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Andrew Bird leads his trio at the Green Mill in Chicago’s Uptown neighborhood on May 29, 2024.  (Chris Sweda/Chicago Tribune)
Andrew Bird leads his trio at the Green Mill in Chicago’s Uptown neighborhood on May 29, 2024. (Chris Sweda/Chicago Tribune)
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If only every concert shared more in common with the special jazz-themed performance Andrew Bird presented Wednesday at Green Mill. At the first show of a sold-out doubleheader, the veteran singer-songwriter embraced levels of intimacy, freedom, warmth and openness that are impossible to replicate even in mid-sized theaters.

For 70 minutes, Bird, bassist Alan Hampton and drummer Ted Poor operated as if they had just rolled up to a friend’s house in a van and set up in a large living room. Casual and comfortable, cozy and relaxed, displaying no concern over the video cameras filming the event. Hardly caring about a handful of false starts that helped underline the in-the-moment nature of the endeavor. With limited space to move on a compact platform and no real distances between them, they played within arm’s length of one another — close enough that they could both hear and feel the vibrations of their instruments.

Relatedly, the trio treated the iconic Uptown room as an invisible fourth member. Clear, close-up acoustics allowed notes to fully decay and transformed pregnant pauses into the equivalent of strummed chords. Fans, who gained admission by winning a ticket lottery, seemed aware of their fortune of witnessing up-close an artist who normally appears at much larger venues. They remained silent and, in a pleasant twist from contemporary mores, generally refrained from pulling out phones and watching everything through a six-inch screen.

The only drawbacks? The necessary exclusivity. As with any unique and small-scale show, let alone one headlined by a critically acclaimed and Grammy-nominated artist, few people got the opportunity to attend. A shame, given the musicianship, chemistry and earnestness on display. (Bird also appears Friday at Old Town School of Folk Music for a sold-out Chicago Humanities Festival performance and conversation.) And the relatively brief length, primarily a consequence of the night’s back-to-back schedule. However, leaving everyone wanting more never goes out of style — akin to many of the standards Bird interpreted during the concert.

On paper, the shows functioned as an album-release party for Bird’s “Sunday Morning Put-On,” a low-key tribute to midcentury small-group jazz and the Great American Songbook. Yet the occasion held deeper meaning in that it brought Bird’s storied relationship with Chicago full circle.

Despite relocating to California nearly a decade ago, Bird grew up in Lake Forest, graduated from Northwestern University and spent his younger adult years in the city. While in his 20s, he resided in an apartment-hotel building in Edgewater. There, Bird spent countless late Saturday evenings listening to “Blues Before Sunrise” on WBEZ, soaking up the wisdom of old 78RPM records spun by deejay Steve Cushing.

When that radio show ended at the tired hour of four in the morning, he went to bed before waking to the late Dick Buckley’s golden-age jazz show on the same station. Bird, who fuses a multitude of elements into his own work, credits his exposure to those programs as a massive influence on his repertoire and craft. He also cut his teeth in tiny local clubs covering some of the songs he heard on WBEZ.

Dialing back his signature quirkiness, and stripping songs down for trio arrangements, the 50-year-old vocalist conveyed that fare — standards famously covered by Frank Sinatra, Chet Baker, Miles Davis, Nat King Cole, Billie Holiday, Sarah Vaughan and other giants — with enchanting sincerity and nuanced depth. Rather than sound retro, or attempt to merely recreate the past with facsimile versions, Bird came across as classic and modern, respectful and original.

With rare exception, he bypassed the loops that inform a majority of his own material. He leaned on acoustically based rhythms, improvised directions and brilliantly adapted his violin to suit parts that traditionally called for horns. Bird accomplished comparable feats with his voice. Tender and heartfelt, his deliveries captured the hope, yearning and infatuation nestled at the center of the love-struck narratives.

