Grammy Award-winning jazz vocalist Kurt Elling makes his Berkeley debut Sunday night at Freight & Salvage with special guest Marquis Hill on trumpet. Photo: Anna Webber

As one of the most celebrated jazz singers of his generation, Kurt Elling, 51, spent a long time as a solitary figure without any company in the spotlight. These days however, he’s not looking quite so lonely. When the Grammy Award-winning vocalist returns to Berkeley Sunday night at Freight & Salvage, he arrives as a trailblazer rather than an anomaly.

In a Bay Area convergence, several of Elling’s most creatively potent male peers are also performing around the region in the coming days. Fellow Grammy winner Gregory Porter, 47, presents his orchestral ballad-laden program “Nat ‘King’ Cole and Me” Saturday night at Stanford’s Memorial Auditorium. The urbane Bay Area jazz/R&B crooner Nicolas Bearde performs Saturday at Oakland’s Piedmont Piano, and on Thursday Oakland’s incandescent Kenny Washington, 61, performs Duke Ellington’s Nutcracker Suite with the Marcus Shelby Orchestra’s  at the SFJAZZ Center (with Berkeley vocalist Tiffany Austin).

While Porter got his start singing in his mother’s church in Bakersfield, Elling was deeply involved in several choirs as a child where his father was Kapellmeister at a Lutheran congregation. Music was always a passion, but before Elling started to pursue jazz he started a graduate program at the University of Chicago Divinity School. Before long however he was devoting most of his time to music, sitting in at jazz spots around Chicago and soaking up wisdom from veteran musicians.

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“I had a lot of things to figure out,” he says. “I wanted to get as much of the map of the history of thought in my consciousness as possible. But I wasn’t clear what I was going to do for a living. It seemed obvious to me it would be something in academia, or the World Council of Churches. But I discovered my talents and gifts did not lie among the professional academics. I treasure that time and still value the possibility of being a scholar, even if I’m not a professional.”

Part of what has set Elling apart is that he infuses each project with keen intelligence shaped by rigorous research. His latest release The Questions (Sony Masterworks) continues his collaboration with saxophone star Branford Marsalis, who produced the album after featuring Elling on 2016’s Upward Spiral (Okeh). For his Freight performance, Elling performs with Stu Mindeman on piano and organ, bassist Clark Sommers, guitarist John McLean, drummer Christian Euman, a graduate of the prestigious Thelonious Monk Institute, and special guest trumpeter Marquis Hill, a fellow Chicagoan who won the Thelonious Monk International Trumpet Competition in 2014 (the same year Berkeley High alum Billy Buss placed second).

While The Questions can feel a little weighty and portentous, Elling is grappling with the state of the union, and his choice of material reflects a gimlet-eyed view of our present unpleasantness. Eschewing subtly, he opens the album with a thoughtful reinvention of Dylan’s “A Hard Rain’s-a-Gonna Fall” that begins a cappella and swells into full band accompaniment. Covering a wide array of material from Peter Gabriel’s “Washing of the Water” to his beatific rendition of “Skylark,” Elling is often at his best setting lyrics to existing works like Carla Bley’s “Lawns,” Jaco Pastorius’ “Three Views of a Secret” (rechristened as “A Secret in Three Views”).

If the queries implied by the album title aren’t always obvious, what’s clear is that Elling continues to live up to the promise of his first album, 1995’s Close Your Eyes (Blue Note). He’s carried the torch of vocalese, the practice of writing lyrics to previously recorded solos, and he’s honed a more demanding discipline by soloing with impromptu lyrics, what he’s called ranting, which is like poetry slam meets riffing.

A master of collaboration, Elling been the creative catalyst behind numerous projects inspired by literature. In his hometown, Chicago, he’s worked with the renowned Steppenwolf Theater on a variety of shows, including one based on Allen Ginsberg’s poetry, and another exploring the different artistic currents of L.A., Chicago and New York.

Elling has even become a muse for other musicians. Bassist/composer John Clayton worked closely with Elling on his epic suite Red Man Black Man, a work-in-progress that premiered at the 2006 Monterey Jazz Festival, the same event that saw Elling featured in Dave Brubeck’s festival commission, Cannery Row, a work based on Steinbeck’s great novel. Pianist Fred Hersch credits Elling’s voice as a muse for his musical setting of Walt Whitman’s Leave of Grass.

“I pretty much had Kurt Elling in mind from the very beginning,” Hersch told me in a 2005 interview. “I really respect his musicianship, his diction. When you’re singing lines like ‘I celebrate myself,’ and ‘I sing myself,’ you have to own it.”

Editor’s note: This article was corrected after reader A.P. Ferrara let us know that Elling was not making his Berkeley debut, as originally stated, as the singer had played Berkeley before.

Freelancer Andrew Gilbert writes a weekly music column for Berkeleyside. Andy, who was born and raised in Los Angeles, covers a wide range of musical cultures, from Brazil and Mali to India and Ireland....