During these years Johnson remains busy as a writer and attempts to procure a performance for Irene. He writes magazine essays, poetry (including “Friendship: An Ode”), and biography, including a life of the colorful and roguish poet Richard Savage, with whom Johnson lived for some time in London in poverty. In another section that shows Boswell taking pains to demonstrate his independence of mind and objective approach to his subject, Boswell comes close to condemning this period of Johnson’s life. Boswell implies that associating with the outlaw Savage introduced Johnson to the “dissipation and licentiousness” (119) of London’s underworld and for a time tempted him away from a virtuous lifestyle. This accusation is quite bold, given how little is known about Johnson’s relationship with Savage—Boswell’s characterization becomes the de facto truth about Johnson’s dissipations. 

In this same period, Johnson produces a monograph on Shakespeare’s Macbeth; Johnson will become particularly known for his critical observations on Shakespeare and will be considered one of the major Shakespearean commentators.

Boswell recounts an anecdote involving Johnson and two other major artistic figures of the day: the novelist Samuel Richardson and the artist William Hogarth. Richardson and Hogarth are talking politics in Richardson’s house when suddenly Johnson appears at the window “shaking his head, and rolling himself about in a strange ridiculous manner” (107).