Massimo Pericolo
After two years in prison, he gain popularity with one of the most cool song ever (7 miliardi). After that hit, every italian rapper wanted to write a song with him, and, trust me, for a good reason.
There is literally no one in Italy that does not know "Rozzi" or "Auto Tedesca". His career is similar to Massimo Pericolo's one, but his popularity is totally deserved. His debut album, dedicated to his dead uncle, has half the songs sad, the other half really aggressive, so there is always a song for every occasion.
He is the oldest one in the list, but there is a reason if he is called "King Marracash". No one can compete with his lyrics, and his album with Guè is still one of the most listened even today, after 8 years from its release. I personally did not like his last album, but some songs are such a hit.
He changed the history of italian rap music in recent years. He founded one of the most popular and game-changing musical group in the italian scene: "Machete crew". Maybe his recent songs are not that good as his firsts, but you have to listen to him at least once in your life if you want to talk about italian rap.
Probably the less known in this list. He is the co-founder of the Machete Crew with Salmo, but somehow he is less famous. Well, to be honest he usually sing in spanish, so that is probably the reason, but I think that is not enough to justify the fact that italian people usually ignore him.