New England-born singer/songwriter James McKenna got his start musically, while serving in the US Navy. Late at night, he would sing while his fellow shipmates jammed on their guitars in the deep recesses of the USS Enterprise. James found he enjoyed singing so much that when he left the service, he decided to pursue a career in music.

In 1998, soon after his discharge, James took a job as a bouncer for a bar in Boston to pay for tuition at UMass Boston where he majored in music. His experiences at the bar inspired him to write one of his first and most popular songs, Seven Cigarettes. With the help of a friend, he cut a rough demo which he gave to a fellow employee for some constructive criticism. He was immediately asked by the bar owner to play a gig there. After two shows he attained a residency at another local club and eventually ditched the bouncer job for one as a paid musician. paying his way through school by playing countless shows in New England bars and clubs.

James built quite a following in Boston as he attained a BA in Music w/Focus in Voice from UMass- Boston. It wasn't long before his friends on the west coast started advising him to move to Los Angeles and give the business a real shot. Packing up his gear and trekking across the country, he started the grind all over again, getting a day job and playing the bars at night. Soon after, he fell in with fellow New England transplant and up-and-coming producer, Billy Schliefer. The two teamed up to record the EP Seven Cigarettes and formed a band in order to perform around Los Angeles.

Australian Football commentator, Dennis Cometti stumbled across James' music while perusing the online distributor, CD Baby. Dennis emailed James with words of encouragement and a wish to lend any assistance he could to further James’ career. Shortly after this email exchange, Dennis would acquire his own radio segment on Mix 94.5 in Perth, Australia. He played "Seven Cigarettes" over the air on his weekly afternoon drive segment “Dennis Does Downloads”, a make it-or-break it segment where the audience would text message their opinion to the station. The response was an astounding 96% positive!

Following the radio success, James and Dennis collaborated to adapt James' song “Jump” for use in national network AFL broadcasts. The story became a hot topic, and soon members of the Australian press were demanding to know “Who is James McKenna?”

By day, James works as a teacher of special education, helping kids diagnosed with Emotional Disturbance to learn self-control and return to a regular school environment. He draws inspiration from their struggles, channeling the themes of self-affirmation over stereotypes in songs like “I Am”.