Well, though I'm italian, i'm not a great fan of italian music, excepts for the lyrical operas, but I can give you some suggestions.
If I had to choose my favourite songs I'll take something from De Andrč, Guccini, Modena City Ramblers, Timoria and Litfiba.
I like very much the first record from Elisa pipes and flowers" but she sings in English there.
If you want something more contemporary you can listen to Laura Pausini, Giorgia and Ramazzotti (above all the old records), or you can take a look at the last editions of the songs from the sanremo festival or try on google "migliori canzoni italiane", you will surely find some inspiration!
anyway, here's a little list from my favourites in random order:
In morte di S.F. (canzone per un'amica) - Guccini/ Nomadi
Auschwitz - Guccini/ Modena City Ramblers
La guerra di Piero - De Andrč
Dio č morto - Guccini
Fischia il vento - Modena city Ramblers
Io vagabondo - Nomadi
L'unica superstite - Modena City Ramblers
Sangue impazzito - Timoria
Anja del settimo cielo - Grazia di Michele
Il guardiano di cani - Timoria
I cento passi - Modena City Ramblers
Carlo Martello torna dalla battaglia di Poitiers - De Andrč
Il testamento di Tito - De andrč
Gioconda - Litfiba
Don Chisciotte - Guccini
In un giorno di pioggia - Modena City Ramblers
Transamerika - Modena City Ramblers
El Diablo - Litfiba
Luce - Elisa
Lettera al futuro - Ramazzotti ( i like that because is inspired by "The masque of the Red Death" by Poe)
"-Please tell me you're going to appeal to my humanity..."
"-Actually, I'm planning to threaten you."
"Well, if you'll excuse me, I have work to do. Evil plots don't just make themselves, you know!"