James was born in Lewiston, Maine to Lawrence and Katherine (McIlroy) Flynn. He is the fourth of five sons. He grew up in Monmouth, Maine and Lewiston Maine, where he was a member of a high school choral group.

 Flynn's philosophy on songwriting is interesting. He believes he is a "small frog in a small pond. Flynn finds enjoyment in simply knowing people are enjoying his music. Flynn adopts some of his songs to video, that he posts to a YouTube account. On YouTube, Flynn's songs have found moderate success, being played 100,000 times, as of December 2008. Flynn's songs are played regularly by various artists on independent country stations.

Flynn enjoys writing story songs, and songs that pull the listener in. The song he personally believes is his best is titled "MegaFlight." MegaFlight discuses how it would be if it where possible to visit lost relatives and friends in heaven. The song tells the story of a man who was married to a woman that died in childbirth. In the song, the unnamed man goes to an airport to inquire about purchasing a jet ticket to heaven for him and his young child. He has also written songs in other styles, such as "The Ballard of L.L. Bean".

Awards and Achievements

Flynn is noted for his song writing ability, and has been rewarded for his achievements by many organizations. In the 2005 DECMA awards, he won first place in the "Best Folk Songwriter" category for a song called "The Ballard of L.L. Bean", and took second place in two other songwriting categories.In 2006 he wrote a song titled, "The Opening Act," a song that later became the title track to child performer Brian Wardwell's first album. At the DECMA "Legends Show", Jim was awarded a Founders Award for his efforts in behalf of the Maine country music community.