The Illinois musician fills his eighth album, 'Crooked Love,' with typically sharp character sketches

In some ways, Ike Reilly has always been as much a character actor as a musician.

For more than two decades, Reilly, a lifelong resident of Libertyville, Illinois, has penned songs in which he has embodied an eclectic cast, his frequently downtrodden narrators hobbling along amid struggles with everything from addiction to heartbreak. The trend continues on his most recent full length, Crooked Love, from 2018, on which the singer, songwriter and guitarist explores a variety of relationships, including an immigrant couple torn apart by President Trump’s travel ban (“Boltcutter Again”), a widower attempting to dull his pained memories with gin, among other substances (“She Haunts My Hideouts”), and a violent offender hoping to find one last night of freedom in his lover’s grasp (“Missile Site”).

“My favorite songwriters were the same way, whether it was [Bob] Dylan as the character in ‘Tangled Up in Blue’ … or even going back further to Roger Miller talking about failing his wife in ‘Dang Me,’” said Reilly, who opens for Cracker at the Athenaeum Theatre on Friday, Nov. 29. “I think of songs as films and short stories. I’m always amazed when people say, ‘I can’t believe you said that in a song!’ … I mean, you make it up. You’re presenting stories and ideas and provoking people to feel good or bad or indifferent or challenged. I just want whatever is being said to sound truthful. Whether I’m singing about waiting for my daddy to die or the joy of being a father, it just has to sound honest.”

For Reilly, these disparate characters can emerge from anywhere, adapted from films, TV shows and books, and born of stories from friends or random overheard barroom conversations, their development further influenced by everything from the melody, key and speed of the song to “the level of emotion — anger, joy, whatever — that you choose to put into it.”

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While it’s tempting to describe Reilly’s characters as existing on the fringes, the musician makes a compelling case that the oppressed and their hate-filled oppressors, both of whom feature prominently in his discography, “are actually smack dab in the fucking middle now.”

“For a long time, I’ve been drawn to people who have dealt with addiction, and now more than ever we know that addictions aren’t exclusive to people on the fringes,” Reilly said. “I’ve always been interested in human struggle and triumph, whether it’s as simple as the struggle to find fulfillment or a struggle with addiction or the struggle to find love. I don’t know if I’ve ever gotten to the triumph part, but I’ve still got a few more albums left in me.”

This includes an in-progress full-length that Reilly hopes to complete sometime in January, one likely to include a handful of more straightforward, folk-leaning songs — a style and approach the idiosyncratic musician has typically avoided in the past because, as he explained, the simplicity of the form bored him. “But these songs stand on their own with the melodies and stories, and to try to infuse some bullshit production trick on them feels unnecessary,” he said. “Not that I decorated songs [on past records] because they were weak, but maybe they were less linear and more esoteric, and those types of songs are more conducive to peculiar production.”

No matter the form the album eventually takes, Reilly said he’s still driven by the same forces that motivated him to first pick up a guitar decades back.

“I’ve done it since day one as a cathartic, life-saving thing that helped me battle depression and whatever else,” he said. “I don’t know where I heard or read this, but it said that when you’re in a project, whether it’s painting a bedroom or building a deck or splitting the atom, dopamine is created, and I realize that truth, because I definitely have less depression when I’m working on a song, where I’m almost buzzing, and I feel physically different.

“I still live in the same town I grew up in, and often people will come up to me and say, ‘Hey, can you talk to my son?’ And they’ll tell me he’s a guitar player or he wants to start a band or go to the Berklee College of Music, and they’ll ask, ‘What would you tell him?’ And I say, ‘Don’t fucking do it.’ There’s only one reason to do this, and that’s because you can’t do anything else. … Those are the kinds of people I want to deal with, and those are the artists that I’m most interested in.”