Portland and the Flaming Lips go back a long way.

When the band first played here, its deranged acid punk was many years away from being safe for mainstream consumption, and the city wasn't much safer. As both entities have grown—with the Lips improbably evolving into America's cuddliest crew of psychedelic pranksters, and Portland into, well, you know—the two have remained friendly, with the band returning frequently for shows and other special occasions.

Touring in support of their 14th studio album, Oczy Mlody, the Lips are bringing their confetti-, glitter- and blood-strewn live spectacle to Roseland Theater, a venue much smaller than what they have played in recent years. So we asked leader Wayne Coyne about some of the crew's other notable visits to town.

Feb. 23, 1998: The Flaming Lips play their first Portland show at Satyricon.

WW: What was your perception of Portland back in the '80s, coming from Oklahoma City?

Wayne Coyne: It felt like the bastard daughter of San Francisco. Where Satyricon was located, I think it was right across the street from the homeless shelter. The very first time we walked into the Satyricon—we would always show up slightly early to do soundchecks and stuff, probably earlier than clubs back then even wanted—and I remember we walked into the dressing room, and someone was literally shooting up some drugs into their arm.

There was one time where there was a homeless guy out front, and he pulled a knife on the guy who was cleaning up the front of Satyricon, spraying down the sidewalk from the piss and beer or whatever. I remember sitting in our van, listening to the whole thing happening, and being terrified. I remember the guy said, "You're not going to stab me, because if you do, I'll spray you with this water." It wasn't cold, but it was a chilly enough day where you wouldn't want to be homeless and then sprayed with water. And the guy was like, 'Oh, you're right,' and the whole thing fell apart. So we walked in and did our soundcheck. So for a while, that would've been the view of it. It's got its own trip. It's not Seattle, it's not San Francisco. For us, anyway, it felt like something in between.

Do you have much of a memory of what audiences here were like and how they took to the band at the time?

In the beginning, we were definitely still playing to the druggy punk rock scene. But once Seattle took off, we didn't seem that heavy after that. We are kind of noisy, but we are kind of friendly, and we are kind of experimental, but we love to do songs. I don't think all that was sorted out just yet. By the early '90s, we were starting to get more of that audience coming because they liked our vibe or something. It wasn't just another confrontational, weirdo group. I'm sure in the beginning, people didn't even know where we were from, they didn't think about it very much. But I think the early '90s, by the time we were playing the Lollapaloozas in the early '90s, I think  Portland was warming up to us. Some of the venues there, I forget the one where you sort of play in the corner, upstairs—

Crystal Ballroom?

Yeah! For us, these would still be big shows. You're playing to maybe 1,000 people. That would be a big show for us. We would play in, like, maybe in New York or Chicago, you'd play to maybe 1,000 people back then, and Portland could be one of those, mostly just because it's got a thriving, active bunch of people. I don't think it's because of us, I think they could probably go to almost any show and there'd be lots of interested and interesting people in the audience. Little by little, I think we just became attached to Portland. Our tour manager and sound guy lives there now, and we would be recruiting people from the local scene to start to become our people helping us on the road. I think him starting to live there changed that for us as well, because people love him as well, and he's a great, creative, cool guy. I think that probably led to us being able to organize one of our great, insane videos we did there, for "Watching the Planets," the great naked bicycle ride we did.

Sept. 29, 2009: Wayne Coyne films the NSFW video for "Watching the Planets" at Mount Tabor.

So your tour manager is the one who set that up?

Well, it was a collective effort. I'd heard about the Naked Bike Ride probably through a story on NPR or something like that, and I asked him about it. He'd started to ask people if they'd like to do something like that in a Flaming Lips video. And I think in the beginning we thought, "Let's see if we can get 30 or 40 people to at least sign off on it." When you make these videos and Warner Brothers is involved, everyone has to sign off on it. And as it rolled along, he was saying, "I think we could easily get 100 people it seems like," and then a week later it was like, "I think we can get 200 people." By the time we did it, he seemed to think, "Wayne, if you want to get 500 people to do this thing, I think they'd all do it and would be glad they were part of your video." It utterly floored us how much people were embracing it. That was such a cool, cooperative moment. In the beginning, we thought, "We'll try to do this thing and see how crazy it is." And everyone who participated in it made it a thousand times better and crazier than we ever thought.

