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Angel Olsen keeps it real and heartfelt in her concert at Thalia Hall, with opener Kara Jackson

Call it kismet that Angel Olsen began the first of her sold-out three-night stand at Thalia Hall only four days after Merriam-Webster named “authentic” the word of the year. Friday at the Pilsen venue, the singer-songwriter epitomized the essence of the term, which the dictionary defines as “not false or imitation” and “true to one’s own personality, spirit or character,” among other meanings.

Unscripted and unfiltered, Olsen couldn’t have better fit those descriptions. She used the performance to explore the boundaries, roles and feelings associated with romance — and frequently, its messy aftermath. Unbeholden to the visuals and lighting synchronized to songs at most larger-profile shows, Olsen went old-school and winged it. The 36-year-old St. Louis native played what she and her versatile support band wanted at that moment. Relishing the idea of surprise, she solicited and granted requests, rendering the setlists taped to the floor an afterthought.

The good-natured demeanor carried over to her sense of humor and spontaneous banter. Olsen freely conversed with the crowd, shared details about her life and divulged a big secret. Namely, that she got engaged to collaborator (and auxiliary instrumentalist) Maxim Ludwig. He was onstage as Olsen confirmed a blurted-out suspicion about her status.

Ah, the hopes and optimism tied to forthcoming marriage. No wonder the vocalist beamed throughout the 95-minute concert. At several points, Olsen fought back laughter in the middle of songs. On “Right Now” she neglected a verse due to becoming overcome with glee. Later, she cheerfully warned a fan that they were going to cause her to lose focus.

Certainly, the avoidable mistakes and lack of polish — extending to Olsen’s tendencies to go off on tangents as she tuned her guitar or interrupted a lyric with an impromptu observation — fell short of the predictability and perfectionism associated with conventional pop standards. Good on her. Olsen’s onstage traits, and fact she didn’t employ vocal-correction software or backing tracks, signaled a genuineness and accessibility often absent in the mainstream. She further compensated for any lingering nerves or awkwardness with an irresistible draw: a pliable, gorgeous, widescreen voice that penetrated with devastating emotional intensity.

Olsen has been a constant in music circles since emerging from the Chicago scene nearly 15 years ago. That coming-of-age period witnessed Olsen toil as a part-time waitress, flirt with massage-therapy school and record a lo-fi EP (“Strange Cacti”) before landing a gig in 2010 as a background touring vocalist for eccentric folk artist Bonnie “Prince” Billy. A debut LP and record deal soon followed.

Angel Olsen performs at Thalia Hall in Chicago on Friday.

Ditto critical praise, festival slots and a relentless work ethic. Olsen, who currently resides in Asheville, North Carolina, released five albums and two EPs in the past decade. In 2021, she came out as queer and dealt with the deaths of her adoptive parents in quick succession. (She has since clarified that she identifies as a pansexual.) Those transformational episodes fueled the country-leaning “Big Time” (2022), her most recent effort. For Olsen, channeling pain, grief and love into shared experiences is old hat.

Olsen combined all three conditions in multiple songs, including “Sweet Dreams,” a dirge that witnessed the singer blend sorrow and devotion in aching fashion. Burrowing into tight crevasses and probing unexpected places, her falsetto nearly transformed into a yodel as she emphasized the word “alone” and phrase “on your own” in separate stanzas. Laden with reverb — too much so, at the start of the show — Olsen’s singing faded into the ether, the final syllables echoing like a haunting memory that never dies.

Loss, and the thorny matters that surround how such situations arise, informed much of the material. Underpinned by groaning organ accents and clip-clop rhythms, “This Is How It Works” conveyed claustrophobic desperation. Similarly melancholic, the hymnal strains of “Endgame” chronicled the dissolution of a relationship built on false pretense. Framed by three keyboards that approximated symphonic strings, Olsen’s weary, head-on-the-floor vocals simultaneously evoked defeat and disgust.

Yet the vocalist regularly arose above the fray, shying not away from sadness but rather refusing to wallow in self-pity or act as a victim. Searching, defiant, assertive: Olsen issued challenges and posed tough questions even when her deliveries turned inward by way of fragile inflections and whispered softness (“Ghost On”). And for all the uncertainty wrought by the infatuation circling the biting “Give It Up,” Olsen wrestled back control of her identity and purpose on a majority of the excursions into heartbreak and disappointment.

Shaking her arms, she brought her voice to a resistive shiver on the demanding “Go Home,” projecting with a volume that stood up to the building swell of crashing cymbals and chiming guitars. Olsen gained strength as the epic “Woman” unfolded, citing personal sacrifices en route to meeting feedback head-on with siren-caliber vocals that escalated the drama without obscuring the honesty. She dialed down the anger and opted for a sweeter approach for the insistent “Shut Up Kiss Me.” For Olsen, it was a rare occasion where physical affection trumped the intimacy associated with the heart, soul and mind.

Kara Jackson opens for Angel Olsen at Thalia Hall in Chicago on Friday.

Opener Kara Jackson reveled in a different kind of closeness. The Oak Park native and former National Youth Poet Laureate — whose “Why Does the Earth Give Us People to Love?” LP ranks as one of the year’s most acclaimed debuts — performed a bracing 30-minute solo set that demanded quiet. The audience, which included some of her friends, dutifully complied.

Primarily singing in a dry, husky low register, Jackson disarmed with sparse arrangements and naked, raw tones. Amid the hushed environment, she made no attempt to conceal any sound. The scrape and squeak of acoustic guitar strings during chord changes; the gentle thump of her fingers landing on the fretboard and left hand rubbing against the neck; the purposeful inhale and exhale of breath from her lungs. All audible, all part of minimalist tapestries that evoked the woozy sensations of awakening from a dream state on a late Sunday morning.

Though Jackson’s folksy songs offered limited variation, her vivid images and metaphors threatened to burn holes in bystanders’ imaginations. Flashing a droll wit, she struck a self-assured presence that mirrored the maturity of her storytelling. In addition to a winning cover of Karen Dalton’s “Right, Wrong or Ready,” Jackson impressed with originals that addressed themes of self-worth, anxiety and expectation with a plain-spoken directness and tender vulnerability that bordered on distressing.

Half-jokingly deemed as mostly “pessimistic” by the singer, the fare poked and prodded, with the only splendor reserved for a few high-end vocal flights. Let other artists embrace ornate trimmings; Jackson needn’t fanciness for her clearest revelation — one that appeared to arrive via reflection and healing following a forgettable interlude.

“I am pretty top-notch,” she repeated, convincing herself of a truth at the end of a bluesy number that cursed sycophants and parasites. “I’m useful.”

Bob Gendron is a freelance critic.

Setlist from Thalia Hall Dec. 1:

“Dream Thing”

“Spring”

“Shut Up Kiss Me”

“Give It Up”

“Sweet Dreams”

“Right Now”

“Ghost On”

“Go Home”

“This Is How It Works”

“Special”

“Sister”

“Endgame”

“Sans”

“Some Things Cosmic”

“Un(expletive)theworld”

Encore

“Woman”


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