Audience members listen in as the Andrew Bird Trio performs at the Green Mill in Chicago's Uptown neighborhood on May 29, 2024. (Chris Sweda/Chicago Tribune)
Audience members listen in as the Andrew Bird Trio performs at the Green Mill in Chicago’s Uptown neighborhood on May 29, 2024. (Chris Sweda/Chicago Tribune)
The Andrew Bird Trio performs at the Green Mill on May 29, 2024. (Chris Sweda/Chicago Tribune)
The Andrew Bird Trio performs at the Green Mill on May 29, 2024. (Chris Sweda/Chicago Tribune)

Wearing a sport coat and jeans, his face adorned with his familiar five o’clock shadow, Bird sang as if he had written the lyrics or lived the experiences. He frequently squinted and closed his eyes, and tilted his torso to the side, his head a bit reluctant to follow the lead of his shoulders. The spontaneous actions and animated looks underscored the seriousness of his approach and adoration for the music. Yes, he whistled, too. But that hallmark skill ceded to vocal techniques that seldom emerge in his folk, pop and rock-based material.

Crooning with an expressive sensitivity and self-examination that recalled Sinatra’s saloon songs, Bird dove head-first into the melancholic admissions of “I Fall in Love Too Easily” and pained circumstances of “I Cover the Waterfront.” His clean, beautiful violin tones mirrored the aching elegance of his controlled singing and formed twilight melodies that snaked in and out of the band’s spare architecture. Whether shaping a lush ballad or vamping on a romping blues, the trio conjured senses of wonder, possibility and delight.

All the better for dreamy escapades such as “My Ideal,” during which Poor’s soft vibraphone strikes gave Bird’s swooning fantasy an added atmospheric dimension. Affection and wishfulness similarly washed over “You’d Be So Nice to Come Home To,” reimagined by Bird and company as a lullaby with a kick. The trio opted for more delicacy on the blissful “I Didn’t Know What Time It Was,” whose delayed pace and faintly brushed drums evoked the tick-tocking mechanisms of an analog clock you implore to move faster so that time impossibly manages to speed up.

Andrew Bird performs at the Green Mill on May 29, 2024. (Chris Sweda/Chicago Tribune)
Andrew Bird performs at the Green Mill on May 29, 2024. (Chris Sweda/Chicago Tribune)

Goosed by Poor’s pliable wrists and ability to instantly shift tempos, the trio proved just as seasoned at tackling a few upbeat numbers. It streaked through an invigorating version of Lester Young’s “Gigantic Blues,” complete with freelance exchanges between percussion and stand-up bass. Bird swayed and stepped to a lively “Sweet Lorraine” and, in professing his desire for the namesake woman, extended a prevalent motif: romance, and the spectrum of highs and lows that result from that emotional state.

Slightly deviating from the planned setlist, the group sandwiched three originals — including the humorous and reflexive “Why?,” a nearly 25-year-old cut that dates back to his first band, Bowl of Fire — amid the jazz classics. Only “Armchairs,” with its tangle of complex wordplay and ebb-and-flow momentum, stuck out as an interloper. It also marked the lone instance of Bird trading the violin for a guitar. The way things were going, he didn’t need to make the substitution. And he probably knew it.

“We are so lucky we get to do this,” Bird stated, emphasizing the last word. Ain’t that the truth. Whatever it takes, well-known artists need to do “this” far more often.

Setlist for the early show at Green Mill on May 29:
“Softly, as in a Morning Sunrise” (Romberg and Hammerstein cover)
“I Fall in Love Too Easily” (Styne and Cahn cover)
“Caravan” (Duke Ellington cover)
“I Didn’t Know What Time It Was” (Rodgers and Hart cover)
“My Ideal” (Whiting, Chase and Robin cover)
“Why?”
“Sweet Lorraine” (Burwell and Parish cover)
“Gigantic Blues” (Lester Young cover)
“You’d Be So Nice to Come Home To” (Cole Porter cover)
“I’ve Grown Accustomed to Her Face” (Loewe and Lerner cover)
“Bloodless”
“Armchairs”
“I Cover the Waterfront” (Green and Heyman cover)

Bob Gendron is a freelance critic.