Starr's shows have been described as "marrying pop smarts and Americana grit with a voice of remarkable power and clarity".

Since that initial record, Starr has released over a dozen EPs and LPs while landing numerous placements on shows and movies like Grey's Anatomy, Pretty Little Liars, Nashville, Hart of Dixie, Switched at Birth, Rookie Blue, Army Wives, and Brothers & Sisters, as well as commercial placements that include Pandora, Virgin Mobile, McDonald's, and Fisher Price.

[5] Starr was signed to Geffen Records, which released her first major-label album, featuring Bob Rupe of Cracker and The Silos, Eighteen Over Me, in 1997.

In those years, the songs that she had begun working on at Geffen evolved and changed significantly before reaching the final versions that appear on the album.

The second EP, 2000's Somethin' To Hold You Over, was self-released for fans and included several original tracks, as well as a reworking of "Molly" from Eighteen and "5 Minutes," which would appear in a different form on her next album.

In Los Angeles, she gained inspiration for two albums, Songs from Take-Off To Landing and Airstreams and Satellites, which was released in October 2004.

Starr re-recorded "Superhero" for Airstreams, which also includes a hidden track, "Inside Out", in which she makes her first definitive reference to being a lesbian.

[10] In 2005, Starr appeared with other artists in a series of performances at L.A.'s Room 5 as the North La Brea All Star Conquistadors.

[11] The group, consisting of Starr, Gabriel Mann, Jay Nash, and Adrianne, toured the eastern United States in spring 2007.

[13] Starr's song "Superhero" has appeared on several compilations, including Live at World Cafe and CMJ magazine's sampler.

Starr's "Beautiful in Los Angeles" was the featured song on the season one finale of MTV's original program The Hills.