LAST YEAR, A FOUR-DISC collection of Richard Thompson's music was released. Walking on a Wire (1968-2009) commences with Thompson's first recordings with legendary English folk-rock band Fairport Convention, moves through the records he made with wife Linda Thompson in the '70s and early '80s, and concludes with a generous helping of selections from his solo albums in the years since. The 71-song set purports to have at least one song from every album Thompson has ever released, although his discography is so vast and sprawling that such a claim is difficult to refute.

It barely scratches the surface. Thompson is, quite simply, a titan in the history of recorded music, even if he's never achieved household-name status. His most frequently heard recordings are likely the session guitar work he did on Nick Drake's first two albums, and his most influential recordings could be the five wonderful albums with Fairport Convention, while his most critically lauded work might be the pair of albums he recorded with former wife Linda Thompson that bookended their marriage, 1974's I Want to See the Bright Lights Tonight and 1982's Shoot out the Lights. For over 40 years, Richard Thompson has been writing, recording, and performing—and for his latest batch of songs, he's doing something different.

"First of all, I was trying to save money because going to studios is expensive," Thompson says. "Especially if you have a band—and I was thinking, is there a cheaper way to record? And I thought, actually, live could be cheaper. People say that they prefer what I do live as opposed to what I do on the record. They prefer live versions of songs. So I thought, why not short-circuit this process? Let's record the songs live and see how they like that."

Thompson's two Portland dates are part of a West Coast mini-tour in which his band performs the new material—for an album to be released later this year, tentatively titled Alive, Alive-O—followed by a set of older songs. It's the Time Fades Away trick, and it's one perfectly suited to Thompson; via his website he's released a series of "official bootlegs" in recent years, live recordings which are equal or superior to his studio albums.

"Recording is a difficult process if only because you're going into a studio and you're almost recreating the excitement of performing onstage," Thompson explains. "It's sort of an artificial idea, in a sense—of playing music to yourself rather than to an audience. And I think some people can do that very well; they're able to recreate the magic. Other people make records that, to me, sound antiseptic; they sound a bit lifeless because the music is labored over in the recording process."

Thompson's music thrives in the live setting, not because he's a flashy showman, but because he's indelibly tied to the troubadour tradition of passing along songs orally. The brand of British folk that he and Fairport Convention spearheaded in the late '60s was somewhat symptomatic of the fashion of the era, but Thompson has incorporated other elements into his music—rockabilly, music hall, Renaissance madrigals, to name just a handful—that ensure his songs are never quite in step with current trends. He's both a traditionalist and a completely idiosyncratic iconoclast, and while he's a somewhat retiring and bashful individual, being onstage allows him to showcase the fact that he is one of the world's best guitarists, as well as a hell of a songwriter.

It's not a role Thompson was always comfortable with. "In the '70s I thought that the music I was making lost focus," he says. "And I started to do other things: I ran an antique shop for a while and I went exploring. I wasn't particularly excited and I couldn't quite figure out what I was doing in music. Then punk came along and I thought, well this is great, because now everything is reenergized and it's possible to see a way forwards. So thank you, Sex Pistols!" he laughs. (It should be mentioned that none of Thompson's records sound remotely like the Sex Pistols.)

"I think since then I just have a better idea of who I am as a musician and what I should be doing as a musician," Thompson continues. "I believe that every musician is different and has a gift, but musicians don't always know what their strongest suit is, what they're best at. These days I have a better idea of who I am and what I'm doing and what direction I should be taking musically."