NOT THAT anybody was counting -- okay, a lot of people were counting -- but it was seven years between albums for Esthero. In pop years, as in cat years, that's about half a lifetime, a perilous gap for someone whose 1998 debut, "Breath From Another," introduced the hypnotic singer and down-tempo diva whose sound one critic dubbed "Bjork meets Billie Holiday."
Esthero's voice is in fine form on "Wikked Lil' Grrrls," which, like its predecessor, is a genre-hopping delight, from the Bjorkish "We R in Need of a Musical Revolution" and chamber-pop "Everyday Is a Holiday (With You)" to the swing vocal stylings of the title track, the sexually charged R&B of "If Tha Mood," a jazz-tinted "Melancholy Melody" and other tracks hinting at trip-hop, hip-hop and beyond.
"My taste is so vast it ends up like a premixed iPod shuffle," notes Esthero from Portland, Maine, where she's opening for John Legend. (She'll be doing a solo date at the Black Cat on Sunday.) "Some people appreciate that, but I've gotten as much flak for it, as if it's disorganized.
"It's the double-edged sword, and it's intentional," she adds, calling the album "snapshots of my life over the last seven years. The only continuity in it is that it has no continuity, just like me. I'm constantly changing. I like so many genres of music, but I believe that there's only two kinds -- there's soulful and soulless."
Soulful seems to be what people tapped into, not just the quarter-million who bought "Breath From Another," but a host of musicians who connected with the 27-year-old Toronto-based singer (born Jen-Bea Englishman in Stratford, Ontario). They include Sean Lennon (who co-wrote "Everyday Is a Holiday"), OutKast's Andre 3000 (on the new album's funkalicious "Junglebook") and ex-Goodie Mob-ster Cee-Lo Green, who guests on the plaintive breakup song "Gone" and first worked with Esthero on the Goodie Mob remix of "Country Livin' (The World I Know)" that appeared on the soundtrack to the 1998 film "Slam."
"I was the only non-hip-hop and the only white artist on the soundtrack, and they wanted an urban remix for radio," Esthero says. "I was a Goodie Mob fan, but I would have never thought they would have said yes. And it was amazing -- after the record came out, I started getting calls from American hip-hop folks and getting love from them, which was a really, really cool."
In fact, even as her second album was in limbo, Esthero was collaborating with such artists as Mos Def, Saul Williams, Rascalz, DJ Krush and Lisa "Left Eye" Lopes (just before her death in 2002). And she'd pop up on occasional club hits, including Ian Pooley's "Balmes (A Better Life)," Black Eyed Peas' "Weekends" and her own "O.G. Bitch," which topped Billboard's Hot Dance Music/Club Play chart in 2001. There was an EP last year (three of its six tracks reappear on "Wikked Lil' Grrrls") and contributions to several film soundtracks as well as a track ("Nearly Civilized") for the Sony PlayStation2 game 007: Nightfire.
But there were also contractual problems. The label that had signed Esthero at age 18, Work Group, was absorbed into Epic, and the singer was quietly "released" from her contract. In 1999, she signed with Reprise but found herself addressing both writer's block and corporate hurdles. It took a year from the time Esthero finished writing and recording "Wikked Lil' Grrrls" to Reprise starting to remix it, and it wasn't mastered until six months after that. The title track, she says, is partly a tribute to the '90s Riot Grrrl rock movement ("that was high school for me"), as well as "a love letter to the strong, amazing women in my life and the idea that so many girls that are comfortable with their bodies or sexuality or that are mini-feminists are usually referred to when they're children as wicked, naughty little girls. So let's just wave that flag!"
The most noticeable testament to the album's delays is "We R in Need of a Musical Revolution," which attacks monotonous, oversaturated radio programming and moral decay in pop music (targeting R. Kelly in particular). "I'm so sick and tired / Of the [expletive] on the radio and MTV / They only play the same thing / No matter where I go, I see Ashanti in the video / I want something more."
