At this point in his career, Open Mike Eagle (born Michael W. Eagle II in Chicago) regularly books festivals like Pickathon, and is currently touring the US with his buddies WHY? He’s a well-known rapper, but still under-the-radar enough that he has to accept some awkward bookings, like a recent stint at a film festival.

“Imagine performing for a 1,000-seat theater that’s completely empty,” Eagle says over the phone from his home in Los Angeles. “By the time you’re three or four songs in, the place is filled. Some people are super into it, some can’t be bothered. I did it, like, three times and every time there was this feeling that I could only call ‘the awkward raw.’ So much of my career has put me in those positions that don’t make for a necessarily enjoyable experience.”

Such is the curse of someone who once dared to self-describe his genre as “art rap.” Eagle says he feels more comfortable in the company of middle-aged stand-up comics than his hip-hop peers. His appeal is immediate. Since emerging from the Project Blowed collective in the late ’90s, he’s maintained a calm, measured flow that allows his verbal roundelays (“So I take five, Dave Brubeck/I make jazz jokes so I’m flat broke/Mad at Lost and that black smoke”) and razor-wire wit to slice you to ribbons before you realize what hit you.

Eagle cuts deepest when he’s commenting on the struggles and triumphs of Black Americans. It’s a thread that winds through all of his work, but feels like it’s wound even tighter around his most recent album, 2016’s Hella Personal Film Festival. Every goofy bar is countered with something more serious, as on the incisive “Smiling (Quirky Race Doc),” which burns with frustration and awe at the state of modern race relations: “Today I saw a lady say hi to a stranger/Then avoid my eyes like I’m a white person strangler/Walking past voters in democratic blocks that hit the windows and the automatic locks.”

But like most hip-hop artists traveling to the Northwest, Eagle will likely be dropping those rhymes to a primarily white audience. Does that change the way he performs or even what songs he plays?

“There’s a couple of lines in some songs that I might skip if I feel the wrong kind of white vibe,” he says. “It doesn’t happen very often, but when it does it’s pronounced. You get that feeling that maybe the guys in the back of the room aren’t that hip to you as the guys in the front. Those times I’m not as straight-up provocative along racial lines as I can be.”

At the moment, Eagle’s developing some TV projects he won’t reveal any details about, but that will likely be a cogent response to the current political climate. And he’s going to continue making music, but with a more focused eye on a creative, if not commercial, breakthrough.

“I’ve been trying to inch my way towards a process that is a little more fluid,” Eagle says, “and developing the arrangements and sound quality more. I want to make big boy records. I make records in my house and I love them, but want to make big boy records now.”