"In that, I have victory for my art and a great loss for my heart.

Prettyman spent winter 2004 in New York collaborating with producer Josh Deutsch who had also worked with Mraz.

Twentythree, Prettyman's first album, was released on August 2, 2005 when she was 23 years old.

The album peaked at number 5 on the Billboard 200 and sold over 100,000 copies in the US. It debuted at number 3 on the Billboard 200 and was an international commercial success primarily due to the hit "I'm Yours".

In 2008, Mraz released his third studio album, We Sing. The song peaked at number 6 on the Billboard Hot 100, giving him his first top ten single, and spent a then-record 76 weeks on the Hot 100.

The title pays homage to the 23 Enigma, a perceptual 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.

The music on the album was compared with that of other contemporary surf rockers of the time, such as Jack Johnson.

Prettyman plays and endorses Taylor Guitars, as well as Fender & Gretsch.

His fourth album, Love Is a Four Letter Word, peaked at number 2 on the Billboard 200, his highest-charting album to date.

Mraz has won two Grammy Awards and received two additional nominations, and has also won two Teen Choice Awards, a People's Choice Award and the Hal David Songwriters Hall of Fame Award.

Prettyman's song "Anything at All" was eventually featured on the film's soundtrack.