Around the year 1508 or 1509, Titian painted an oil painting that is known as Christ Carrying the Cross. The actual origins of the painting are somewhat mysterious, and it has even been attributed at times by various historians of art to another Italian painter, Giorgione. Both painters were in an artists' guild that was connected to the school and the church, both were active in the same era and place, and it is likely that the work was painted expressly for the institution. Another mystery about the oil painting is that it was said to have miraculous curative abilities, having been written about in many historical narratives. Pilgrims would pray in the church at a side altar where the painting was hung, and reported being cured of ailments.

The overall mood of the work is somber and dark. The brightest colors are dull flesh-tones, and the palette is dominated by various shades of brown. Against an almost black background, Christ is shown in semi-profile carrying the cross on his shoulder. As he gazes off to the left, an angry looking executioner tightens a noose of rope around his neck, and another figure slightly behind the executioner looks inwards behind the scene. The composition is in a style that was innovative at the time, a close-up view that eschewed perspective and depth for intimacy and detail. Characteristically for Titian, the painting is full of action, and repose seems far away for the characters depicted.