On her 2021 album Psychology of Jazz, Debby Yeager sings with conviction and confidence. That’s not the same as hubris: she’s seen too much, and felt too much, to ever think she has all the answers. But the lessons she’s learned inform her phrasing and her dynamics. They steer her voice, this soft/strong instrument, toward intriguing shores. That’s not quite the singer you hear in this onstage recording from nearly 25 years ago, yet there’s a strong connection nonetheless. Live 1999 documents the maiden voyage of Yeager 2.0. It’s the first puff of wind that propelled Debby Yeager on the journey of the last quarter- century.

Don’t get me wrong: Yeager’s performance on this date, a tossed- together benefit evening in Newport Beach, California, doesn’t require excuses. While she says today that “It’s not my best,” there’s still a lot to recommend – in the downy texture of her voice, the light sway of her swing, the unassuming, even intimate invitation to her listeners. Her interpretations don’t beat you over the head; they massage the heart. And in light of the circumstances, they reveal a survivor’s grit at work and at play.

Yeager had built a career and a resume as a vocalist in the 1980s and 90s. But in the several years prior to this set, she had essentially dropped off the scene, as she focused on healing herself in the aftermath of trauma. “I couldn’t even get on stage,” she says. “I was licking my wounds, hiding out, in a way, trying to figure out what to do next.” She became a counselor for abused children, even though, as she recalls, “I missed the music terribly. But there was too much going on.”

By 1999, though, Yeager felt ready to dip her toe back into what she loved best. In April of that year, she put together a small tour in Southern California to raise awareness for National Child Abuse Prevention Month, thus bridging her work with troubled kids. Her pianist for these shows was the often astonishing, wholly underrecognized Milcho Leviev, a Bulgarian émigré who had first gained attention in the U.S. as a member of Don Ellis’ boundary- busting big band in the 70s. And as April came to a close, Yeager hastily assembled the rest of this band for a benefit south of Long Beach, CA (home of KLON radio, which hosted the event). Leviev contacted Pat Senatore, a mainstay Los Angeles bassist; Yeager rounded out the quintet with her friends Kevin Tullius on drums and Jerry Pinter on tenor and flute.

Since she had just gotten back onto stages, and had never worked with her bassist, you’ll understand if the lady sounds a bit tentative in places; looking back at her history, I think she sounds remarkably assured. She chose the program wisely: a couple tried-and-true standards; two Brazilian tunes, reawakening her early infatuation with bossa nova; another – “The Shadow of Your Smile, also set to a bossa nova beat – on which she gently soars; an impromptu version of “All Blues,” surprisingly (and brilliantly) suffused, on the spot, with lyric bits of Stephen Sondheim’s lesser-known “I Remember.” And perhaps

Yeager’s favorite memory from this night: a moody Leviev composition, with the counterintuitive title “Happy Stuff,” on which Yeager sings no words at all: “Milcho gave me that tune a long time before this performance so I could put lyrics to it. I played it again and again and then finally I thought, ‘This is such a cool, haunting melody; I don’t want to do anything that might mess it up. It would have been overkill. So I just sang as an instrument, without words.” The pianist shines here and throughout the disc, but especially on “I’ll Remember April” and then, in an entirely different vein, on the contemplative Tullius composition “Tribute.” And don’t miss his solo on “At Last,” which culminates in a series of increasingly florid fusillades – prompting the admiring jibe, “Hey Milcho; you getting paid by the note?” apparently from the evening’s emcee. (Yeager recalls that during an earlier break, Leviev had drunk a fair amount of coffee, which may well have turbocharged that solo.

Yeager has fond memories of Leviev; indeed, his presence helped prompt her decision to release this long-lost set. And that was even before she learned of his 2019 death. “The weird thing is that the tapes were just sitting and collecting dust for 20 years,” Yeager says now. “But something kept nagging at me. I’m kind of intuitive; it’s almost like my third eye can’t shut. Every time I walked by my music room and saw the box with these tapes, I felt like it was calling to me. So finally I pulled out the project and tried to get hold of Micho, but without any luck. And then I went online and found out he had passed just two weeks earlier. It was almost like he was vibing me, influencing me to release ‘Happy Stuff’ after all these years.”

Listening now, it’s hard to square these tracks with Yeager’s self-characterization of this period. “I had been in a nosedive,” she recounts. But she also admits that as the evening dwindled and the crowd thinned, the band continued to jell; the last three tunes brook little complaint, even when stacked against her more accomplished recent work. Having quietly re-entered the jazz world in 1999, she slowly rebuilt her confidence and her career, culminating in the three recordings she has released since 2017. Now she has new stuff in the works, music that reflects her evolution as a mature, thoughtful, and effortlessly musical artist. But when you listen to the singer she is today, remember that her song starts here. - NEIL TESSER