Esthero (New York, NY – August 17, 2006)

Esthero is tiny and striking in person. The curves of her distinct facial features are betrayed by the one-dimensionality of photographs—there’s a constant movement about her, even when she’s sitting quietly on a stool, singing a slow song. With her orange hair piled into a short hive, and with her slightly exaggerated lips and teeth, she looked a lot like Lady Kier’s little sister during her one-night stand at the Maritime Hotel’s Hiro Ballroom in New York City. If she were more famous, there’s no doubt she’d be popular with female impersonators, though it’s hard to imagine a drag queen putting on a more entertaining, over-the-top performance.

Shortly after her prompt arrival on the stage of the 600-person capacity venue (accompanied by her little white dog, who followed her and then dozed off), Esthero promised the show would be “like VH1 Storytellers, but way fucking drunker.” She’s a woman of her word, and after several fan-sponsored shots of Jägermeister, the Canadian singer’s set spiraled into what felt like drunken—albeit still well-sung—karaoke. Though I’m pretty sure she didn’t wind up peeing in the parking lot, as she claims to have done in the past, it was still an unfortunate turn of events for a woman who, sober, is a much more engaging performer and a better singer than you might expect. She’s quite incredible, in fact.

Esthero opened the show, billed as “An Intimate Evening with Esthero – Acoustic Style!,” with “If Tha Mood,” a racy track from her 2005 album Wikked Lil Grrrls, and then invited requests from the audience. Two hours later, she’d covered a wealth of material from the new record—“Gone” was the biggest crowd pleaser, especially among the black females in the audience—as well as her debut, and managed to squeeze in covers of the Lemonheads’s “My Drug Buddy,” Concrete Blonde’s “Joey” (the song that scored her a management deal years earlier), the Roots’s “You Got Me,” and an impromptu medley of Björk’s “Army of Me” and “Possibly Maybe” (she does a wicked impersonation, accent and all). And her original material, which runs the gamut from trip-hop to R&B, worked surprisingly well in the acoustic format.

Esthero spent half the night telling stories, as promised, and the more inebriated she became the longer the stories got (and the digs at her record label became more and more frequent), climaxing with a hilarious, extended tale about the late Lisa “Left Eye” Lopes and Krispy Kreme donuts. She brought her similarly-dressed friend, the talented Shae Fiol, on stage to sing her song “A Woman’s Presence” while she took a break, smoking a cigarette and contributing occasional harmonies. She wandered off-stage a few times, further interrupting the momentum of the show, but all the while managing to keep her composure. “Can you do this when you’re drunk?” Esthero quipped, a roar of applause translating into an unqualified “No!”

Esthero ended the show (with “We R in Need of a Musical Revolution”—another promise kept from earlier in the night), not because she was too drunk, but because she was forced to. Her idea of “revolution,” however, is questionable. All of the artists she named during the fist-pumping performance of the song (some of whom were in the audience)—John Legend, Bilal, Olivia—are more respectable than the artists she condemns in the lyrics, but they’re far from revolutionary. Esthero is more radical than any of them, at least in spirit. Much to the dismay of the bar’s management, she added a second encore with a cover of Olivia Newton-John’s “Magic,” an anthem, she said, for anyone over 28, with a vagina (even “a new vagina”), or gay, inviting them all on stage with her—to the further dismay of the management. “Arrest me,” she said. Spoken like a true revolutionary.