For more than fifty years, Rolling Stone magazine has been the defining voice in musical journalism. Alongside its timeless cover images and groundbreaking criticism, the magazine's illustrations – like the caricatures and cartoons of great satirical and political publications before it – have given popular culture a new iconography. Drawing on five decades of the magazine's archives, but with a focus on more contemporary artists and issues, this stunning book collects more than 200 of the most characterful and iconic portraits of major cultural figures of recent times – from Bob Dylan to Barack Obama, Oprah to Madonna. Some of the greatest names in art and design have come to define the magazine's illustrated lexicon, from heroes of the twentieth century like Milton Glaser and Ralph Steadman to subversive contemporary artists such as Christoph Niemann and Mark Ryden. Organised not chronologically but by pairing images by theme or connection – Richard Nixon facing Donald Trump, or Frank Ocean with Jimi Hendrix – and with anecdotes from some of the artists and subjects alongside the images themselves, the book presents a whimsical illustrated history of contemporary culture filtered through the Rolling Stone lens.