During the late 1490s, the Italian sculptor Guido Mazzoni submitted designs for the tomb of Henry VII at Westminster, although this scheme was eventually rejected in favour of his fellow Italian, Torrigiani. Mazzoni specialised in life-sized painted terracottas of the same strikingly realistic character as this example. The identification of this bust as a portrait of Prince Henry (the future Henry VIII) is supported by its royal provenance, unbroken since its creation, and the child’s apparent age. Its survival, in spite of its inherent fragility, and the richness of its decoration, imitating cloth of gold, also suggest that it held particular significance as a royal portrait. It is a most unusual aspect of this portrait, in that it depicts the sitter smiling, showing his teeth.