Madeleine Peyroux

Maybe I got a lot to learn
Time can slip away
Sometimes you got to lose it all
Before you find your way…

— “Don’t Wait Too Long”

Every great musical project starts with a feeling that it’s time.

So it was, in 2004, for Madeleine Peyroux: “when I got around to making Careless Love it had been a good eight years since my first album.” Eight years—forever in the music world. Not long After Dreamland dropped in ’96, she had disappeared from the touring scene as well. Where had she been? What had she been doing, and why?

I was traveling a lot across America, rediscovering the country and re-identifying as an American. I was born here in the States but moved with my mother to live in Paris when I was young. I met family I never met before. I caught up on what was happening with the music here. It was all a culture shock for me. When I came back to New York to make that first album I was like a deer in the headlights. It was my first time in a studio, my first time back in America. Then 9/11 happened. Then George W. got re-elected. It was like the world was going crazy. After Dreamland I had signed with Sony and I was trying to make my second record. I was broke and I didn’t know what I was going to do next.

Self-reflection and spiritual sensitivity are assets to any musician in the process of starting a career, of establishing one’s musical identity and direction. They don’t, however, necessarily lock into the typical velocity of career-building. There were other things Peyroux had to handle. She underwent surgery on her vocal cords. She healed and worked with a vocal coach. As the ‘90s gave way to the first years of a new century, she continued to question the how and, significantly, the why of what she was doing. (Her choice of the Dylan Thomas quote below, from his 1946 poem “In my Craft and Sullen Art,” helps explain her creative motivation.)

“I put a lot of thought into what my career means,” Peyroux says, “what making a record and the follow-up tour represents—the kind of music I wanted to do and the amount of work that is involved.”

By 2004, Peyroux had found the answers to her questions. She signed to Rounder Records. Her distinctively updated blend of swing-era jazz, country blues, gospel, and other acoustic forms made sense on a label with a reputation for standing by singular artists dealing in, or drawing inspiration from roots Americana. It was a good fit from the start, and would lead to a run of three career-defining albums. It also led Peyroux to work with Larry Klein, a bassist whose experience covered a wide stylistic range, from rock and R&B to jazz. He had played with Bob Dylan and Herbie Hancock. By the 2000s, he had a reputation as producer of genre-straddling vocalists like Joni Mitchell, Holly Cole, and Shawn Colvin.

Rounder had me speak to a few producers they had in mind. I remember Larry stood out because he wasn’t only saying the usual things like what studio he wanted to work with. I’ll never forget this—he said he had this vision. He wanted to make a record that would sound like the dream of an album. Who says that?

Klein’s explanation, and his past credits with other singers, made the choice easier for Peyroux. Weeks of preparation ensued. The two considered a wide range of repertoire, Peyroux suggesting vintage favorites—originally recorded by the likes of Bessie Smith, Billie Holiday, Sister Rosetta Tharpe, a chanson by Josephine Baker—as well as more recent material by Bob Dylan, Leonard Cohen, and Elliot Smith. They recruited songwriter Jesse Harris to help write an original that became “Don’t Wait Too Long,” a signature tune that remains in her setlist to this day. Working with Klein also meant a major change in venue. In ’96, Peyroux had recorded in New York City, where the limited number of studios requires prior rehearsal and a pressured, hit-it-and-quit-it vibe when it came time to record. In 2004, she experienced something new.

In New York, New York, the depth of a groove is deeper and things move more quickly. In Los Angeles, I think there’s a little more lightness and a bigger range of emotion. We never rehearsed before the sessions. It was all done in the same room. We could do that because there are so many studios out there and they don’t cost as much. I was so shocked at how relaxed and slow everybody was moving when we got to the studio. It’s amazing how that affects the music, to have a studio to yourself. We had time to talk, to try out different things. The guitar vamp on “You’re Gonna Make Me Lonesome When You Go”—Dean came up with that in the studio.

