In 1756 Johnson was arrested for a debt of nearly £6, which was resolved in the form of a loan from the writer and publisher Samuel Richardson. Financial hardship continued and he was arrested again in 1758 for a debt of £40, which was paid off as an advance on an edited book of Shakespeare plays that Johnson planned. When his mother died in 1759 he only managed to pay her funeral expenses and debts by obtaining an advance on a new novel, The Prince of Abissinia, which he quickly completed.
Johnson had an outstanding talent for retaining information and vocabulary, much of it acquired from the large number of books he read. In addition to his writing he was extremely eloquent and began to gain a reputation as a raconteur, full of information, opinion, anecdotes and with a quick wit. He loved nothing better than to spend evenings in taverns around Fleet Street, drinking tea or lemonade, discussing issues into the early hours of the morning. He delighted in debate and would happily argue one opinion or another, whichever was the opposite of that taken by others around him. Johnson cared little with whom he sat and debated provided they could bring companionship, interesting knowledge, and opinions to the table. The artist Joshua Reynolds once noted that if Johnson was ever left out of the conversation, “His mind appeared to be preying on itself; he fell into a reverie accompanied with strange antic gesticulations.” As his reputation as an orator grew he was often sought out by those with a literary interest who wished to meet him. His speech was so clever and witty that his observations were often memorised and repeated by those who met him. He gradually became somewhat of a celebrity, welcomed at dinner parties in the homes of literary society, and his activities widely reported in newspapers.
In order to ensure regular evenings of conversation Johnson founded a club at which a small number of suitable colleagues met weekly during the 1740s at the King’s Head beef-steak house at Ivy Lane, near St. Paul’s. Other places that Johnson frequented were the Mitre tavern in Fleet Street, the Turk’s Head in the Strand and Old Slaughter’s coffee house in St. Martin’s Lane. Although never prosperous, he managed to survive financially and his wealthier friends were generous towards him with their hospitality. In turn he supported less-fortunate people he met, some of whom he took into his household, in part because he delighted in the company of others, so long as they could provide good conversation.
From 1762 Johnson became more financially stable when he was unexpectedly granted a pension of £300 per year by King George III in recognition of his work in producing the Dictionary. He was initially reluctant to accept, believing it would put him in the pocket of others. His close friend Joshua Reynolds was by then quite wealthy from the many portraits he was painting and had just purchased a large house and studio at Leicester Square, across from William Hogarth. Johnson visited him there for advice and was told to accept. He also visited the leading minister, Lord Bute, to thank him and was assured the offer was purely for what he had achieved. Johnson never became wealthy but at least from then he had a stable income for the remainder of his life.
In the summer of 1763 a new companion joined Johnson’s circle of friends: the young Scotsman, James Boswell. His primary aim in coming to London was to seek out the town’s literati to hear what they had to say first-hand. Within weeks of his arrival he had socialized with many of London’s fashionable elite, from the Prince of Mecklenburg to David Garrick. Amongst Johnson’s many dislikes were Scottish people, so Boswell’s first nervous words to the great man, as quoted in his The Life of Samuel Johnson, were: “I do indeed come from Scotland, but I cannot help it,” to which Johnson replied in his typical way “Sir, that, I find, is what a very great many of your countrymen cannot help.” From their earliest meetings the Scotsman began to record in writing Johnson’s many interesting pieces of information and quips. Later, when Johnson was in his mid-sixties, the two companions made a tour on foot and horseback around Scotland, often along rugged mountain tracks.
In 1763 Reynolds proposed to Johnson the creation of a formal group of friends, similar to Johnson’s Ivy Lane club of 20 years earlier, which would meet every Monday evening to dine and debate at the Turk’s Head tavern at Gerard Street in Soho. Over the following decade the Club grew in prestige and membership was highly sought-after, with potential members lobbying for inclusion.