Can white guys be hip? Many have tried but only a few have achieved true hepcat status - Bob Dylan, Lenny Bruce, maybe Jack Kerouac. But compare them to Miles Davis and you have to wonder if they're really just hipster wannabes. We'll dig into the history of hip, and see how it's so often tied into race. We'll also take another look at Bing Crosby. Today the crooner seems anything but hip. But back in the thirties Bing was the epitome of casual cool.