In 1575 Friedrich Sustris decorated Trausnitz Castle in Landshut with paintings proclaiming the political and religious aspirations of Duke Wilhelm V of Bavaria. The duke’s staunch support of the Counter-Reformation and politically advantageous marital alliance with Lorraine are visually reinforced in the castle’s ceremonial rooms. In contrast, a narrow stairwell in the private ducal quarters surrounds the viewer with an illusionistic performance of the commedia dell’arte. The burlesque sexual antics of the commedia had entertained the guests at Wilhelm’s wedding to Renate of Lorraine in 1568. Past interpretations of the “Stairway of Fools” have tied it to specific performances, requiring that the figures be treated as a linear narrative. This article will demonstrate how the pictorial rendering and the architectural confines of the stairwell not only reflect the improvisational nature of the commedia dell’arte, but relate equally to the political iconography of the castle by recalling the wedding of Wilhelm and Renate.