Guitarist Dean Parks was one member of a studio band of delicacy and appropriate taste —also keyboardist Larry Goldings, bassist David Piltch, trumpeter Lee Thornburg, drummers Jay Bellerose and Scott Amendola—Klein assembled from a pool of session musicians. These were players adept at elevating older songs with slight, stylistic touches that avoid cliché—jazz rather than jazzy—and using musical know-how to slyly reference legacy moments: a shuffle feel on the snare, a muted trumpet, or a swing pulse on guitar. A classy touch of Western Swing courtesy of Parks’s pedal steel on “Lonesome Road.” A brief piano interlude subtly suggesting the big band standard “Stompin’ at the Savoy”—as Goldings does on “J’ai deux amours.” A haunting, legato bass line akin to the ostinato on Miles Davis’s “Flamenco Sketches”—which Piltch hints at on “I’ll Look Around”. There’s even a moment in which a vintage sound is supported by modern, cut-and-paste technique, as a looped celeste sample borrowed from a Nino Rota soundtrack recording sounds the church-bell pattern on “This is Heaven to Me.”

The album took pride in its pedigree even in title: naming itself after a W.C. Handy classic that Bessie Smith and many singers of her generation made famous, including a Dylan tune that melds seamlessly with the collective, relaxed vibe, and adds one more “careless love” in its lyric.

As the sessions progressed, with time for all to relax and be with each other, Klein allowed the musical stew to simmer until it was ready. They developed a group sound, playing off each other and the contours of the songs, enhancing Peyroux’s voice, which had matured into an instrument of disarming clarity and seemingly effortless flow.

Peyroux herself is in top, mature form on Careless Love—an apotheosis of that hushed, one-to-one affect she inherited from the likes of Billie Holiday, a stylistic bequest. By 2004, her way of conveying confessional expression was truly her own. She had developed an updated rhythmic pliability and an emotional depth that could explore the complexities lying beneath the surface of the songs. Check out how she suspends time and hovers on “I’ll Look Around,” associated with Holiday’s mid-career, pop years recording for Decca. It’s an overlooked gem on the album, Peyroux’s phrasing more in line with a Blossom Dearie ballad than Billie, way downtempo and nakedly revealing of her story-telling skill (in which Goldings points to yet another standard, “The Nearness of You.”) Peyroux transforms “Between the Bars” with a similar, open-hearted treatment, and reimagines the Hank Williams waltz, “Weary Blues,” as a prayer whispered to one’s pillow. The album’s showstopper is its opener—a cabaret-ready reading of “Dance Me to the End of Love”—which bestows Cohen’s poetic imagery with a world-weariness that can only come from experience.

Dreamland had featured a 22-year old Peyroux. She was 30 when she recorded Careless Love: “When I made my first record I wasn’t even thinking about a sense of wholeness with the music, or how to connect the songs into one overall statement.”

From initial planning to final mix, Careless Love took three months to complete. It was released on September 14, 2004. Commercially, despite Peyroux being labeled by Billboard as a jazz artist, it was a breakout bestseller matching the level of a triumphant pop music release, selling 500,000 copies within a year, and eventually earning platinum status. Overseas sales proved equally impressive; Careless Love garnered gold and platinum records throughout Europe, South America and even China. In America, its performance was certainly spurred by co-operative efforts typical of that day. Snippets of Careless Love melodies popped up on popular television shows like  Nip/Tuck, Crossing Jordan, Boston Legal, and on the soundtrack to the film Failure to Launch. “Don’t Wait Too Long” helped sell Dockers trousers in a TV ad, and Starbucks helped promote the album, strategically placing the CD by registers in their cafes coast-to-coast: musical biscotti for all those venti lattes.

Careless Love received resounding support from the critical community as well, albeit with the usual second thoughts. While praising, some reviews raised the eternal question (Is it jazz or is it not?) and many made the inevitable Billie Holiday comparison, which Peyroux did not retreat from. “I felt not only akin to but encouraged by the music Billie Holiday made as a person…I think it is the fact that she overcomes tragedy—very subtly,” she told the Los Angeles Times. Some writers could not resist the temptation to measure her against other jazz-guided singers of the moment, like Norah Jones and Diana Krall. The more astute reportage caught on that the album served notice that Peyroux had returned, more mature and self-assured. “The more I listen, the more she sounds like herself,” one reviewer stated on National Public Radio. “She makes something authentically hers out of something borrowed.”

