The present article sought to provide a comparison between The Sophoclean Trilogy and King Lear, respectively produced by Sophocles in the 5th century BC Greece and by William Shakespeare in 1606 at the end of the Elizabethan era in Britain. The comparison was set to investigate the two playwrights’ adherence to the production of a good tragedy such as the one Aristotle described in his Poetics. Another attempt was to explain how tragedy evolved during Elizabethan times and measure the extent of deviation both from Aristotle’s and Sophocles’ conception of some essential tragic factors relating mostly to the hero’s hamartia and fall, learning and recognition, fate and free will, retribution and redemption, in addition to diction and style. As the comparison showed, some changes were, indeed, made in the tragedy of King Lear, namely at the level of form, including, among others, the division of the play into separate Acts and Scenes, the breaking of the unity of Action, the increase of the number of characters, etc. At the level of content, the changes appear to have equally touched some important issues, namely the role of fate and prophecies, the characters’ flaws, in addition to the nature of the relation between family members, to mention but a few changes. At a deeper level, however, Shakespeare’s tragedy mostly remained faithful to its classical heritage, namely through the punishment of the bad and the gratifying of the good. The gods were always omnipresent and ready to reestablish the status quo, restore justice and bring back prosperity and peace, though sometimes in an incomprehensible way, especially when their action was coupled with fate and bad fortune.