After graduating, Pilley moved to New York City to pursue a music career, surviving the rat race to land some helpful day jobs. She played keyboards on the show Spotlight Cafe with Denis Leary and in the house band of the MTV show Turn It Up. She sold a couple of her songs to actress/singer Jennifer Love Hewitt. She was music director for the off-Broadway musical Tony and Tina’s Wedding. This last job led her to a gig as film composer for the low-budget romantic comedy The Rules for Men.

All the while, Pilley was rehearsing and playing shows with her band, Ila’s Dress, which initially included drummer Frank Vilardi, later a member of Jewel’s backing band. The current Ila’s Dress lineup includes bassist Jay Bianchi, guitarist WHO?, and drummer WHO?. After several showcase appearances in New York, Ila’s Dress entered negotiations with various major labels.

In the midst of the discussions, however, Billboard published an article announcing the signing of Ila’s Dress. The other labels under consideration withdrew their offers. Now forced to deal with just one label, the band was between a rock and a hard place. Pilley began to see the music industry’s “ignorance and bad manners” as her creative control dissolved before her eyes. She started to wonder if a major label was really where her music belonged, and eventually, she walked away from the deal.

Pilley turned this frustrating situation into something productive, using the experience as songwriting fodder; the first Ila’s Dress album was entitled Ignorance and Bad Manners. Yet Pilley’s trials weren’t over. She tried a couple of radical image changes that she now regrets: first vamping like Alannah Myles and other pop sexpots; then adopting a French accent and the distant attitude of a lounge chanteuse. But her sense of self was too strong to stay buried beneath any facade.

This powerful individuality is stamped all over Pilley’s music. Her classical training lends her songwriting a natural structure and melody, yet she doesn’t mince any words. In fact, she’s had to learn to edit herself a bit. For instance, after her major-label experience, she jokes, “I wrote songs with names like ‘You’re a Big Wienie with a Little Dick.’”

Pilley’s Southern roots show up in the tangy twang of numbers like “I Love You (Whoever You Are)” which appeared on the soundtrack of the Kevin Smith-produced indie film Big Helium Dog. A musical combo of alt-rock, pop, and modern country propels her rich, emotive voice through the angst of “Not Necessarily Those Things.” Pilley can even write convincingly from another point of view, as in the raw, scathing “Heal Me,” a Fiona Apple-esque catalog of missed opportunities that bears little resemblance to Pilley’s own happy childhood. When she turns to her own disappointments, the result is more funny than spiteful. The catchy kiss-off “I Like to Think of You Dead,” targets all those people you love to hate. Before you know it, you’re singing along, enjoying a cathartic dose of humor, and marveling at Pilley’s unquenchable spirit.