Her beachside town allowed for many surfing excursions, and Prettyman practiced the sport often as a teenager. She also took a liking to the music of Ani DiFranco, Joni Mitchell, and Jack Johnson, and her father's old acoustic guitar gave her the chance to learn an instrument and hone her songwriting skills. In between modeling gigs and surfing trips, she began showcasing her acoustic songs at local parties and small-sized venues. She also landed a song on the soundtrack to Chris Malloy's 2001 surf film, Shelter, which helped cement her status as a budding musician.

The buzz around Prettyman continued to grow as she toured with G. Love & Special Sauce and fellow San Diego-based folk-popper Jason Mraz. She recorded and self-released the Love EP in 2003, and considering the mainstream success of Mraz and Jack Johnson, it wasn't long before the majors came calling. Prettyman eventually signed with Virgin Records. Her debut offering of acoustic folk-pop, Twentythree, appeared in August 2005, featuring contributions from Mraz, Norah Jones' guitarist Jesse Harris, and several ace session players. Hello...x followed in 2008 and broadened Prettyman's palette, with electric instruments and slick production beefing up her songs. In 2012, Prettyman released the introspective, but still electric-sounding Cedar + Gold. ~ Andrew Leahey & Johnny Loftus