The painter Bruegel surfaces for the first time in 1551, though admittedly as an archival footnote. He paints the exterior panels of an altarpiece in Mechelen that has gone lost. The first dated paintings following this date only from 1557: Landscape with the Parable of the Sower (Timken Art Gallery, San Diego) and The Drunk Cast into the Pigsty (private collection) are attributed to the master. Up until 1561, only five paintings have survived. More than likely a number of works have gone lost, but it also seems highly likely that Bruegel primarily showed up as a draughtsman or print artist in that time. Bruegel, a master draughtsman and an accomplished miniaturist and print artist, appeared to originally encounter difficulties with certain points within the medium of painting. He was an experienced maker of small works on paper and had to adjust himself to larger work that had to be appreciated at a distance. At the painting technical level he seems to be searching and avails himself to a number of different manners of painting in this period.
After this beginning period as a painter he decreases the number of prints and Bruegel fully choses for a life as a painter. In 1561 and 1562 various masterpieces come to light: Dulle Griet(Museum Mayer van den Berg), The Triumph of Death (Museo del Prado, Madrid), The Archangel Michael Slaying the Apocalyptic Dragon (Royal Museum for Fine Arts of Belgium in Brussels) and the diminutive The Suicide of Saul(Kunsthistorisches Museum, Vienna). The compositional cohesion is greater than before and he makes even more usage of colour accents and rhythmic repetitions. Also on the iconographical level, Bruegel's works becomes yet more diverse.
From the period between 1563 and 1568, until just before his death, there are no less than 29 surviving paintings, amongst which are two versions of The Tower of Babel (1563, Kunsthistorisches Museum; ca. 1568, Museum Boijmans van Beuningen, Rotterdam), The Wedding Banquet and The Village Kermis (ca. 1567, Kunsthistorisches Museum, Vienna) and The Parable of the Blind(1568, Museo Nazionale di Capodimonte, Naples). In 1565, Bruegel paints the series The Twelve Months. Otherwise than in his earlier landscapes, here humans and their actions stand central to the work. Humanity no longer 'disappears' into the meadowlands of the landscape, but is on the contrary, a determining factor for the imagery. What also stands out is Bruegel's economic usage of pictorial means, by which he lets the undercoat show through, for example. The Twelve Months are characterised by a tonal, muted colour palette, which ensures for unity. Bruegel is an adept at capturing the atmosphere of a season: the light, the temperature, the character. In his entire oeuvre, moreover, a special affinity for nature grabs the attention. Between 1563 and 1568, Bruegel's technique becomes even more fluid and loose, with even more earth tones and silver-grey tints. His figures become bigger still, which people generally indicate as being an influence of the Italian Renaissance, and he brings his perspective point lower. Where previously the viewer looked from a higher vantage point and thus from a distance onto the people and landscape, Bruegel makes him now a participant of the scene in this periods. Examples of this are The Sermon of Saint John the Baptist(1566, Szépmüvészeti Múzeum, Budapest) and The Peasant and the Birdnester (1568, Kunsthistorisches Museum, Vienna).