The article addresses a problem of mediation through the lens of imagination. An idea of “intermedial imagination”—a critical faculty that bears witness to the world’s out–of–jointness” — proposed by Pietro Montani is analysed and brought in the context of Bernard Stiegler’, Gilles Deleuze’s and Jacques Derrida’s thinking. In this way, imagination is associated with various functions of montage, rather than synthesis, as well as revealed as the power of overcomingclichéd forms and fetishes through its shape–shifting and unprecedented transformations. The article also offers an analyses of exhibitions by Raimundas Malašauskas (Photo Finish in Vilnius, and the Lithuania/Cyprus “oO/Oo” Pavilion at the 55th Venice Biennale) and the avant–garde performances of Romeo Castellucci.