Reynolds worked principally in portraiture, a division of the art of painting that he regarded as inferior to others. Doctor Johnson said of Reynolds that so equable was his temper that he was the most invulnerable man he knew because it was impossible to find anything with which to reproach him. Yet Reynolds was suspected of being an opportunist toady, a flatterer of the rich, famous, and powerful, whom, by and large, he painted—in the process becoming rich, famous, and powerful himself. Though Reynolds was undoubtedly both keen on money and disagreeably penny-pinching toward relatives and assistants, no man who became a close friend of Doctor Johnson, Edmund Burke, Oliver Goldsmith, and Edward Gibbon could have been a nonentity with merely a talent for flattery. Boswell tells the story of how Johnson and Reynolds became friends:
When Johnson lived in Castle Street . . . he used frequently to visit two ladies who lived opposite him, Miss Cotterells, daughters of Admiral Cotterell. Reynolds used also to visit there, and thus they met. . . . Sir Joshua, indeed, was lucky enough at their very first meeting to make a remark which was so much above the commonplace style of conversation, that Johnson at once perceived that Reynolds had the habit of thinking for himself. The ladies were regretting the death of a friend to whom they owed great obligations; upon which Reynolds observed, “You have, however, the comfort of being relieved from a burden of gratitude.” They were shocked a little at this alleviating suggestion . . . but Johnson defended it in his clear and forcible manner and was much pleased with the mind, the clear view of human nature, which it exhibited.
Johnson and Reynolds were close friends ever after, and Boswell dedicated his great Life to the painter. Reynolds’s “clear view of human nature” is evident in his best portraits, which penetrate the character of his sitters, while also remaining surface likenesses. The fact that he painted several people serially suggests that he was more than just a society portraitist (though he was that as well). The several portraits of Doctor Johnson, for example, do not make out that the great writer was a handsome or an elegant man and do not in the slightest seek to lessen his peculiarities—but the force of his character, the intensity of his thought, and the profundity of his religious and emotional struggles are conveyed with extraordinary clarity. Though Reynolds’s veneration of Johnson could not have been greater (it was, unusually for a relationship of veneration, entirely mutual), Reynolds did not think of Johnson as a saint; far from it. In the character sketch that Reynolds provided for Boswell when he was writing Life, the painter said:
The drawback to his character is entertaining prejudices on very slight foundation, giving an opinion perhaps first at random, but from its being contradicted he thinks himself always obliged stubbornly to support. . . . He thought it necessary never to be worsted in argument, though this disposition he spoke of as very weak; “as if,” says he, “the character depended on one evening.” He thus seemed to be schooling himself, but he never learned the thing.
Reynolds continued: “You will wonder to hear a person who loved him so sincerely speak thus freely of his friend, but you must recollect I am not writing his panegyric, but as if on oath not only to give the truth but the whole truth.” Here, then, was a man who could revere without blindness, who understood that even the greatest were not without flaws, but that the flaws did not obviate the greatness.
-- Theodore Dalrymple (http://www.city-journal.org/2016/26_1_art.html)