The Pretty Little Blues: Nellie McKay

Just about every corporate-funded mall-punk band makes a mighty noise about how it'll never sell out, how uncompromising its ideals will remain till the bitter end. Ditto so many blustery heavy metal eunuchs, pickup-truck-shilling macho cowboys and swaggeringly narcissistic rappers. But the most confrontational and defiantly risk-taking musician of our times might be a dainty young woman who likes to sing about cupcakes, happy flowers and walking her dog. Even as an unknown 20-year-old, Nellie McKay was precocious enough to land Beatles engineer Geoff Emerick as the producer of her debut CD (a double album!), Get Away From Me, which was released by Columbia/Sony Records in 2004. When she sang, "I should have signed with Verve instead of Sony," on the song "Clonie," it came off at first as a typically playful joke, but turned out to be a warning sign about her increasing frustrations with the label.

Amy T. Zielinski

McKay echoes the sophistication of the Gershwins without seeming to be on a retro kick.

McKay took the reins to produce her next album, Pretty Little Head, working out its intricately jazzy arrangements and duetting with such guest stars as Cyndi Lauper and k.d. lang. She further revealed a gift for crafting airy pop songs like "Pink Chandelier" and "Happy Flower" that echoed the sophistication of the Gershwins without seeming like she was on some retro kick. The deceptively cool "Columbia Is Bleeding" masked a chillingly modern animal-rights anthem, and she spat out a dazzlingly dizzying array of rapid-fire urban imagery on the hip-hop-grounded "The Big One." But the New York singer's ongoing battles with her record company escalated when Columbia execs refused to release Pretty Little Head as another double album, deciding instead to cut seven tracks (which weren't exactly filler) and shrink the remainder down into a bowdlerized single disc. At a notorious concert at the Troubadour in November 2005, she confessed her despair, sobbing uncontrollably as she urged her fans to e-mail then-Columbia CEO Will Botwin and demand the release of the unadulterated version. Her crying jag wasn't like the scene in Nashville where Ronee Blakley's character has an onstage breakdown and can't go on; instead, it felt cathartically exhilarating and genuinely emotional as McKay continued performing, directing her somewhat astonished backup band even through her tears. Not long after that show, Columbia/Sony dropped her from its roster, supposedly the result of a staff shake-up at the company and not because of McKay's pointed criticisms. She was eventually able to license the complete Pretty Little Head for release through her own label, Hungry Mouse, in 2006.

Her outspokenness and dexterous wit are what make her such a charming entertainer, whether she's name-dropping Elsa Lanchester, Michael Moore and Gabriel Byrne between (and sometimes during) songs or ranking the various late-night talk shows she's performed on ("Why does appearing on David Letterman always make me so tense?") and cheekily imitating Paul Shaffer's backing vocals. At a solo gig at the Hotel Cafe in March last year, McKay dealt with conflicting audience requests for her early songs "The Dog Song," "Sari," "I Wanna Get Married" and "Won't U Please B Nice" by combining them all into a deftly improvised medley.

Given her big mouth, it's a bit surprising that she was in a laconic mood in a phone interview late last year, declining to state what city she was in ("I'm somewhere on the East Coast") and deflecting questions about her new CD, Obligatory Villagers (on Hungry Mouse, with distribution from Vanguard), by saying she prefers that listeners come up with their own interpretations. The album title evokes a multitude of merrily conflicting images — the village idiot, Hillary Clinton's child-rearing strategies, or perhaps angry townspeople lighting torches and looking for the Frankenstein monster — while the music is buttressed by stellar visitations from alto saxist Phil Woods and Schoolhouse Rock composer/onetime Miles Davis vocalist Bob Dorough. "Mother of Pearl" starts out as a swinging little tune that appears to poke fun at politically correct feminists before neatly subverting sexist expectations. "Oversure" is a jazzy ramble, while "Identity Theft" is soaked in a sunny calypso groove and "Politan" is a romantic Spanish interlude. She's carefree and silly on the swampy blues novelty "Zombie," but McKay makes her deepest impact amid the festively tangled horns of the uplifting epic "Testify."