David Hockney, then emerging as one of Britain’s most important painters, is captured with Bailey’s frank directness. This compelling portrait demonstrates Bailey’s exceptional ability to capture creative personalities with psychological acuity, representing an amusing dialogue between two defining figures of British visual culture during their formative years.

The portrait belongs to Bailey’s broader documentation of London’s creatives, an ongoing series that includes his ‘Box of Pin-Ups’ portfolio, released in 1965. Collectively, this portfolio represents an unparalleled visual archive of Britain’s cultural renaissance during the 1960s. Here, Bailey captures Hockney before his relocation to California, a pivotal moment in the painter’s artistic development. The work connects two parallel artistic trajectories that profoundly shape contemporary visual culture, capturing the relationship between two creative forces that would each transform their respective fields.