Every Wednesday night this month, the Chicago-based punk poet Ike Reilly will hold court at Icehouse to celebrate the release of his new album, Crooked Love.

The artist-in-residence concept has become increasingly common at Twin Cities venues this year, particularly in the colder and slower winter months. But for Ike, it’s an approach to playing shows that he’s embraced since his major label debut in 2001; anyone who was lucky enough to be at his explosive run of shows at the Turf Club that summer is probably still talking about it today.

“Whenever I’ve done these residencies, something cool has happened, or magical,” Ike says, sitting in the afternoon sun at Icehouse last Wednesday, just a few hours before taking the stage for a solo performance to kick off the month of shows. “Like tonight, I’m playing alone, but I don’t know what I’m doing the next shows. I’m going to play some songs tonight that I haven’t ever played. Old songs, and new songs.”

Reilly has plenty of material to choose from for the residency. He’s been performing for over 25 years and steadily releasing music for the last two decades, beginning with 2001’s Salesmen and Racists and leading up to his eighth full-length album, Crooked Love, which is out May 18. At last week's show, he set up each new song with a backstory about its lyrics and message, debuted a couple of politically charged, unreleased tunes, and dug deep into his catalog to unearth fan favorites like "Put a Little Love in It (According to John)," "Whatever Happened to the Girl in Me?" and "The Boat Song (We're Getting Loaded)."

After all those Thanksgiving Eve shows spent igniting the First Avenue Mainroom with his ferocious live band, the Ike Reilly Assassination, it was a treat to hear Reilly present the older songs in a new light — and to actually be able to hear the vivid, detailed, and sometimes disturbing human stories at the center of his work. Even in his more serious moments, however, Reilly can't help but put a wry spin on life's heavier truths. "Here's an uplifting song about a friend of mine who lit himself on fire," he said with a crooked grin before "Put a Little Love in It," the audience hanging on his every word.

In conversation Reilly is equally disarming. He answers nearly every question with a self-deprecating joke, speaking softly and bluntly, eyes sparkling mischievously. He seems to enjoy twisting his stories around and turning them inside out, as if searching for the beauty and tragedy and humor of every moment.

When asked where he finds his characters, he just smiles. "I’ve been around a lot, you know. I’ve done a lot of shit. I know a lot of people; I travel a lot, had a lot of jobs," he says. "And I don’t have an iron-clad mind, but I remember people, you know. Who they are and what they’re about. And then I steal their souls and stories. I act like I like them. And then I suck everything I can out of them."

The new album, Crooked Love, is full of these characters: a worn-out husband searching for some peace and quiet amid the paint cans and vice grips in the garage ("She Haunts My Hideouts"); a couple who are at odds with one another but still want to party ("Don't Turn Your Back on Friday Night"); an immigrant waiting at the baggage claim for his wife and realizing in a panic that she may have been stopped at customs due to the travel ban ("Bolt Cutter"). As with his solo performance at Icehouse, the album is presented with the lyrics front and center; although the album features playing from many familiar collaborators in Reilly's universe, the album has a stripped-down, intimate, and warm feel. Reilly sounds more present in the studio than ever before, like he's singing to a handful of people rather than a sold-out, wasted crowd.

"This one has a vibe to it," he says. "If I were to throw all my other records away — and it’s not just because it’s new — this is the one I’d want people to hear. It sounds fresh but it sounds old, too. It’s definitely analog. It was recorded with a lot of tube sh*t and tape and old mics." He pauses and laughs to himself. "Hell, if I bought a mic when I was young, it’d be old now."

Although the album isn't explicitly political — especially when compared to some of the unreleased songs, like "Because the Angels," that he debuted last week — Reilly acknowledges that his music has always been written in the context of the times. With the political climate so heavy in recent years, he says the need for unwinding and sharing these story-songs feels more urgent than ever before.

"These characters are all searching for intimacy and affection in dire times," he says. "I mean, our times — it’s not dire. I’m going to stand in front of people and they’re going to drink and I’m going to sing songs tonight, you know what I mean? It’s not like pure oppression, but there’s a lot of people struggling. And hopefully when we’re celebrating, we can take a minute or two to think about it and try to do something to help it."

And celebrate he will, with a 60-date tour and residencies in Chicago, New York, and Minneapolis. Despite the fact that he has always been based in Libertyville, Illinois, Reilly plays enough shows in town and has such a devoted fanbase here that he's practically a local artist — just what is it about Ike Reilly and Minneapolis?

"I always like it here, you know," he says. "It’s a great city. I have connections to other places, but I have some good friends here. I would say, to the Minneapolis crowd, if you’ve never seen the IRA or me, this would be a great place to do it because it’s so intimate, and you’ll get to hear — and you know, you can leave easily if you don’t like it. In fact, I’ll give you your money back."

Ike Reilly plays Icehouse tonight with Mary Bue; returns on Wednesday, May 16 with Hannah Von Der Hoff; and finishes his residency on Wednesday, May 23 with Natalie Lovejoy.