For someone who might find his later year voice, and the overly affected style of his music a bit off-putting, I would recommend the two volume complilations of "Early Year" recordings (recorded before his big commercial releases, but actually released much later). These simply arranged recordings highlight his song writing skills, which are prodigious, and are more listenable to those who are not his hardcore fans.
Tom Waits Bad?
Tom Waits has many a devoted fan. But since I began to haunt the audiophile sites, I've noticed a particular animosity, even cringing hate, directed toward the artist. I would be especially interested in the perspective of those who do not care for his craft. I know, curiosity kills...