He is a member of the contemporary folk band Nickel Creek, the duo Fiction Family and the supergroup Works Progress Administration.

The band has released six albums and a CD composed of their hits (called Reasons Why: The Very Best) and won a Grammy for This Side – a coveted trophy that Watkins reportedly put on top of his toilet at home.

"[citation needed]His sister Sara Watkins, also a member of Nickel Creek, plays violin and sings background vocals on the two latest of his three solo albums.

In 2004, Nickel Creek participated in a project dubbed Mutual Admiration Society, a collaboration with former Toad The Wet Sprocket singer Glen Phillips.

Bulla is no longer considered part of the group and as of summer 2011, their most recent lineup was Watkins and Phillips supported by Jerry Roe on drums and Sebastian Steinberg on bass guitar.

Keyboardist Benmont Tench (of Tom Petty and the Heartbreakers) and bassist Sebastian Steinberg (formerly of Soul Coughing) are regular participants and other guest musicians from the Largo family generally show up as well, including Jon Brion, Fiona Apple, Don Heffington, Greg Leisz, and former Nickel Creek bandmate Chris Thile when he is in town.

[7] Sean has also frequently supported his sister Sara on guitar and vocals for her solo dates since the release of her debut album in April 2009.