Fabrizio De André

Despite living in Italy for more than two years now, I don't listen to very much Italian pop music. To be honest: most Italian pop music is really awful. It shares this property with most German pop music, by the way. But since we've been listening to more music at work recently (not because we're more lazy, but because we've improved our experiment in such a way that we can now play music without disturbing it), I've been exposed to more Italian music.
The one artist I've come to like is Fabrizio De André, a cantautore (singer-songwriter) who was active from the sixties up until his death in 1999. He has been compared to (and was influenced by) Bob Dylan and Leonard Cohen, both in his musical style (though he does enunciate much better than Dylan!), and in the importance of the texts in his work. It seems that his lyrics are sometimes taught in school nowadays, and certainly my Italian colleagues have a pretty good grasp of his most popular songs. Of course, the texts are also the area that I have difficulty with, since my knowledge of the Italian language is still lacking. There are however translations of some of his songs available, and for German-speaking readers, there's an entire website with line-by-line translations.
Many of his songs concern themselves with people at the edges of society: murderers, prostitutes, rebels, etc. Textwise, one of my favorites is "Carlo Martello ritorna dalla battaglia di Poitiers" ("Charles Martel on His Way Back from Poitiers"), a satiric song in which Martel is tricked by a prostitute, complete with archaic language and musical accompaniment on the harpsichord.
You can get an idea of his output by searching YouTube for some of his most popular songs: "Il testamento di Tito", "Il pescatore", "Andrea", "Fiume Sand Creek", "Creuza de mä". There are also two good compilations available: Blu and In Direzione Ostinata e Contraria.