This drawing can be dated to Schäufelein's years in Augsburg from 1510-1515, a period in which he developed to full maturity as an artist independent of the strong influence of Albrecht Dürer, in whose studio he had worked from circa 1503-1505. This development can be seen, for example, by comparing the smooth, relaxed and elegant handling of the present drawing to the careful, balanced and delicate manner of the clearly Dürer-inspired Lady in elegant dress in the Kupferstichkabinett, Berlin, of circa 1507-9 (From Schongauer to Holbein, Master Drawings from Basel and Berlin, exhib. cat., Washington, National Gallery of Art, 1999, no. 83).
A drawing of a Landsknecht with his head turned to look behind him, of very similar composition although of slightly earlier date, is in the British Museum (J. Rowlands, op. cit., 1993, no. 446). That Landsknecht wears a similarly flamboyant feathered cap, and likewise carries a halberd and a 'hand and a half' sword. Both drawings are close in feeling to Schäufelein's woodcuts of a A German soldier walking to the left and A standard-bearer walking to the right in front of a castle (Hollstein 63-64).
The image of the Landsknecht was very popular in Switzerland and Southern Germany in the early 16th Century for the moral lesson that it presents. The studied elegance, even arrogance, of the figure is neatly contrasted with his unspoken but clearly implied venal brutality as a mercenary who would have taken part on both sides of the vicious wars fought across Northern Italy and Central Europe in the period. Landsknecht regiments were first formed by the Emperor Maximilian I (1459-1519) with recruits from Swabia, Alsace, Flanders and the Rhineland, and were intended as a more flexible alternative to the rigid formations of the Swiss mercenaries in the face of new military technology. They first saw action in the Italian Wars of 1494-1559, repeatedly changing sides in the struggles between the Papacy, the Italian States, the French and the Holy Roman Empire. Their reputation for brutality was cemented by service for the French in the bloodthirsty defeat of Swiss forces fighting for the Duchy of Milan at Marignano in 1515. It was actions such as this, at which the Swiss artist Urs Graf was present, that led to the Landesnecht becoming such a potent symbol in Swiss and South German art. Schäufelein's particular association with the subject may be related to his many woodcuts on subjects related to the Emperor Maximilian published in this period.
A Portait of a man, bust-length, wearing a hat by Schäufelein was sold at Christie's, New York, 23 January 2002, lot 131.