Kevin Berry calls himself Portland's "King of Old School." But he's been around long enough to remember when everything old was new.

A former KBOO host, Berry began booking classic R&B acts—from Zapp and Roger to Midnight Star to Evelyn "Champagne" King—at long-since-shuttered downtown clubs in the late 1980s, catering primarily to black audiences that were otherwise ignored by the city's entertainment infrastructure.

That's what he continues to do today, right up to this week, when he brings '80s rap icons Doug E. Fresh and Kool Moe Dee to town. We spoke to Berry about how concert promotion has changed, and exactly when the old school got old.

WW: When did you start doing concert promotion?

Kevin Berry: I think the first show was the late '80s. It was this group called Radiance, from Oakland, California. It was at the art museum. It wasn't very good. I took a loss on the show.

How has promoting shows in Portland changed in recent years?

It's different in the sense that it's more divided now. Back in the late '80s and '90s, the music was universal, as far as R&B. Young folks listened to the same stuff the older folks listened to. In the clubs, you had a mix of that, you might have people who were 21 to 55, 60 years old. Today, you've got your hip-hop that appeals to the younger crowd, and your older clientele doesn't want to mix with the younger crowd.

When did that divide happen?

It was probably '97, '98, right around in there. The transition was taking place, with hip-hop coming in more. After that, that's when it started becoming divided up.

Portland has had a problem with the police cracking down on shows that bring out black audiences. Did you have problems with the city authorities back then?

In my opinion, there's always been an issue with having large crowds of black people in downtown Portland. Back in the '80s and early '90s, that's where the main clubs were. And there always was a problem, where you do get the tension, like the powers that be didn't like to have black clubs downtown.

What was the craziest demand you've have had from an artist?

One artist, in their rider, they asked for a large box of latex condoms—Magnums. I did not supply that [laughs].

Do you feel a responsibility to continue entertaining that older black audience?

Honestly, yes. That is a part of it. In my years at KBOO, I was a volunteer all those years. For many years, I bought and paid for my own music, to stay current with the music coming out. And it's because I was trying to fill a void. I enjoy doing it, even now. It can be a headache, but I do it because I enjoy doing it, and I do know there is that need for that type of thing for black folks here.

SEE IT: Doug E. Fresh plays Tao Event Center, 631 NE Grand Ave., with Kool Moe Dee, on Thursday, March 24. 9 pm. $35 advance, $45 day of show. 21+.