Born in Oceanside, California in 1981, Thile grew up in Idyllwild in a musical family and first started playing mandolin around age four. It was while attending a weekly bluegrass show at a local pizza restaurant that he met the brother-and-sister duo of fiddle player Sara Watkins and guitarist Sean Watkins. Together, they formed Nickel Creek and recorded two albums before releasing their official debut, 2001's Nickel Creek. Produced by Alison Krauss, the album hit the Billboard 200 and quickly elevated the group's status as rising stars of the progressive bluegrass sound. With Nickel Creek, Thile released a handful of highly regarded albums, including 2002's This Side, which won the Grammy Award for Best Contemporary Folk Album, 2005's Why Should the Fire Die?, and 2014's A Dotted Line.
On his own, Thile debuted with 1994's Leading Off... and 1997's Stealing Second. Largely traditional bluegrass productions, the albums were particularly impressive considering that he was only 13 years old and 16 years old, respectively, when they were released. They also found him backed by such bluegrass luminaries as Jerry Douglas, Stuart Duncan, Alison Brown, and others. That said, the albums were primarily showcases for his growing abilities as a gifted teenage performer.