Around 1857 Simeon Solomon (age 16) was introduced by Dante Gabriel Rossetti (age 28) to members of the Pre-Raphealite Brotherhood including Algernon Charles Swinburne (age 19) and Edward Coley Burne-Jones 1st Baronet (age 23).

In 1858 Simeon Solomon (age 17) exhibited at the Royal Academy.

The Diary of George Price Boyce 1858. 13 Feb 1858. February 13. Miss Cooke came to sit for me. Little Simeon Solomon (age 17) called and stayed a long while and jawed and bored us considerably. Burges came up and I introduced them.

1859 to 1863. Simeon Solomon (age 18). "Dante's First Meeting with Beatrice".

1859. Simeon Solomon (age 18). Self-Portrait.

1859. Simeon Solomon (age 18). "Pastoral Lovers".

1859. Simeon Solomon (age 18). "Babylon hath been a golden cup". Pen and ink. One of the illustrations for the "Bible Gallery", a hundred-print collection of engravings conceived by the brothers Dalziel in 1859. This drawing depicts the Jewish King David and the maiden, Abishag, looking concerned and androgynous, and illustrates a passage in Jeremiah lamentating the Jewish people's captivity by the kingdom of Babylon: 'Babylon hath been a golden cup in the hand of God, which hath made all the earth drunken: the nations have drunken of her wine, therefore all the nations are mad.' The drawing was considered too risque for the Bible Gallery, and was exhibited separately at the French Gallery Winter Exhibition in 1859.