Too $hort, Maniac Lok

[PIMPIN' MADE EASY] It might be hard out there for a pimp, but over the course of his damn near 30 years in the rap game, Todd Anthony Shaw—better known as Too $hort—has made it look pretty dang easy. A winning insouciance has defined the 46-year-old Oakland MC's career, ever since he started slanging homemade mixtapes out the trunk of his car in the early '80s. Across the dozens of studio albums, EPs and collaborative tracks he's performed on, Shaw never exerts much of an effort, keeping his rhymes simple and his horndog lyrics one-track. It's not laziness, just good business strategy: In the oft-fickle world of hip-hop, sticking to one's guns—be they literal or metaphorical—is the key to longevity, especially when you've got a flow as adaptable as $hort Dog's. Through the years, Shaw has rhymed over everything from bare-bones 808 beats to Southern crunk to Bay Area hyphy to, on this year's No Trespassing, rock guitars, never compromising his personality. He might not have the lyrical prowess of, say, Rakim, but the guy knows exactly who he is and refuses to change, and that's what's made him a rapper's rapper.