[1][2] James spent his early music career playing at New York City open mics before he signed to Capitol Records in 2005.

[7] After the death of a friend's mother, James sang "Candle in the Wind" at her funeral with a local music teacher he knew, Kevin Kandel, accompanying him on piano.

[9] After graduating high school James went on to attend college at the University of North Carolina, beginning with a major in Voice before switching to Communications.

[1][7] With the Clef Hangers he would sing solo covers of "I Can't Make You Love Me", "Father Figure", and "Die Without You," songs that were later released on compilation CDs from the group.

[12] While living in Los Angeles,[13] he played at a club called The Crooked Bar (located underneath the Coconut Teaszer), while working on songs and performing.

[10] In 2005 James would record another demo, this time professionally produced by Tony Bruno in Woodstock, New York[19] at the Millbrook Sound Studio.

The demo caught the interest of major labels and James did a showcase at The Living Room in New York City for various record companies.

He recorded material from the Capitol album with Los Angeles-based producer Mikal Blue,[16][22] turning it into James's self-released EP, The Ballroom Break-In, in 2007.

[23] The title of the EP was based on his early days in New York City, when he broke into venues to practice playing and writing songs on a piano.

[24][25] Music from his EP was also used in television shows, including "The Sun Will Rise" which appeared on the ABC drama Private Practice in 2007.

As his EP's exposure grew, including a feature on Perez Hilton,[27] James again gained the interest of major record labels.

[29] James initially toured regionally to support the album, headlining his own shows and also opening for artists such as Corinne Bailey Rae, John Legend, Susan Tedeschi, The Fray, and Robert Cray.

James moved from New York City to Los Angeles, where he is currently based, after having spent much time there in the past few years.

The Vespa-sponsored "green tour" with Jason Reeves and Amber Rubarth saw them traveling the California Coast on Vespa scooters while focusing on environmental friendliness.

[34] The album's single was "The Fall" and again a music video was made, this time featuring Melissa Ordway as the female lead.

He described it as "a 12 song album, traditionally recorded live with my touring band, and inspired by the style of my idols – James Taylor, Paul Simon, Bob Dylan, and others."