Rebecca Mead, writing in The New Yorker, uses Ira Glass' tweet declaring "Shakespeare sucks" as the starting point to explore whether relatability is relevant to works of art: 

What are the qualities that make a work “relatable,” and why have these qualities come to be so highly valued? To seek to see oneself in a work of art is nothing new, nor is it new to enjoy the sensation. Since Freud theorized the process of identification—as a means whereby an individual develops his or her personality through idealizing and imitating a parent or other figure—the concept has fruitfully been applied to the appreciation of the arts. Identification with a character is one of the pleasures of reading, or of watching movies, or of seeing plays, though if it is where one’s engagement with the work begins, it should not be where critical thought ends. The concept of identification implies that the reader or viewer is, to some degree at least, actively engaged with the work in question: she is thinking herself into the experience of the characters on the page or screen or stage.

But to demand that a work be “relatable” expresses a different expectation: that the work itself be somehow accommodating to, or reflective of, the experience of the reader or viewer. The reader or viewer remains passive in the face of the book or movie or play: she expects the work to be done for her. If the concept of identification suggested that an individual experiences a work as a mirror in which he might recognize himself, the notion of relatability implies that the work in question serves like a selfie: a flattering confirmation of an individual’s solipsism.