Toby Lightman studied violin growing up in New Jersey, but it wasn't until college that she began to seriously consider a career in music. She studied radio and television at the University of Wisconsin, learning guitar in her spare time and singing with cover bands. After school Lightman moved to New York, where a fortuitous meeting with Wyclef Jean led to him producing her demo. The tape caught the attention of producer Peter Zizzo, who helped the young songwriter develop a light, marketable mix of subtle drum programs with plenty of acoustic guitar and Lightman's own expressive vocals. A round of 2003 label showcases led to a deal with Lava/Atlantic, and by late that year the single "Devils and Angels" was making noise at Hot AC radio formats. Early 2004 found Lightman on the road, hitting radio stations and small clubs (including opening slots for Howie Day) in preparation for the March release of Little Things. A year later, Lightman released two singles, Connect Set and Real Love. In 2006, Lightman released Bird on a Wire, an album far more noticeably mature than her 2004 LP.