I put Jolie Holland in the same class as Bob Dylan and Tom Waits because of her ability to assimilate traditional music into a sound and style that is singularly her own. She also happens to have an unusual voice that, not unlike Bob Dylan and Tom Waits, doesn’t exactly have mass appeal. One reviewer said she sings like she’s got a mouth full of marbles. Maybe, but she makes it work. Her music first fell into a folky weird bluesy category and has gradually moved towards a more full-on band rock sound, kinda like Bob Dylan. Every album builds on what came before it and, although she doesn’t hit pay dirt every time, it’s usually pretty damn good. The first song of hers to grab me was the ghostly Wandering Angus. Her interpretation of Pure Imagination is way out there too. But I’ll pick “Mexico City” because I don’t know what else to pick.
P.S.: The Daytrotter Sessions from 2007 and 2009 are essential Jolie Holland recordings, perhaps more so than any of her albums. It’s the best sample of her music I’ve found online. Wolfgang’s Vault has performances of some of her latest songs.