Crooked County started in 1997-ish after Toby Purnell and Kurt Squire met in The Mary Janes, and played a few shows with the short-lived bluegrass band, Big Mule. Toby bought a Telecaster, got Mark Minnick to bring his Waylon inspired drum beats, and they went country. The first album, Whiskey Burns was recorded in 1998-1999 at Farm Fresh studios by Jacob Belser and featured songs by Toby and his brother Jason's. Whiskey Burns included inspired performances from many in Bloomington's music scene, including Janas Hoyt, Jeff Farias, Dennis Scoville, Megan Weeder, and the Not Too Bad Bluegrass Band. Merrie Sloan closed down the CD release after-party, and soon she was in the band, as was Travis Olsson. Jeff Farias recorded their second release, Drunkard's Lament for Rustic Records.