Boswell was born in Blair’s Land on the east side of Parliament Close behind St Giles’ Cathedral in Edinburgh on 29 October 1740 (N.S.). He was the eldest son of a judge, Alexander Boswell, Lord Auchinleck, and his wife Euphemia Erskine. As the eldest son, he was heir to his family’s estate of Auchinleck in Ayrshire. Boswell’s mother was a strict Calvinist, and he felt that his father was cold to him. As a child, he was delicate. Kay Jamison, Professor of Psychiatry at Johns Hopkins, in her book Touched with Fire, believes that Boswell may have suffered from bipolar disorder, and this condition would afflict him sporadically all through his life. At the age of five, he was sent to James Mundell’s academy, an advanced institution by the standards of the time, where he was instructed in English, Latin, writing and arithmetic.

Boswell was initiated into Freemasonry in Lodge Canongate Kilwinning on 14 August 1759. He subsequently became Master of that Lodge in 1773 and in that year was Senior Grand Warden of the Grand Lodge of Scotland. From 1776 to 1777 he was the Depute Grand Master of that Grand Lodge.

On 30 July 1762, Boswell passed his oral law exam, after which his father decided to raise his allowance to £200 a year and permitted him to return to London. In this period, Boswell wrote his London Journal and, on 16 May 1763, met Johnson for the first time. The pair became friends almost immediately, though Johnson became more of a parental figure in Boswell’s eyes. Johnson eventually nicknamed him “Bozzy”.

Boswell returned to London in February 1766 accompanied by Rousseau’s mistress, with whom he had a brief affair on the journey home. After spending a few weeks in the capital, he returned to Scotland, buying (or perhaps renting) the former house of David Hume on James Court on the Lawnmarket. He studied for his final law exam at Edinburgh University. He passed the exam and became an advocate. He practised for over a decade, during which time he spent no more than a month every year with Johnson. Nevertheless, he returned to London annually to mingle with Johnson and the rest of the London literary crowd, and to escape his mundane existence in Scotland. He found enjoyment in playing the intellectual rhyming game crambo with his peers.

The comedy Young Auchinleck (1962) by Scottish playwright Robert McLellan depicts Boswell’s various courtships and troubled relations with his father in the period after his return to Scotland in 1766, culminating in his eventual marriage to his cousin Margaret Montgomery (Peggy) in 1769 on the same day as his father’s second marriage in a different part of the country. The play was first produced at the Edinburgh International Festival in 1962 and adapted for BBC Television in 1965.

Some of his journal entries and letters from this period describe his amatory exploits. Thus, in 1767, in a letter to William Johnson Temple, he wrote, “I got myself quite intoxicated, went to a Bawdy-house and past a whole night in the arms of a Whore. She indeed was a fine strong spirited Girl, a Whore worthy of Boswell if Boswell must have a whore.” A few years earlier, he wrote that during a night with an actress named Louisa, “five times was I fairly lost in supreme rapture. Louisa was madly fond of me; she declared I was a prodigy and asked me if this was not extraordinary for human nature.” Though he sometimes used a condom for protection, he contracted venereal disease at least seventeen times.

Boswell was a major supporter of the Corsican Republic. Following the island’s invasion by France in 1768, Boswell attempted to raise public awareness and rally support for the Corsicans. He sent arms and money to the Corsican fighters, who were ultimately defeated at the Battle of Ponte Novu in 1769. Boswell attended the masquerade held at the Shakespeare Jubilee in Stratford-upon-Avon in September 1769 dressed as a Corsican Chief.

Boswell married his cousin, Margaret Montgomerie, in November 1769. She remained faithful to Boswell, despite his frequent liaisons with prostitutes, until her death from tuberculosis in 1789. After his infidelities, he would deliver tearful apologies to her and beg her forgiveness, before again promising her, and himself, that he would reform. James and Margaret had four sons and three daughters. Two sons died in infancy; the other two were Alexander (1775–1822) and James (1778–1822). Their daughters were Veronica (1773–1795), Euphemia (1774 – c. 1834) and Elizabeth, known as ‘Betsy’, (1780–1814). Boswell also had at least two extramarital children, Charles (1762–1764) and Sally (1767 – c. 1768).

