O'Donovan and DiMario met at the New England Conservatory of Music in Boston, Massachusetts in spring of 2001. Former cellist Rushad Eggleston, who was studying at Berklee College of Music, and Liszt, a graduate student at MIT, were playing music together around the same time. When the four met that summer, they formed the band that would be Crooked Still. While its members finished school, Crooked Still played various Boston venues, growing in popularity and collecting favorable reviews from the local press, notably the Boston Globe, Northeast Performer, and the Boston Herald.
In 2004, the group was invited to perform at the Newport Folk Festival and Falcon Ridge Folk Festival, where their debut album, Hop High, was the top-selling CD. Following the success of this first festival appearance, Crooked Still went on to appear at concert halls, nightclubs, coffeehouses, and festivals in 23 states and several different countries. On August 22, 2006, they released their second CD, Shaken by a Low Sound.
In October 2007 the band announced that Eggleston would be leaving the group. Eggleston performed his last show with the band on November 18, 2007, at the Ironhorse in Northampton, Massachusetts. Cellist Tristan Clarridge and fiddler Brittany Haas joined the lineup in January 2008. The band released its first album with the new lineup, Still Crooked, in June 2008. bluegrass folk americana female vocalists seen live