[2][3][4] O'Donovan states that the band is playing its "own sort of continuation" on the bluegrass tradition that began in the U.S. with Bill Monroe and Jimmy Martin.

While its members finished school, the group played various Boston venues, growing in popularity and collecting favorable reviews from the local press.

In January 2008 two new members joined the band: cellist Tristan Clarridge and fiddler Brittany Haas, both of whom have toured in Darol Anger's Republic of Strings.

In honor of their tenth anniversary together as a band, Crooked Still embarked on a major tour of the Northeast and the Pacific Northwest, and released a 7-song EP called Friends of Fall in October 2011.

In June 2018, Crooked Still songs "Little Sadie" and "Ecstasy" were featured in the gameplay trailer for The Last of Us Part II presented at E3 2018.