Klein’s Careless Love studio ensemble was not able to join Peyroux on tour. A healthy number of bookings was generated by the album’s release, from late 2004 and well into 2005’s summer season. A consistent group settled into place but it took a while. “During that time, I had five different piano players come and go, two bass players, two drummers, just in order to keep musicians on the road. I was out there and the only one that was always in that picture, singing and sometimes playing guitar.” In some ways, this was familiar ground. Peyroux’s first foray into performing was as an 16-year old, busking and traveling around Europe with a rotating troupe of players. (A personal aside: in 1991 or ’92, I can’t recall exactly, while tour-managing various groups in Europe, I first encountered Peyroux singing on a Parisian street and was blown away. I had the feeling I’d be hearing her again.)

By summer of ’05, Peyroux was touring with a compatible, stable-for-the-moment lineup: Amendola, from the Careless Love sessions, plus bassist Matt Penman and keyboardist Kevin Hayes; the latter two hired on the recommendation of friends. Most gigs were being regularly recorded at the house soundboard, including one evening that took place at summer’s midpoint—July 15—at one of the older festivals on the circuit: the Vitoria-Gasteiz Jazz Festival in Spain’s Basque country. The recording of the performance, preserved by Basque Public Radio, opens with a gesture the crowd takes to heart. “Buenos noches,” Peyroux says in her best Spanish.

“You can hear how much fun we’re having, and the people sound really happy. In fact, they sound a lot happier than I remember. I think I was pretty nervous, playing in such a prestigious festival in one of these daunting, historic looking places that was so large. At the time, a venue holding 2000 was a lot for me.”

A number of things are clear from the outset on the recording. Despite Peyroux’s recollection of doubt and anxiety, the four sound exceedingly comfortable together, locking into a collective groove of the sort that sails unflappably from one melody to the next. They play to each other and to the audience; the applause markedly increases in intensity, song by song. Peyroux herself is a study in calm confidence, singing and revising how she approached each tune—holding on to a syllable here, shifting an emphasis there. “Don’t Wait Too Long” is an explicit example, and impressively, Peyroux’s rendition of “I’ll Look Around” reaches a deeper, even more personal feel than the studio version.

From pensive to sunny to outright giddy (“I Hear Music”!), Peyroux explores a satisfying mix of mood and tempi. An array of details and moments stand out in the performance’s 75 minutes, like her tasteful guitar accents on “Between the Bars” and “You’re Going To Make Me Lonesome…”—and Amendola’s mallet-play bouncing on the latter. There’s Penman’s textured feel on upright bass, guiding the pulse (his bona fides in the jazz world—as a member of the SF Jazz Collective and James Farm—are self-evident.) There’s Hayes’s skill at bringing ballads to a soft close, with just the right mood-preserving flourish on the piano. On a few upbeat numbers, with a measured touch, Hayes also weaves in the distinctive texture of the Rhodes.

The setlist derives almost exclusively from Careless Love. Peyroux brings in a few old, lively friends— Patsy Cline’s “Walkin’ After Midnight” (the kick-off on Dreamland), Dinah Washington’s “Destination Moon”, and Holiday’s “I Hear Music.” But the spotlight that evening was on her latest achievement, an album that in its sequence, track by track, comprises a complete performance. The two recordings together capture a special moment in time and offer both sides of a story that is still being written.

It is 2020. Peyroux is speaking via Zoom, in the middle of a pandemic that has silenced all live music. In this stark context, Careless Love continues to resonate, the music and the message of those songs more relevant than ever. She repositions her laptop to reveal a poster she has kept from that evening in Vitoria in 2005. It’s a reproduction of a medieval etching of a building.

“This is El Portalon—a restaurant in a building from the 1500s that’s still standing there. We ate there after the show and they had amazing food. That whole evening is still with me. This concert represents a time when there was a confluence of great things happening in my life. It felt like all the work I had put into playing music for all those years was paying off. I was working with great musicians and had a great group of songs with great arrangements.

“I can’t tell you how grateful I am that we found this recording. For me, it represents the way I understood these songs at that time, how I was making music when I made Careless Love. It’s been more than fifteen years since that record came out, and I don’t think I’ve done a single concert that didn’t include at least two or three songs from it, and sometimes more. I think I’ve sung ‘Dance Me to the End of Love’ at every show. It’s part of me now.”

2004…2005…the date stamp on any music performance can be a distracting thing. The more inspired and singular the music, the less that seems to matter. Timeless is what we call music that reaches the heart and stops the clock. Few are able to attain that, fewer with consistency. For the ones who do, it can take a while navigating one’s career path to get there, to make timeless happen. Madeleine Peyroux achieved it on her second album.