Former Bad Boy superstar Shyne surprised many when he converted to Judaism during his eight-year prison bid. Since his release, he's been seen sporting Jewish garb in Israel, letting his beard and sideburns grow, and at times renouncing his gangster-rap roots in favor of his new religious path. On August 1, he unveiled a new song, "King Crown of Judah," featuring Hasidic rap-reggae singer Matisyahu, which addresses his faith and conversion head on. We're not sure why people have been that surprised though — hip hop and Judaism have been crossing paths for years now. Click on for a look at some of the most prominent Jews in rap.