The late 1950s was a successful period of the artist’s career. With a number of successful exhibitions at Gallery One under his belt, and with the patronage of wealthy US businessman Harold Kovner in full swing, Souza was financially stable and able to embark on more ambitious artistic projects. In 1958 Souza was selected as one of five painters, alongside Ben Nicholson, John Bratby, Terry Frost and Ceri Richards to represent Great Britain in the Guggenheim International Award, exhibiting his monumental painting Birth.

Head of a Man in Glasses was painted in Barcelona, and is mentioned in a letter the artist writes to his dealer Victor Musgrave, in November 1958:

“Dear Victor, I am leaving for Palma tomorrow evening after spending about a week here... I like Barcelona, though, and I hope to return frequently… I have managed to do one painting last night. It’s a head of a man with glasses. It’s painted on canvas. I think I’ll paint mainly on canvas from now although it is five or ten times more expensive than hardboard… I will have to leave the painting I did in the hotel, but I’m seeing to it that it is not lost...”
FN Souza’s letter to Victor Musgrave, 6 November 1958

Happily, the painting was not lost, and returned shortly afterwards to the UK, where it was acquired by a Doctor and his wife. It has remained in the family collection since then. Souza wrote to the original owners in October 1961, discussing his upcoming exhibition at Gallery One; “My recent work which I brought back from Spain is quite terrific and sensational.” Copies of both letters are held at the gallery.