Caricature of Sir Thomas Kennedy, James Caulfield, Viscount Charlemont, the Hon. John Ward and Richard Phelps

Reynolds's 1751 Caricature Group depicting Sir Thomas Kennedy, Viscount Charlemont, the Hon. John Ward, and Richard Phelps was painted during the artist's formative stay in Italy, where he encountered the tradition of caricature touring portraits pioneered by Pier Leone Ghezzi and practiced by Arthur Pond and others among the British Grand Tourists. These comic group portraits satirized the posturing and pretension of young Englishmen abroad while remaining affectionate enough to function as souvenirs of friendship. Reynolds produced several such works in Rome and Naples, using them to cultivate the patronage networks that would launch his London career.

The caricature format allows Reynolds a freedom absent from formal portraits: features are exaggerated, poses slightly absurd, expressions animated. Despite the comic intent, the paint handling is accomplished, with loose, confident strokes suggesting gesture and character. The group is informally arranged, conversation implied.