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Although he's known throughout the world as a jazz pianist, Herbie Hancock started out playing classical music. In fact, he was a bit of prodigy, winning a competition at age 11 to perform a Mozart concerto with the Chicago Symphony.

"Actually, I didn't do any solo recitals," he recalls. "When my teacher had a recital for her students, I would play one or maybe two pieces, and then some other students of hers would play some other pieces. But the first time I was a soloist was when I was 11."

"I started off as an engineering major in college, for two years," he continues, over the phone from his office in Los Angeles. "But then I changed to music composition for my third and fourth year, and I got my degree in music. But after that, I really stopped having a formal relationship with classical music."

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Instead, he became one of the hottest young pianists in jazz, cutting his first album, Takin' Off, in 1962 (it included his classic composition Watermelon Man), and joining the Miles Davis quintet a year later. Over the next few decades, Hancock did a bit of everything, from soundtrack work to electronic funk to Brazilian pop, and in 2008 won the album of the year Grammy Award for his Joni Mitchell tribute, River: The Joni Letters.

That same year, classical music popped back into his life. He had been asked to do a truncated version of George Gershwin's Rhapsody in Blue as a duet with the classical pianist Lang Lang. "That was initially just a one-time thing, but it led to six concerts in Europe, and a few in the United States and Canada," he says. "Classical music kept popping up in different forms, and so I began to see it as kind of a sign, a new opportunity presenting itself to me as a professional now.

"So now I'm exploring that territory."

That's why, when he comes to Toronto's Massey Hall on Saturday, he'll be performing with an orchestra, not a jazz band. And even though he'll be performing Rhapsody in Blue again, he won't be playing it the way he did with Lang Lang – or even, necessarily, the way he did last month, when he was the featured soloist on the season opener for the Los Angeles Philharmonic.

Hancock's approach to the piece, he says, varies depending on two things. "One is how I make certain choices with the notes that Gershwin wrote, and the other is other liberties I take with adding things of my own to what's there."

Regarding the choices Hancock made with Gershwin's notes, Los Angeles Times reviewer Mark Swed observed that Hancock "didn't so much play the Rhapsody as investigate it … trying things out one way, then another."

Perhaps surprisingly, Hancock is a bit more conservative when it comes to adding his own notes. "If I chose to, I could, where the music stops and holds, add a completely improvised thing for a moment or two, and then have that lead to what Gershwin wrote," he says. "I haven't decided to do that when I perform in Toronto. But when I did perform with Lang Lang, because we were two pianos, it kind of made sense, because he's a classical pianist, and I come from the jazz tradition."

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Nonetheless, Hancock is keen to connect his classical background and his jazz impulses, and help bring improvisation back into the classical tradition.

"Improvisation was one of the tools of classical music," he points out. Keyboard virtuosos from Bach to Chopin to Liszt were famous improvisers, and up until the early 19th century, cadenzas – the extended solo section in classical concertos – were routinely improvised.

"But at a certain point they became repertoire," Hancock says. Specific cadenzas were written out, and that's what everyone played. "Pretty soon, because learning repertoire takes up so much time for a classical pianist, there's no time to learn to improvise.

"So one of the things I'm interested in is sparking up a new interest in classical musicians for improvising. Not necessarily improvising in a swing way with jazz – yes, if that's what they want – but also improvising in a classical way."

Hancock himself has been practising "improvising in a classical way" himself, something he says takes a lot of work. "But if it's not hard, then I'm not working hard enough," he says. "I have to make it a challenge."

Herbie Hancock performs at Massey Hall in Toronto with the Massey Hall Orchestra on Oct. 22 at 8 p.m.; and at the Jack Singer Concert Hall in Calgary with the Calgary Philharmonic Orchestra on Nov. 9.

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