Ray LaMontagne kicked off an evening at the First MeritBank Pavilion at Northerly Island with a twilight solo acoustic set that included “Burn” and “Jolene” from his 2004 debut album “Trouble.” The unassuming singer/songwriter’s face was obscured by a khaki hat that matched his shirt and pants until he strapped on a harmonica for “Like Rock & Roll and Radio” from the 2010 release “God Willin’ & The Creek Don’t Rise.”

LaMontagne and the Jacket boys followed “Ouroboros” with a lengthy psychedelic Hammond organ intro to “Lavender” that infused the opening track from the 2014 effort “Supernova” with the spirit of the Grateful Dead and classic Jefferson Airplane.

“It’s awfully nice to see you tonight,” LaMontagne told the near-capacity crowd. “Thanks for coming out. I’ve got one more song for you before I bring the band out.” With his hat back on, he launched into his most recognizable tune “Trouble,” singing the chorus from the depths of his soul, much to the audience’s delight.

LaMontagne’s solo sampler was well-received, suggesting that many in the crowd expected more of the same with a full band for the rest of the show. But a string of older, familiar songs perfectly suited for a Saturday night was not what the artist delivered during the remainder of the set dedicated to his latest offering “Ouroboros.”

“This album is so important to me because it wasn’t easy to get it through the system,” he said of the new album before kicking off the main part of the show. “Artists have to fight for what we do. All of us artists live and die by what we do. This is it. It’s beautiful and I believe in it. The fact that you’re all here, I can tell you how much that means to me. This short run of shows is the highlight of my career.”

LaMontagne has every reason to be proud of “Ouroboros,” a cerebral concept album co-produced with Jim James of My Morning Jacket on which he abandoned his trademark guttural, soul-drenched vocals and songs about love, loss and relationships. It’s a magnum opus that recalls Pink Floyd’s “Dark Side of the Moon,” and the remarkable effort was even more impactful when performed in full with his backing band of My Morning Jacket’s guitarist Carl Broemel, bassist Tom Blakenship, keyboardist Bo Koster, and drummer Patrick Hallahan.

The crowd’s less than enthusiastic response to “Part One – Homecoming” was the first sign that most at the concert were unfamiliar with the new album. While the bluesy lead guitar of up-tempo rocker “Part One – Hey, No Pressure” garnered a slightly better response, idle chitchat, smart phone activity and beer runs by the fourth number suggested that far too many attendees had disengaged from the band’s sonic explorations.

Despite such unfortunate distractions, dedicated aficionados were treated to high points including Broemel’s soaring lead guitar on “Part One – The Changing Man” and LaMontagne’s exemplary electricity on the instrumental “Part Two – A Murmuration of Starlings.” The lyric “you’re never gonna hear this song on the radio” from “Part Two – Wouldn’t It Make a Lovely Photograph” was also a fitting message to the surprisingly lackluster audience.

LaMontagne and the Jacket boys followed “Ouroboros” with a lengthy psychedelic Hammond organ intro to “Lavender” that infused the opening track from the 2014 effort “Supernova” with the spirit of the Grateful Dead and classic Jefferson Airplane. “Airwaves” from the same album received a different live performance upgrade, further strengthened and enhanced by Broemel’s solid pedal steel guitar, followed by a rousing version of “Drive-in Movies.”

The band’s departure from the stage, alongside fireworks from Navy Pier (shown briefly on the venue’s video screens), finally shook the remaining fans out of their stupor into a standing ovation for an encore of “She’s the One,” “Julia,” and “All the Wild Horses.” Better late than never, but LaMontagne’s entire musically ambitious and extremely well-crafted performance deserved such support and attention throughout the whole show.

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For additional information on Ray LaMontagne, visit RayLaMontagne.com.

Upcoming concert highlights at FirstMerit Bank Pavilion At Northerly Island include Josh Groban with Sarah McLachlan (Aug. 9); Carnival Of Madness featuring Shinedown (Aug. 16); Mad Decent Block Party (Aug. 21); Counting Crows and Rob Thomas (Aug. 24); Slightly Stoopid (Aug. 26); Fifth Harmony (Aug. 31); The Loop Luau featuring Sammy Hagar & The Circle (Sept. 2); Bryan Adams (Sept. 15) and Pretty Lights (Sept. 23-24). For additional details, visit LiveNation.com.