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Stanley Cavell's critical-aesthetic way of doing philosophy charts a unique path between dogmatic doctrinalism and dull despair in response to the alienations that trouble modern divided life. His methods of attention to cultural phenomena are rooted in a philosophical anthropology that sees human subjects as forever fated to live between complete reconciliation and individualist-instrumentalist transactionalism. Some works of literature, music, and film, he finds, arrest and absorb their audiences in the fullness of their registerings of this continuing condition and in somehow making meaning and achieving dramatic, non-doctrinal closure. They model for these audiences how temporally situated and finite moments of meaning-making are possible. In doing so, they show us how we might live within our shared condition more productively through engagement with the affordances of art. Cavell's own writing in turn both describes and re-enacts this achievement, thus itself manifesting the powers of art in response to modern life and serving as a model of 'knowing how to go on' within its ambit. These essays describe and defend Cavell's philosophical anthropology and critical-aesthetic practice. Anticipations of Freedom situates that practice as both a response to and a furthering of an image of America as a site of futural freedom always to be achieved, and it extends Cavell's practice into new readings of works of poetry, film, and music.