Caricature of Sir William Lowther and Joseph Leeson, later Ist Earl of Milltown

Reynolds's caricature of Sir William Lowther and Joseph Leeson from 1751 belongs to the remarkable group of informal satirical drawings and paintings he produced during his Italian sojourn, an aspect of his character that his formal public career largely suppressed. Reynolds was in Rome and elsewhere in Italy between 1749 and 1752, and among the British Grand Tourists he encountered he produced a series of comic group portraits that circulated privately among their subjects. These Italian caricatures — influenced by the tradition of caricatura established by Annibale Carracci and developed by Pier Leone Ghezzi — demonstrate an observational wit and an informality that Reynolds's formal Grand Manner portraits rarely reveal. Leeson, who would become the 1st Earl of Milltown, was an Irish gentleman whose collection of Italian paintings eventually formed the core of the National Gallery of Ireland's holdings; the caricature thus connects the founding of two major institutions. Reynolds later theorized in the Discourses that caricature represented the lowest form of art — the antithesis of the generalized ideal beauty he championed — making these early works a fascinating document of the gap between his theory and his practice.

The caricature captures its subjects with humorous exaggeration. Reynolds's early drawing skill is evident in the witty characterization.