We were starting to do it up in a little segment of Mount Tabor, and the cops are being patient with us, but little by little they're like, "You can't do that here." It's starting to get dark, and word is starting to get out that there's naked people running around. And Gus Van Sant, someone in the crew knows him, and he literally says, "You can go out to my place and do whatever the fuck you want." No money, no prearrangement. Within a couple hours, we organized a bus that would take us all out there. Those are the kind of things you could never organize, you couldn't know any of that is going to happen. You just start doing it. It ends up being one of the most insane videos we've ever done—people literally running around naked, all day and into the night.

It really did change my attitude about doing big videos like that. It was better because we wanted so many people involved, and the more who got involved, the better it got. It looked better, the vibe of everybody there showed up in the footage. It wasn't something we had to construct and say, "Look insane! Run around naked!" They were doing it anyway.

I was at the shoot and remember you auditioning people to climb naked out of this big ball you were calling "the fur vag."

I felt embarrassed afterward because the one woman we had, she had these light-colored nipples, which I thought looked amazing in person. But on the video, it looked like we were trying to cover them up. I remember saying, "Y'know, your breasts just aren't working for this," and I quickly moved to somebody whose breasts looked different—not better or worse, but worked better for my video. I wasn't very tactful about it. And I regret that.

Sept. 19, 2011: Wayne Coyne comes to Jackpot Records to release the extremely limited Strobo Trip Light & Audio Phase Illusions Toy, which comes with a six-hour Flaming Lips song.

Why did Jackpot Records get the honor of releasing your six-hour song?

I'm not sure. I know that between 2010 and the end of 2011, we weren't doing a contract with Warner Brothers. We knew we were gonna redo our contract Warner Brothers, and they and us agreed we'd do a lot of weird stuff in this year to sort out how we would move forward. As we put out these things, we would try to find people that would jump on it with us. I can't remember what was all involved with that, because we would be doing two or three at a time. I'm sure it was someone connected to us who was going to help us distribute it. And that little thing is an absolutely limited thing. I mean, I don't even have one myself now. And that was part of what was cool about it. We didn't want to make it forever, and we didn't want it to be become a normal thing. We wanted to make just enough of them so the freaks out there would feel like we're doing something for them, and we wanted to do something that would push what we were used to.

Aug. 3, 2014: The Flaming Lips play Tom McCall Waterfront Park as part of Major League Soccer's All-Star Weekend.

How'd the show at Waterfront Park come together?

We're the first people on the list if there's a way we can do a free concert. That's one of the hardest things to pull off, because a lot of times, things that are free are not funded very well, either. Occasionally, you run into the right combination of people who are willing to do, not a mainstream-type concert but a Flaming Lips-type concert and still put a lot of money into it, and it becomes this great moment where normal people around the city are going to go there and the Flaming Lips freaks are going to be there. We're always wanting that, especially when it's free. We do shows all the time that cost $60 or $70 and that's just the way it is. You have to be able to make money to do things or whatever. But probably 20 shows a year or so, we'll run into people who can do a really great free show. Usually, it's some really badass, cool rich people. I've been lucky to know a lot of insanely rich people who are absolutely the most giving, the most creative people ever, and they do cool, cool shit with their money and their energy and their time. And we don't talk about it, because I don't care if people know how these things are done, but it's awesome. That's part of the circle of minds we want to be in with. 

This was during a period when you were receiving a lot of criticism for cultural appropriation, and there was a small number of Native Americans there protesting. Were you aware of that? And looking back, what are your feelings on that backlash?

I definitely regret that it offended some people. That part of it, you can't say you're right or you're wrong. If it offended you, and you feel like I'm responsible, I'm sorry for that. I think we were part of a lot of things that happened that year, where people wanted to be offended in public. You do a lot of stuff and sometimes it rubs people the wrong way, and sometimes that takes on a life of its own and it stands for something else than what really happened. But if you feel like you have something you want to say, you can absolutely say it at a Flaming Lips show. I remember being in the space bubble, and there were protesters right there in the picture—some people laughing at it, some people being upset, and some people saying, "This is a Flaming Lips show, of course, you can do whatever you want." I would oftentimes be like, "I don't think we're the enemy you think we are, but if you think we are right now, that's OK. I allow that."

SEE IT: The Flaming Lips play Roseland Theater, 8 NW 6th Ave., with Klangstof, on Friday, May 12. 9 pm. Sold out. All ages.