This tapestry is one of a set of six depicting scenes from the life of the Greek philosopher, Diogenes of Sinope (c.412–323 bc), one of the founders of Cynic philosophy. They were woven by the Mortlake manufactory that had been founded by James I and became the preeminent producer of English tapestry in the seventeenth century. The Mortlake mark of a St George Cross can be seen on the lower selvedge of this tapestry and on two others from the set, 'Diogenes and Plato' and 'Diogenes Beside his Barrel'. This set was almost certainly made for the Duke of York and probably hung in his apartments at Whitehall or St James's. A piece of canvas originally attached to one of the tapestries is marked with '6:ps, 11 FOOT DIOGENES' and the inscription 'DJ', the Duke of York's cipher. The tapestry depicting Diogenes beside his barrel also bears a later stamp on the reverse with a royal crown and IR for James II. As the 1674 inventory of the Duke of York's furnishings does not record these tapestries, they must have been made at some point between 1675 and Charles II's death in 1685.

A controversial figure in his time, the philosopher Diogenes argued that man should reject the conventional values of wealth, power and fame in favour of a simple and natural life. The tapestry depicts Diogenes meeting Alexander the Great, an encounter that is believed to have taken place in Corinth. The philosopher appears seated on the right at the mouth of the wooden barrel in which he lived, while Alexander, clad in rich armour, stands to the left with his attendants. The Latin inscription in the border identifies the incident and makes clear the moralising message: 'Alexander, when he saw in that urn its great inhabitant, felt how much happier was he who desired nothing, than one who demanded the world for himself.' The dismissive gesture made by Diogenes also illustrates his response when Alexander said 'Ask of me what thou wilt and thou shalt have it', to which he replied, 'Stand out of my light'.

Although the designer of the tapestries is not known, the source for the figures and inscriptions in four of the scenes is a series of etchings of 1662 by Salvator Rosa, though with the name of Diogenes substituting that of Democritus. Rosa's etchings of Democritus are based on his paintings of the early 1650s now in the Statens Museum for Kunst, Copenhagen. Given that the widest pieces in the series contain fine Italianate landscapes, the creator of these designs may have been a follower of Rosa in England, such as Henry Cooke (d. 1700), who studied under him in Italy, or Prosper Henricus Lankrink (d. 1692), who came to England in the 1660s and was noted both for having studied Rosa's work and for landscape.

Text adapted from the catalogue entry for Charles II: Art & Power

Sets at Weald Hall (with borders by Clein) and at Belton House follow the same design. The present set is likely to have been the first, Mortlake, weaving of which later sets were copies.