If Too $hort didn’t invent the laidback, dog-eat-dog pimp persona that defined gangsta rap, he was certainly one of the first to take it nationwide. He’s never been a flashy rapper—if anything, he keeps things simple even as the genre evolves. But there’s a confidence in his simplicity, not to mention a purity of intention: He’s here to make money and get women in terms that could make your shadow blush. A nice guy? Not really. (He once joked that his greatest contribution to popular culture was bringing the word “bitch” into rap.) But like Iceberg Slim and Redd Foxx before him, you can trust him to never sugarcoat it. Funky, lean, and matter-of-fact, here’s the best of the Short Dog.