This article looks at the history of jesters affiliated with the Iranian court during the Safavid and Zand periods. I present several case studies of jesters (dalqak), featuring Kal ʿEnāyat and Dalāleh Qezī from the Safavid period and Lūṭī Ṣāleḥ from the Zand period. From various primary resources including memoirs, European travelogues, and court-associated chronicles, I relate several accounts associated with these personalities and describe their unique relationship with the ruling shāh of their time. Through various staged and spontaneous performances involving irony, subterfuge, and satire, jesters – as embodied “mirrors for princes” – demonstrate the inherent precarity of the shāh's rule and the need to be accountable to his subjects. In comparing the Safavid jester to others across time and place, the performative simulation of transcending the status quo's gender, class, political, and moralistic boundaries will be shown to help preserve them.