Producer: Def Jef
Album: Born Gangstaz
Label: Def Jam

Bo$$ was arguably the first female gangster rapper, but she became something of a lightning rod when it was revealed in a 1994 Wall Street Journal article that she'd attended private school and been raised in an upper middle class family. Her parents were even reportedly sending her money after she moved from Detroit to Los Angeles to pursue her recording career. That ain't gangsta. Still, the lie was fun while it lasted, and "Deeper" was a strong cut.