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This essay examines a creative dialogue between painters and poets, among them Nissim Ezekiel, Adil Jussawalla, Bhupen Khakhar, Arun Kolatkar, Arvind Krishna Mehrotra, Gieve Patel, and Sudhir Patwardhan, in Bombay (Mumbai) during a period that encompassed Khakhar’s first solo show at the Jehangir Art Gallery in 1965 and the publication of four books of poetry by Clearing House, an independent press established in 1976 by Jussawalla, Kolatkar, Mehrotra, and Patel. Through a close analysis of word and image, it illuminates the distinctive aesthetics and politics of these artists encapsulated by the terms lifting and loafing. The Bombay painters and poets came to lifting—documenting and defamiliarizing—their environment by citing and subverting street signs, advertisements, state propaganda, calendar art, film posters, and newspaper photographs. They took to loafing—a mode of critical observation and analysis, and the pursuit of committed deprofessionalization and translation across spaces—and mobilized the ordinary, yet extraordinary, spaces of the paan (areca nut wrapped in betel leaf) shop and the Irani restaurant as metaphors of artistic sociability and subjectivity. Through lifting and loafing, the Bombay painters and poets offered a critique of nationalist and bourgeois values, as well as the artistic establishment represented by associations and institutions such as the Progressive Artists Group and Jamsetjee Jeejebhoy School of Art. They diverged from their predecessors and peers in an emphasis on everyday life and found objects, and in bringing together the visual and verbal worlds exemplified by the Baroda (Vadodara)-based journal Vrishchik.