I wrote this song in 1999. I came up with the main themes and was playing around with them, when I realized I needed to get my good friend Caleb Phillips a gift for a 'bachelor blessing' party we were giving him. I was torn between keeping working on the song and going to a store for a gift, when I realized the song was the gift. Caleb and I had played together as a guitar duo, although he wasn't as serious as I was about music. He had decided to pursue computer programming instead, so we had disbanded the duo a few months prior.
In 'Caleb's Song' I tried to write a guitar 'duo' that could be played on one guitar. On the recording, the first section of the song repeats with an overdubbed part on top of it. I can use a 'loop pedal' to accomplish this live, although most of the time I just combine the ideas in a single part. I finished the song that day and played it for him that evening at his blessing party. It proved to be a better gift than anything I could have picked up at a store, and I've played it at hundreds of weddings since then.