In 1773 Boswell bought the house of David Hume (who moved to a new house on South St David Street/St Andrew Square) on the south east corner of James Court. He lived there until 1786. Boswell’s residency at James Court has been well established, but not the exact location. For example, a later edition of Traditions of Edinburgh by Robert Chambers suggests that Boswell’s residence at James Court was actually in the Western wing. His James Court flat was notable for having two levels, and although a modern renovation in the Eastern section reveals such a possibility, it is likely that Boswell’s residence was a similarly equipped one in the Western section that no longer exists, having burned down in the mid 1800s.

After Johnson’s death in 1784, Boswell moved to London to try his luck at the English Bar, which proved even less successful than his career in Scotland. In 1792 Boswell lobbied the Home Secretary to help gain royal pardons for four Botany Bay escapees, including Mary Bryant. He also offered to stand for Parliament but failed to get the necessary support, and he spent the final years of his life writing his Life of Samuel Johnson. During this time his health began to fail due to venereal disease and his years of drinking. Boswell died in London in 1795. Close to the end of his life he became strongly convinced that the “Shakespeare papers”, including two previously unknown plays Vortigern and Rowena and Henry II, allegedly discovered by William Henry Ireland, were genuine. After Boswell’s death they proved to be forgeries created by Ireland himself. Boswell’s remains were interred in the crypt of the Boswell family mausoleum in what is now the old Auchinleck Kirkyard in Ayrshire. The mausoleum is attached to the old Auchinleck Kirk.

Boswell was present at the meeting of the Committee for the Abolition of the Slave Trade in May 1787 set up to persuade William Wilberforce to lead the abolition movement in Parliament. However, the abolitionist Thomas Clarkson records that by 1788 Boswell “after having supported the cause … became inimical to it”. Boswell’s most prominent display of support for slavery was his 1791 poem “No Abolition of Slavery; or the Universal Empire of Love”, which lampooned Clarkson, Wilberforce and Pitt. The poem also supports the common suggestion of the pro-slavery movement, that the slaves actually enjoyed their lot: “The cheerful gang! – the negroes see / Perform the task of industry.”

When the Life of Samuel Johnson was published in 1791 it at once commanded the admiration that Boswell had sought for so long, and it has since suffered no diminution. Its style was unique in that, unlike other biographies of that era, it directly incorporated conversations that Boswell had noted down at the time for his journals. He also included far more personal and human details than those to which contemporary readers were accustomed. Instead of writing a respectful and dry record of Johnson’s public life in the style of the time, he painted a vivid portrait of the complete man, brought to life through a “dramatic” style of dialogue. It has often been described as the greatest biography ever written.

In the 1920s a great part of Boswell’s private papers, including intimate journals for much of his life, were discovered at Malahide Castle, north of Dublin. These provide a hugely revealing insight into the life and thoughts of the man. They were sold to the American collector Ralph H. Isham and have since passed to Yale University, which has published popular and scholarly editions of his journals and correspondence. A second cache was discovered soon after and also purchased by Isham. A substantially longer edition of The Journal of a Tour to the Hebrides was published in 1936 based on his original manuscript, edited by L. F. Powell. His London Journal 1762–63, the first of the Yale journal publications, appeared in 1950. The last popular edition, The Great Biographer, 1789–1795, was published in 1989. Publication of the research edition of Boswell’s journals and letters, each including never before published material, is ongoing.

On November 14 2020, New York Times columnist Maureen Dowd called reporter Maggie Haberman “Trump’s Boswell”, referring to Ms. Habermans tenacious and in depth reporting of Donald Trumps presidential years.