This study examines the history of European painting through the lens of Hans-Georg Gadamer’s notion of play,focusing on selected works by Carlo Crivelli and Cornelis Gijsbrechts.It emphasizes illusionistic skills and trompe-l’œil techniques as the foundation for the participatory dimension of play in Gadamer’s hermeneutics. The research adopts a descriptive–analytical and comparative approach,applying this method to thirteen selected paintings by the two artists. It seeks to answer the following questions:How can illusionistic skills and trompe-l’œil techniques in the chosen works be analyzed to expand Gadamer’s concept of play? How might emphasis on visual deception in painting extend the notion of play so that the viewer engages more actively in the interpretive process? The findings indicate that in these works, attention to illusionistic skills and trompe-l’œil techniques is directly tied to Gadamer’s discussion of play. Moreover, the forms of play extracted from each artist’s oeuvre are distinctive. Crivelli’s paintings play with shadows, play with time, play with hidden identity, and play with ambiguity.Gijsbrechts’s works, by contrast, involve play with form and content, play with appearance and reality, play with shadows, play with creation and destruction, play with front and back of the canvas, and play with frame and background. The more visual deception is employed in an artist’s work, the more complex and layered the interpretive play becomes.While early Renaissance painters relied heavily on illusionistic skills, trompe-l’œil techniques became more intricate in the Baroque period. Gijsbrechts’s paintings display a greater number and complexity of plays than those of Crivelli. By identifying levels of meaning and clarifying the formal and internal relations within the works, as well as analyzing the illusionistic skills and trompe-l’œil techniques employed, one can speak of deeper viewer participation. The greater the use of visual deception, the more complex the level of meaning and engagement of the viewer becomes.