This painting is a double self-portrait of the artist. In the background, a young Peter Blake stands carrying an oversized Valentine’s Day card intended for the artist Pauline Boty. Boty was Blake’s friend and contemporary. She was a founder of British Pop Art and the only woman artist in the British faction of the movement.

The self-portrait in the foreground demonstrates that Blake’s romantic feelings for Boty have not been reciprocated. If you look closely, there is a small tear in the corner of his eye. This tear is also prophetic of Blake’s sadness following the death of Boty in 1966, seven years after this painting was completed. Boty died at the tragically young age of 28 from cancer. She refused treatment as she was pregnant at the time.

The Valentine’s Day card image in this painting appears later in Blake’s Love Wall and in the design for Motif in 1962. The black and white striped area to the right of this painting is a homage to the pedestrian crossing picture painted by Blake’s contemporary Brian Young. However, this heraldic device is typical of Blake’s work, and is incorporated into his later Pop pictures including Tuesday. Boy with Paintings bears a resemblance to On the Balcony (1955-57) in style and content, as well as Self-Portrait with Badges (1961). This last painting depicts the artist a couple of years later dressed in clothes inspired by American culture.

Peter Blake was a highly influential and original artist. He is often described as the godfather of British Pop Art. At the core of Blake’s work is an ever-present fascination with the world of popular culture and entertainment, including music, film and sports. His pioneering images of the 1950s and 1960s, including Self-Portrait with Badges (1961) and The Beatles (1963–8), are iconic both within art history and popular imagination.