Prettyman began her career playing locally in clubs and bars throughout San Diego County before being invited to join Jason Mraz on his national tour.
Prettyman spent winter 2004 in New York collaborating with producer Josh Deutsch.

Twentythree, Prettyman's first album, was released on August 2, 2005, when she was 23 years old.
The title pays homage to the 23 Enigma, a concept referring to the abnormally high occurrence of the number 23 in daily life as described in the book Cosmic Trigger by Robert Anton Wilson.
The album peaked at number 24 on Billboard's Top Heatseekers chart.
Prettyman's second album, Hello...x, was released in 2008 and sold 18, 187 copies in its first week, debuting at 27 on the Billboard 200.

Prettyman plays and endorses Taylor Guitars, as well as Fender & Gretsch.
A former Roxy model and avid surfer, Prettyman was interviewed by Men's Fitness in 2008 and questioned about surfing and staying active while on tour.

In June 2012, "My Oh My", the first single from Prettyman's third studio album Cedar + Gold was released.
Cedar + Gold was released on October 2, 2012, and peaked at number 47 on the Billboard 200 and 19 on US Top Digital Albums.
The music video for the album's second single, "I Was Gonna Marry You", also debuted on October 2.
Prettyman toured with The Script in October and November 2012 in support of the album. "
Say Anything" from Cedar + Gold is featured in the 2013 film Safe Haven and accompanying soundtrack of Nicholas Sparks's novel.

On October 27, 2014, Prettyman released her EP "Back to Home."
It is her first independently released album in ten years.
Prettyman began her career playing locally in clubs and bars throughout San Diego County before being invited to join Jason Mraz on his national tour. Prettyman spent winter 2004 in New York collaborating with producer Josh Deutsch.
Twentythree, Prettyman's first album, was released on August 2, 2005, when she was 23 years old. The title pays homage to the 23 Enigma, a concept referring to the abnormally high occurrence of the number 23 in daily life as described in the book Cosmic Trigger by Robert Anton Wilson. The album peaked at number 24 on Billboard's Top Heatseekers chart. Prettyman's second album, Hello...x, was released in 2008 and sold 18, 187 copies in its first week, debuting at 27 on the Billboard 200.
Prettyman plays and endorses Taylor Guitars, as well as Fender & Gretsch. A former Roxy model and avid surfer, Prettyman was interviewed by Men's Fitness in 2008 and questioned about surfing and staying active while on tour.
In June 2012, "My Oh My", the first single from Prettyman's third studio album Cedar + Gold was released. Cedar + Gold was released on October 2, 2012, and peaked at number 47 on the Billboard 200 and 19 on US Top Digital Albums. The music video for the album's second single, "I Was Gonna Marry You", also debuted on October 2. Prettyman toured with The Script in October and November 2012 in support of the album. "Say Anything" from Cedar + Gold is featured in the 2013 film Safe Haven and accompanying soundtrack of Nicholas Sparks's novel.
On October 27, 2014, Prettyman released her EP "Back to Home." It is her first independently released album in ten years.
Tristan Prettyman