town Hall.

Filmed last summer, the doc is an insightful and entertaining look into one of literature’s most controversial characters. In the film, Jacobson and Yentob visit Venice’s Jewish ghetto, where actors prepare to mark the area’s 500th anniversary with a new staging of Shakespeare’s play.

The timing was right for Jacobson, who was just finishing up Shylock Is My Name, his update of Venice, when he worked on the film. (That book is now available for purchase.)

Speaking to many distinguished scholars of the Bard, Jacobson admits that he thought of some new ideas for his novel inspired from their conversations.

“Of all the books I’ve ever written, I’ve never done one that kept changing itself [so much],” he says. “Shylock himself gets under your skin, and if you’re Jewish particularly, you feel differently about him every day.”

Shylock’s Ghost, directed by Colette Camden, features interviews with various actors who have played Shylock onstage, such as Dustin Hoffman and Antony Sher.

In other scenes, literary scholars debate whether or not the play is anti-Semitic. As the documentary explains, Shylock is considered “the most odious Jew literature ever spawned.” In the play, the moneylender demands to cut off a pound of Antonio’s flesh if the merchant cannot repay his loan.

Jacobson says he prefers actors that show off Shylock’s wit and strength. He is fond of English actor Henry Goodman’s take on the character, as well as Al Pacino’s depiction of Shylock in Michael Radford’s 2004 screen adaptation.

“I’m more taken by those actors who make you feel the maleness of Shylock,” he says. “The play is richer when we are alarmed by [him] actually, when we feel his power.”

Various literary scholars argue that Venice was taking the pulse of anti-Semitism during the time of its original staging. However, that play was performed 50 times in Nazi Germany between 1933 and 1939, perpetuating the propaganda of the time.

Nevertheless, Jacobson doesn’t see the play as anti-Semitic.

“People forget that these plays are plays – they are dramatic. At no point are you meant to take a side,” he says.

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Last year, a version of the play at Shakespeare’s Globe Theatre, added a scene with Shylock’s conversion to Christianity that wasn’t in the original text. A filming of that production, which features Jonathan Pryce as Shylock, will show at the Toronto Jewish Film Festival on May 15 at the Bloor Hot Docs Cinema.

After studying Venice so thoroughly for his novel, and taking part in the BBC documentary, Jacobson says that if given the opportunity to teach Shakespeare again, the play would be on his syllabus.

“The play’s been very badly read over the years,” he says, referring to the claims of anti-Semitism that clouds how people look at the text. “Shakespeare is too good a writer for us to read a play as simplistically as that.”