Problem was that Ashanti was pretty much over by the time the song was released. "When I wrote it, the Ashanti comment was relevant," Esthero laughs. "By the time we mixed it, I was secretly hoping she would resurface with something so that my statement would be relevant!" Ashanti did -- as a pitchwoman for Herbal Essences shampoo. "Secretly I was going, 'Yes, now my song makes sense!' "
Her own road back to relevance was a mixture of "being around other creative people" and finding the path in her own time. "The route I took was to simply stop and live," Esthero explains. "You have to remember, I was a little kid when I made my first record -- 16, 17 when I wrote it, 18 when I got signed, 19 when it came out, and those were like my journal babblings from grade 9!
"All of a sudden, I had a lot of convenience at my fingertips, and if I was bummed I could fly away to my apartment in Los Angeles or whatever," she adds. "I grew up without a lot of money and suddenly had, not a ton of money, but more than I'd ever had. And life got really . . . convenient. I always talk about the grand irony that you don't have to be miserable to make good music, but the irony for me was that as soon as I went broke and lost everything and was miserable and got heartbroken, that's when art came."
"For me, a big part of [the delay] was removing myself from the life I had created, or stumbled into, and just be and garner some experience."
On the other hand, music was about the only thing Esthero had ever aspired to. "I don't have any recollection of ever wanting to do anything else," she insists. "I have memories of being 3 and during the holidays grabbing a guitar and strumming nothing on it, putting on a concert for my family -- I am a rock star! I remember their mouths agape and them laughing at me. It was probably really horrible."
Or not, since Esthero's father had been a musician in the '60s under the name Teak Wood ("when I was a little girl I didn't understand the reference -- that it was a real wood -- just thought it was a cool name"), and she and her brother Jason (known as J. Englishman) moved to Toronto when she was 16 to pursue parallel career dreams. Esthero was soon discovered singing Bjork and Annie Lennox songs in local coffeehouses and signed to EMI Publishing, which advanced her money for demos. She then hooked up with transplanted American musician-programmer Martin "Doc" McKinney to produce "Breath From Another."
The name Esthero, she has explained, was inspired by a character named Esther spotted in a late-night movie on television: Her last line is, "If I am to be the hero, then I cannot fly from darkness." Esthero was initially the duo's moniker, as well as the stage name the singer decided to adopt. The partnership with McKinney ended a few years after Esthero had become the latest down-tempo, trip-hop diva, following in the footsteps of Bjork and Beth Gibbons of Portishead, though the singer expressed frustration with the label. "I never understood it because if Bjork is trip-hop and Massive Attack is trip-hop and Tricky is trip-hop, then which one's the real trip-hop? Because they all sound totally different to me."
What Esthero does acknowledge is that it was "hip-hop kids, the urban community in Canada, that gave me the most love before anyone, and it was unexpected because I grew up listening to a lot of British shoe-gazers like My Bloody Valentine. When my first record came out it was like, if [MBV singer-guitarist] Kevin Shields thinks it's okay, then my job is done. I thought it would be the kids who were into those groups, because it was sort of a natural break-off from Spiritualized, early Verve records and Jesus and Mary Chain into Portishead and Massive Attack -- that was the next generation."
But although "Breath From Another" earned a lot of critical attention, Esthero points out that "as far as the sales aspect of it, it didn't do as well as everyone hoped. For me, I was just a kid from a small town, so the fact that 100 people had my record and I had opportunities to travel with other musicians I loved, to me it was a success already. I was still young and green, and I didn't understand the business. I didn't understand: How could 250,000 records be a failure?"
"But investing a couple of million and not getting it back made it a failure in everybody else's eyes. That was a learning experience for me."
Still, as much as label problems fed the long delay between albums, Esthero concedes, "a lot of it had to do with me. But being where I am now -- and I'm going to sound like a hippie -- the journey makes sense, and it doesn't seem that long anymore. It seems totally natural that I put one foot in front of the other and took the steps I took to get where I am now and to finish the piece of art that I made. It's what it needed, and I think I learned enough and made so many mistakes that it's not going to take that long again. It's really about what the universe allows. Sometimes you're supposed to be there and you're supposed to be working and doing things and it just doesn't come, and that's what I told the label. If it doesn't come when I want it, why should it come when you want it to?"
"The universe doesn't put you anywhere that you don't need to be. Hopefully I won't have to be wherever I'm supposed to be next time for seven years."
ESTHERO -- Appearing Sunday at the Black Cat with W. Ellington Felton.