Prettyman began playing in clubs and bars throughout San Diego County before being invited to join fellow San Diegan, Jason Mraz, on his national tour. Prettyman spent winter 2004 in New York collaborating with producer Josh Deutsch who had worked with Mraz and Lenny Kravitz.
Tristan credits her brother with much influence on her thinking and the title of her debut album Twentythree pays partial homage to the 23 Enigma. A perceptual concept which refers to the abnormally high occurrence of the number 23 in daily life as described in the book Cosmic Trigger by Robert Anton Wilson, as derived from friend and fellow author William S. Burroughs.
Twentythree was released on Aug. 2, 2005,[4] shortly after Tristan turned 23 on May 23 of 2005. It peaked at 24 on Billboard's Top Heatseekers chart. The album brought comparisons with other contemporary surf rockers of the time, like Jack Johnson.[1][4]
Her second album, Hello...x, sold 18,187 in its first week and debuting at 27 on the Billboard 200.
She remains very actively involved in consistently updating her official MySpace profile and blog with stories from the road, streams of consciousness, and even a "musical" collaboration with fellow songwriters Anya Marina and Greg Laswell entitled "Lindsay Goes to Rehab," a tongue-in-cheek but friendly tribute to Lindsay Lohan, who recently entered a rehabilitation facility "to take care of [her] personal health."
Tristan plays and endorses Taylor Guitars. A former Roxy model, Tristan has also has appeared in many ads for various musical products such as Taylor Guitars.[citation needed]
In 2008, MensFitness.com interviewed Tristan on surfing and staying active while on tour. In the spring of 2009, demos of the songs, "Don't Forget to Breathe", "Like a Song", and "Better Now" appeared on her Myspace.
In June 2012, she released the first single, "My Oh My" from her new album, "Cedar + Gold".