Human Wheels
Back in the late 80s and early 90s you'd be hard pressed to find a bigger John Mellencamp fan than yours truly. I bought every album from the Johnny Cougar days right up until the late 90s - and even a couple imports. It was the release of Mr Happy Go Lucky (featuring "Key West Intermezzo") that finally soured my affections after years of tireless worship. I just didn't love it, and I haven't loved any efforts since. But the older albums continue to be mainstays in my iPod rotation.
If I were to rank my favorite albums from those days, I'd put Big Daddy and The Lonesome Jubilee at the top, but the it's the single Human Wheels from the album of the same name that has always been, to me, his finest work. I can't think of a song with more honest lyrics that capture the entire human experience.
Although I no longer consider myself an avid fan, Mellencamp's ability to withstand the test of time in the face of criticism, his unique sound, and his unwavering political convictions has always held my respect. And the fact that he's a Hoosier, and has continued to be a Hoosier, doesn't hurt.