Released in 2000, Nickel Creek's self-titled debut album was produced by Alison Krauss and peaked in the Top 20 of the Billboard country chart; it remained on the list for more than a year. The group's second album, 2002's This Side, built upon its predecessor's success by reaching number two. Watkins' multi-instrumental skills proved to be one of the band's key assets, and her songwriting prowess developed as Nickel Creek's career progressed.

In 2004, the bandmembers formed an ad hoc group called Mutual Admiration Society with Glen Phillips of Toad the Wet Sprocket and John Paul Jones, formerly of Led Zeppelin. The supergroup cut a self-titled album and toured in support. Meanwhile, Jones encouraged Watkins to make a solo album, which she prepared for by playing solo shows at the Los Angeles club Largo. She also played on recording sessions as a fiddle player and/or harmony singer with Hank Williams, Jr., the Chieftains, Béla Fleck, Darol Anger, Switchfoot, Jonny Lang, Dan Wilson, Ben Lee, Richard Thompson, Mandy Moore, and Alex Woodard, among others.

Developing as a songwriter, she contributed to five songs on the Nickel Creek album Why Should the Fire Die? The group went on indefinite hiatus after the disc's release, and Watkins signed to Nonesuch Records as a solo artist before contacting Jones about producing her debut album. Sara Watkins was released on April 7, 2009. The Blake Mills-produced Sun Midnight Sun followed in 2012, and featured guest spots from Fiona Apple, Benmont Tench, and Jackson Browne, among others.

A flurry of activity followed in the next few years. Nickel Creek reunited for A Dotted Line in 2014 and the next year brought The Watkins Family Hour, the first studio album by the Los Angeles-based revue led by Sara and her brother and Nickel Creek bandmate Sean Watkins. In the summer of 2016, Sara released her third solo album, Young in All the Wrong Ways. ~ William Ruhlmann