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John Turturro Fading GigoloJOJO WHILDEN

Whether you like the movies that John Turturro directs, you have to admit one thing: He is not risk-averse. He goes for it.

As an actor, Turturro, 57, can be handsome or squirrelly; his burning eyes can look menacing or dignified. So he's at home in every kind of picture, be it blockbuster or comedy, indie or art house. He's appeared in films by Francesco Rosi, Nanni Moretti and Sally Potter, plus four films for the Coen brothers, nine for Spike Lee, three Adam Sandler capers and three Transformers movies.

As a director, his choices are frankly eccentric. He has been at the helm of a drama about intrigue at an early-1900s European theatre company (Illuminata), a musical about infidelity starring James Gandolfini and Kate Winslet (Romance and Cigarettes) and a compilation of performances tracing the musical history of Naples, Italy, (Passione). (There's a live number in the middle of that last one that will blow your ears off. I saw it at a 10 p.m. TIFF screening that was by no means full, but when that song ended everyone burst into applause.)

Turturro's most recent outing as writer/director/actor, which opened in select cities on Friday, is Fading Gigolo, a sad-eyed comedy about an antiquarian bookstore-owner turned pimp named Murray (Woody Allen) who persuades his friend Fioravante (Turturro) to sleep with rich women for money. It's a fable – do you know how you can tell? The rich women are played by Sharon Stone and Sofia Vergara, and Vanessa Paradis (the French model/singer/actress and ex-Mrs. Johnny Depp) steals the show as a Hasidic widow. The whole thing is patently absurd, but Turturro is so sincere, and his depiction of New York so nostalgic and neighbourhoody, that you forgive him.

"If you're going to take a chance and make a movie, why not take a chance?" he asked in a recent phone interview. "I don't want to make a movie that I've seen a hundred times. The movies that I love, you go: 'Wow, I've never seen anything like this.' Yet, they resonate with you in some way. I know that the filmmakers really shared something with me. Bunuel, Truffaut. Shampoo, Midnight Cowboy, Nights of Cabiria. I could go on and on."

You can hear Turturro's native Brooklyn in his voice – not hipster Brooklyn, but old-school borough. (His mother was a Sicilian-born amateur jazz singer; his father, an Italian-born carpenter and construction worker.) Turturro is old-world in his manner, too, courtly and encouraging. When I interviewed him and three of his colleagues in Toronto a few years ago, my foot got caught in the strap of my bag as I rose to leave, and I collapsed back in my chair. I would have stumbled on purpose, had I known what cries of concern and solicitous soothing it would elicit.

Fading Gigolo began with Turturro's instinct that he and Allen would have chemistry on screen. "And I think we do," he says now. They'd first worked together in Allen's 1986 film Hannah and Her Sisters; more recently, they did a one-act play together on Broadway. Their characters' mentor/protégé relationship carried over off-screen, too. "Woody encouraged me to develop the story in a nuanced way, and to try to make it human," Turturro says. "He made me believe that the film could start out with this crazy idea, but still be delicate, and go somewhere serious."

Allen has said that other directors rarely hire him to act, but Turturro praises him as a pro – on time, knows his lines, contributes helpful improv. (Amusingly, Allen didn't know who Paradis was. "He really thought she was a Hasidic woman," Turturro says.)

Turturro did a lot of research on the Hasidic community – he thought a religious obstacle would be interesting to explore in a movie about sex – as well as prostitution. He's long been fascinated by movies about streetwalkers, he says. "Because sometimes there's an emotional nakedness within the transaction. I was interested in – not to sound pretentious – the therapeutic aspect in some of these encounters, where people are trying to deal with grief or loss or loneliness, or an escape from their life. Maybe they don't know how to do something, or ask for something. There's a lot that goes on. Not just physically."

A music fiend, Turturro always writes to particular songs; for this script, his favourites included the French singer Dalida, the saxophonist Gene Ammons, and the jazz standard Canadian Sunset. "Sometimes, there's something contrapuntal going on, like the soul of a song," he says. "It puts you in this nice receiving mood, without telling you exactly how to feel." He played the same songs during the shoot, and they also ended up on the soundtrack.

Turturro's directing style was all about getting his cast to relax. "My character is a good listener, and I also was interested in hearing the actors' points of view. As an actor, you can always tell if your director is involved in the look of the character with you, the costumes, the set design, the small details. Those things can be instrumental in freeing someone, or in unmasking someone."

Mainly, he didn't want anyone to push: "I told Sharon and Sofia: 'Let yourself be as delicate as possible. You don't have to sell it.' I didn't want a surface sexuality. It could be funny, but not over the top."

Still, I nudge him – three of the most gorgeous women on the planet, paying for sex? I can hear him grin. "The plot of the movie is about economic choices, and when you cast a movie it's about economic choices, too," he replies. "You need to get your film financed." But he also believes casting beautiful actresses makes a legitimate point: "You can have a relationship, you can be rich, and you can still be empty. People can be lonely in all different ways."

Turturro feels this is a rich time in his life – if he can navigate it properly. He has a lot of ideas he'd like to try, and he's more relaxed about trying them. "That doesn't make it easier, though," he admits, chuckling. "You have to be a little braver now to go outside of the mainstream. But I think people have a big appetite for things that do. Everything can't be CGI. And when the risk works, it makes everybody happy.

"Isn't that why you go to the movies?" he asks. "To be taken some place new?"

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