This chapter argues that Charlotte Lennox challenged the orthodoxies of her time in a number of ways. She not only made a career for herself as an intellectual and published writer, at a time when it was still relatively rare for women to do this, but she also ventured into the male-dominated and prestigious genre of Shakespeare criticism. She was probably born in 1729 or 1730 in Gibraltar, where her father, James Ramsay, was serving as an officer in the British army. Lennox learned Italian in order to undertake the Shakespear Illustrated project. Her tutor was called Giuseppe Baretti, and he worked very closely with her on her translations. In many instances, Lennox argues straightforwardly for the superiority of Shakespeare's Italian sources to his plays. Clearly, Lennox can be accused of judging the plots and characters of Shakespeare's romantic comedies, and late Romances in particular, by the standards of a later, more realistic or naturalistic mode of writing.