Playboy didn’t know what it got itself into in 1999 when the magazine included Richard Thompson in its blanket request for current musicians to compile a list of the 10 best songs of the millennium. Although he knew the magazine was really seeking titles from the recording era of the last 80 years at best, Thompson called their bluff and came up with a far larger inventory that started in 1000 AD and spanned 13th century rounds, medieval ballads, 16th century dance music and Gilbert & Sullivan right up to Prince and Britney Spears.

Playboy didn’t print Thompson’s list, but no matter. The singer-guitarist-songwriter – long a maverick whose multitudinous output in the folk-rock oeuvre rivals any of his more famous contemporaries – instead turned it into another fascinating side project when the Getty Museum asked him to “do something different” in a concert there. That humble beginning spawned a couple of tours with the show, a 2003 album, a forthcoming DVD, and – lucky for us – a night at the Lobero on May 12 as an add-on to the Sings Like Hell series.

One could hardly think of a more appropriate musician to take on such a Herculian task. Thompson’s breadth has strained genres since his early days as a teenage member of the seminal British folk-rock group Fairport Convention, reaching an electric zenith in addressing relationships with his final album with ex-wife, Linda, the searing “Shoot Out the Lights,” and evincing a scholarly approach to music with nearly every recording and live concert since. He’s amazingly nimble on the guitar, equally able to finger-pick his acoustic with quiet beauty or shred on an electric solo that leaves you searching for the non-existing back-up musicians (he’ll have two cohorts on the current campaign: vocalist and pianist Judith Owen with percussionist and vocalist Debra Dobkin). And his dry British humor and cheeky wit bridges any of the gaps, as evidenced by a recent telephone interview from his Los Angeles home, where Thompson talked about the project and his current status.

Q. There wasn’t any radio or Billboard Top 100 back in the 14th century. How did you determine what was a “popular” song?

A. Um, guessing mostly. Actually, “popular” is misleading. We don’t really know. The only way you can tell is what was written down, or compiled into collections, which just gives you a clue. So I had to do a lot of research, passing through troubadours, early dance music, ballads in English language from 1400s, work songs, classical music. Twentieth century music has a much wider range of styles of course. Otherwise, it’s pure guesswork in the days before there were charts. The point of the show for us is to play music we like – that’s the second layer of popularity. Truly popular music, frankly, isn’t very interesting.

Which leads one to wonder about the inclusion of “Oops I Did It Again.”

That’s the rare example of a popular song that has other virtues. If you overlook that it’s Britney (Spears), it is a good song, well-structured, with tongue-in-cheek lyrics. We close the show with it because coincidentally it has a quite a medieval structure to it, so we perform it twice, first in her current version and then 16th century style.

Speaking of popularity, you’ve had a running self-deprecating joke for years about your own popularity.

It’s not so much true anymore. The music I play isn’t mainstream, but I do have a good following of people. My concerts are full, and sometimes I sell records into the hundreds of thousands, so it’s not that bad. Then again, the whole idea is of “1,000 Years of Popular Song” is preposterous, pretentious and ambitious, but the music is serious. We just do them as well as we can. There’s some irony in the playing.

How did you decide on which rock songs to include?

The criteria is we have to like them and they must be fun to perform. And we have to be able to perform them with this stripped down instrumentation. We’re simply not capable of doing some things. I picked the Beatles song (“It Won’t Be Long”) because it has three strong vocal parts. The Who song, “Legal Matter,” I can get a fairly full sound with just one guitar. We could have done a tongue-in-cheek version of a more bombastic song, that might have worked too.

On your solo shows, you seem to decide what to play on the spot, which you obviously can’t do on this concert. Is that frustrating for you?

Well, I always have a set list as a security blanket, and then drift away from that and try to respond to what the audience wants. With this show it’s more evolution than revolution; it slowly changes every night. It might be the same song but we’re doing different things, improvising in new ways. We’re still getting into the groove of it in a two-week tour, just the segues between songs is always challenging.

Speaking of challenges, I was stunned to watch the documentary on the DVD of “Grizzly Man” to see how you literally composed the music for the film on the spot. How did you do it?

I don’t know really. You have to concentrate very hard. The whole time there was the film crew in the studio and the documentary crew filming, and those big distractions force you to shut your mind of everything else but the music. It’s a challenge to write three minutes and ten seconds of music spontaneously and finish in the right place, and have the shape of the emotion of the picture. But we had a really high success rate.

What do you think you’ve learned from both of these projects?

Every outside project you do is inspiring and can teach you things that enrich you. “Grizzly” was confidence building; actually, to be able to have success in improvising that score under pressure helped me to think I can do it again, and in different ways. With the “1,000 Years,” in the research you do find musical ideas that are appealing and useful; I’ve applied them to my own music in new songs. On “Old Kit Bag” the song “One Door Opens”’s themes are like 1500s dance music themes. I know the ideas came from researching.

In examining what made a good song for the last 1,000 years, have you given any thought to your own catalogue, wondered what will stand the test of time?

No, I really don’t do that. I don’t know and I don’t care. You can’t be thinking about that when you’re making music. The music is now. The important thing is the next song, the next performances. It takes enough energy just trying to do a good job. If you start thinking about your impact on the world – “Aren’t I great!” – you just get distracted. I’m not overly fond of anything I’ve done really. I know the work I do has virtues, but I can see the flaws in everything.

Even “Shoot out the Lights?” Some call that a perfect album.

Not from where I’m sitting. From my perspective, there are a huge number of problems with that album.

I’ve got to ask you, why do you live in La La Land, the place people go to stop creating. How does it work for you?

LA is bland and a little bit sleazy. You can import your own culture in a sense. You can be British here. I don’t get distracted from my roots. If I lived in New Orleans, a place that has a strong indigenous culture, I’m sure I’d be influenced in that music. But I’m not going to start writing Jan & Dean songs because I live in LA; it doesn’t impinge on me. Then there’s the colonial view – it’s like England with better weather.

Your style and technique are so unusual. Have you ever given thought to teaching class in songwriting, guitar technique, at UCLA or wherever?

Not really, no. I could do it, I suppose. But I don’t have to. Many people who teach do it because they can’t make a living as a poet or a writer and need to supplement their income. I love to teach kids sports. But I don’t really understand what my music is, and that’s the real problem. I can’t really analyze it to the point where I can describe it. I do a lot of things that aren’t mainstream or orthodox; I play the guitar in ways I wouldn’t recommend. So I can’t imagine why teaching would work. But if my career continues to plummet, and I become unpopular, I’ll definitely resort to teaching, take it all back and I’ll find a way to do it. And I’ll be fabulous.