Cook, 47, has released eight studio albums, a trio of live DVDs, been the subject of a couple of high-profile PBS television specials and earned a Juno award along the way.
He's travelled widely and has absorbed the diverse cultures and music of the places he's visited, managing to incorporate much of what he heard organically into what has become his own worldly musical sound.
Interested in music from an early age, Cook studied classical guitar for a time, but frustrated by the limited repertoire, basically walked away from the instrument.
But a casual childhood conversation with a friend in Toronto led him to revitalize his love of playing and led to a vibrant career.
"To give you an idea of how little I was playing (guitar) at the time, he was my closest friend and he didn't realize I played the guitar," he said. "I had kind of put it in the closet and forgot about it.
"He said 'I want to learn the guitar,' and I said, well, I can teach you how to play. He said 'Really?' You can play the guitar?'
So I pulled the guitar out and dusted it off and started playing again. We formed a band and seeing how much fun he was having made me realize I was missing out on the fun part of music."
Cook will stop in Kelowna on Tuesday on an extensive tour of B.C. and Alberta, which actually kicked off in Vernon on Monday.
Cook's early life was, like his music, a multi-cultural experience in many ways.
Born in Paris to photographer and filmmaker John Cook and his wife, television director and producer Heather, Jesse Cook spent his early years moving between Paris, southern France and Barcelona.
The creative environment natural to his family - famed Canadian artist and photographer Arnaud Maggs is an uncle - he became fascinated by his parents recording of legendary gypsy flamenco guitarist Manitas de Plata.
"My mother told me when I was three I would sit in front of the speakers and just kind of bop away to the music," he said. "I had this little toy guitar my family picked up in Spain and I would play that and sing Guantanamera, or whatever."
When his parents separated, Cook moved with mother and sister to Canada. Recognizing his musical aptitude, his mother enrolled him in classical lessons at Eli Kassner Guitar Academy.
"I didn't really like it much," said Cook of the repertoire he was learning. "It didn't seem (very broad).
"We would go to see a concert; we would go to see John Williams play or Julian Bream, and they would be playing the same repertoire as me, just because everybody was playing the same pieces. I thought, 'If they're doing what I'm doing already, what's the point?'
"So at the age of 13, I dropped classical.
"I wanted to be a Harlem Globetrotter â€¦ that was my life ambition."
Fortunately, Cook had that conversation with his friend and instead re-dedicated himself to the guitar. He also broadened his musical studies and went on to explore jazz and work on composition at Toronto's York University and then at Berklee College in Boston.
While Cook certainly respects the individual forms that flavour what he plays, his approach is more open.
"What I'm creating is a hybrid," he said. "I realize on the Internet I'm often referred to as a flamenco guitarist or a flamenco fusion guitarist and there are certainly elements of flamenco in what I'm doing. Personally, I would never refer to myself as a flamenco guitarist.
"For one thing, I know what flamenco is â€¦ and as much as I love and respect the tradition, I don't feel it's my torch to carry."
His last album was also a departure of sorts for the Toronto-based musician. Taking inspiration from British singer Adele and others, like jazz trumpeter Miles Davis, Cook pared down his sound on 2012's Blue Guitar Sessions, and explored the more understated and blues-influenced music he was writing at the time.
While his new approach has made for a different sound for Cook, he can still take an audience on a musical journey that crosses cultures and boundaries, no matter what others may call it.
"I tend to refer to myself as just a guitarist and let people make up their own minds when they hear the music."
Who: Guitarist Jesse Cook in concert
Where: Kelowna Community Theatre, 1375 Water St.
When: Tuesday, Mar. 4 at 8 p.m.
Tickets: $42.50 plus fees and taxes. Available online at selectyourtickets.com or by calling 250-762-5050