The Droeshout engraving

The very thing that leads so many scholars and Shakespearianists to despise this portrait--it's cartoonishness--is the very thing that makes it so perfect a portrait of Shakespeare. Not that Shakespeare was cartoonish, exactly; but rather than this cartoony mode enables us to identify with the Shakespeare myth: namely that, whilst he is is of course a genius and far above us, he is at the same time, somehow, ordinary, usual, he is us. Jonathan Franzen has this to say about the appeal of cartoons:

Scott McCloud, in his cartoon treatise Understanding Comics, argues that the image you have of yourself when you’re conversing is very different from your image of the person you’re conversing with. Your interlocutor may produce universal smiles and universal frowns, and they may help you to identify with him emotionally, but he also has a particular nose and particular skin and particular hair that continually remind you that he’s an Other. The image you have of your own face, by contrast, is highly cartoonish. When you feel yourself smile, you imagine a cartoon of smiling, not the complete skin-and-nose-and-hair package. It’s precisely the simplicity and universality of faces, the absence of Otherly particulars, that invite us to love them as we love ourselves.