Bruce Cockburn might not be a household name among guitarists, but not for any good reason. Very few players are as prolific and wide-ranging as Cockburn, whose 31 studio albums draw equally from early rock ’n’ roll and country, from free jazz and ethnic music.

Cockburn, 66, got started in the late 1950s in Ottawa, Canada, playing Elvis Presley songs on a junky old acoustic before delving into jazz. After high school, in the mid-’60s Cockburn headed to Boston, where he broadened his horizons, both musically and culturally, while studying at the Berklee College of Music.

After Berklee, Cockburn headed back to Canada, where he revisited his roots in various rock groups. By 1970, when he released a self-titled debut, Cockburn had emerged as an acoustic singer-songwriter with a surefooted fingerstyle technique.

Since then, Cockburn has evolved as both a solo artist and bandleader, and his songbook has grown to include hundreds of finely crafted songs and instrumentals. At the same time, his humanitarian work has taken him to impoverished areas and war zones all around the globe—experiences that have filtered into his music in a highly exciting way.

In 2009, Cockburn visited war-torn Afghanistan, and that trip inspired a song and an instrumental on his latest effort, Small Source of Comfort. The album is packed with plenty to offer guitar fans of all stripes—deftly fingerpicked passages in alternate tunings, improvised interplay, all kinds of fancy chords, and more.

So many burgeoning guitarists today have inexpensive but high-quality instruments, as well as instant access to lessons in all styles on the Web. How were things when you first got started, in the late 1950s?

The first guitar I had was a no-name six-string that I found in my grandmother’s closet. It had been set up as a Hawaiian guitar with this extra-high nut. I was interested in playing Elvis and other rock ’n’ roll–type stuff, so I took the guitar, painted gold stars on the top, and starting banging away. Thankfully my parents expressed their nervousness by insisting that I take lessons and learn to play guitar properly—and that if I wanted to play guitar I couldn’t get a leather jacket and grow sideburns. The good thing is that I got the guitar lessons and went on from there.

What did you learn in those early lessons?

The guitar lessons that I took broadened my horizons vastly. I started out just learning rudimentary rock and country songs by ear, but then my teacher introduced me to players like Les Paul and Chet Atkins, with their more sophisticated approaches to the instrument. These influences eventually led me to jazz.

As you gathered musical knowledge, what kind of instruments did you play?

My first serious guitar was a Kay archtop, which I traded in for a Gibson ES-345. It was the stereo model, which seemed like a strange gimmick—the top three strings were supposed to come out of one amp and the bottom three out of another. After that, I had a jazz box—a twin-pickup ES-175—for a long time.

As for acoustics, I had a no-name classical for a while but I didn’t really like it—the nylon strings didn’t offer enough resistance for the kind of fingerpicking I wanted to do. So I got a Martin OO-18 and ended up using it on my first several albums. That guitar is actually still around. At one point I gave it to my then-wife, and in turn she gave it to a friend of ours, who still has it.

When did you first get into jazz, which has obviously had a big influence on your writing and playing?

I started listening to jazz in the early 1960s and learning all about it through buying copies ofDownBeatmagazine when I was in high school. I would read about guitar players like Wes Montgomery, then go out and buy all the albums of his that I could afford. Through the drummer Chico Hamilton I got into the Hungarian-born guitarist Gábor Szab—, who brought a kind of odd Eastern European sound to jazz. Hamilton was primarily playing compositions by [saxophonist] Charles Lloyd—music that was quite fresh and captivating.

After high school you went to the Berklee College of Music. What was it like there in the 1960s?

Ottawa was a nice pace to grow up but it was very one-dimensional; I rarely, for instance, encountered black people there. In contrast, Boston was such a culturally fertile place, and the mid-’60s was a great time to be there.

What were you like as a player at that time?

Pretty crappy [laughs]. I knew more than some of my friends at Berklee because I had taken those lessons early on and been introduced to more sophisticated ways of approaching the guitar than found in rock ’n’ roll, but I didn’t really have a style of my own. I was being pulled in many different directions and was not so good at any of them.