Chris Cagle developed an interest in music at an early age and began taking guitar lessons when he was six. But discouraged by the difficulty in playing the instrument with his small hands, Cagle quit after one year. Despite putting his instrumental interests temporarily on the shelf, the young Cagle continued to sing and eventually began playing the piano in high school. During his senior year, he received a new guitar as a Christmas present and his interest in plucking the strings returned.

The first song Cagle ever learned on the guitar was "Free Bird" by Lyrnyrd Skynyrd, a band that would become one of his biggest influences. Cagle would attend the University of Texas-Arlington, but soon he was skipping his classes to audit music courses. After spending nights playing local clubs, Cagle left school to pursue a career in music full time. He moved to Nashville, TN in 1994 and spent the better half of a decade working odd jobs while trying to make it as a musician.

With a little bit of luck, Cagle got himself a record deal with Virgin. He released his debut single "My Love Goes on and On," in 2000 and found his name climbing the country charts all the way into the top 20. His first album followed in the autumn of that year. Play it Loud, spearheaded by the single "Laredo," was a hit with country music listeners. The album featured a country feel with a twist of country-rock, the influence of artists like Skynyrd and The Eagles coming through on several tracks. Cagle re-released the record after making the move to Capitol Records. His first original album with Capitol came in the form of an eponymous effort. Anywhere But Here appeared in 2005, followed by My Life's Been a Country Song in 2008.