This paper deals with Freud's longstanding fascination with the true identity and authorship of Shakespeare. After reading J. Thomas Looney's book, Shakespeare Identified, in 1923 he became convinced, like Looney, that Edward de Vere, the seventeenth Earl of Oxford was the true author of Shakespeare's plays and poems. Looney's position is examined and compared with the arguments subscribing authorship to the humble bard of Stratford. The change in Freud's belief in support of Looney's is attributed to a form of family romance fantasy in Freud himself. In addition, Looney's manner of drawing conclusions about authorship and biographical data from the plays is similar to an important cognitive style employed by Freud.