I love American Folk Music, especially when it’s done well. Iron and Wine is one of those where it’s close to perfect. It’s still flawed – from what I’ve heard there’s a bit much in repetition – but the potential is there. The man has a tendency to say, “This is a cool guitar lick” but then runs it over and over and over and sings to it. While not bad, the variance is in his voice, it sometimes makes the songs drag a bit. I would suggest listening to the previews on amazon.
I hate to admit it, but I heard him in the prom scene in TWILIGHT. Kelly loved it, I think it’s a cute but fairly strange Mormon fairy tale. (Protip: The vampires are the angels who chose to live among humans, the American Indians being called dogs is a slur, the rest is left as an exercise to the reader).
The song in TWILIGHT is Flightless Bird, American Mouth which isn’t his best work. Belated Promise Ring really shows off his stuff, but the band is only one guy, so he has to play all the instruments and harmonize with himself. He does have some free downloads on his site, I would suggest checking it out.