Lupe Fiasco about the album cover of "The Cool" in a Pitchfork interview 2007:
They’ve got supernatural characteristics. Like the Cool, his right hand is rotted away. The only thing that rotted away was his right hand. It represents the rotting away of his righteousness, of his good. And the Streets and the Cool kind of have a love affair going on. So she’s represented by this locket. And the locket has a key and it’s on fire. And as a gift to the Cool on his rise to fame, she gave him the key. And the key represents the key to the Streets.
So she wears a locket around her neck at all times. And the way the story goes, she has given that key to tons of people throughout time. Al Capone, Alexander the Great, whatever. She’s giving them the key to the Streets. Fame and fortune– but also the prices. The Game, he’s represented by a stripped-down skull, a skull with dice in his eyes and smoke coming out of his mouth. The billowing smoke is actually crack smoke.