This article analyzes the literary legacy of Ubaydi (Ubaydullah Khan), a sixteenth-century poet-ruler and a representative of Uzbek classical literature. The study examines his worldview shaped by complex historical and political conditions, his poetic interpretation of kingship and poverty, the originality of his love lyrics, his multilingual literary heritage, and his religious and educational activities. Special attention is paid to Ubaydi’s pursuit of spiritual perfection and his inclination toward simplicity and folk-oriented expression as defining features of his poetry.