As the Earl of Essex unrestfully sat in house arrest in the spring of 1600, he penned a plea to his sovereign Queen in which he begged forgiveness for the sake and salvage of his legacy. He wrote, “Already they print me and make me speak to the world, and shortly they will play me in what forms they list upon the stage, the least of which is a thousand times worse than death.” Essex, who led an eventful life as a favorite of the court and of Queen Elizabeth, ultimately was executed for leading an unsuccessful uprising against the Queen. Essex very deftly anticipated his painful legacy, for the earl has indeed been portrayed in paintings, plays, music, poetry, opera, fiction, and various documents spanning four centuries since his death in 1601. Our scholarly project, a thanatography of Essex that takes the form of a digital timeline, attempts to elucidate viewers as to the variety of representations of Essex, from his famed arrogance, to his plunders and pitfalls as a soldier, even to his often romanticized and sometimes scandalously fictionalized relationship with Elizabeth. The examination and analysis of the various ‘afterlives’ of Essex provide the viewer of the timeline with a window into the culture and time period in which a work was written or composed, and thus explores and attempts to realize the wondrous and ever-changing way in which human beings tell stories.