This essay reviews and discusses a panel of papers on the topic of transgender. The five papers under discussion—theoretical, clinical, and an interview—constitute a paradigm changing view of transgender identifications and indeed gender identity more generally. The discussion focuses on thinking about transgender phenomena in cultural context, as a spectrum of positions and modes of being, as presenting issues of development, and as deep instances of psychic pain and psychic exhilaration. The interface of cultural theory and psychoanalytic theory is considered. Transgender experiences in analyst or analysand will entail rethinking questions of embodiment, of social construction, of trauma, and of family transmissions of meaning. Implications for psychoanalytic thinking and work about identity and sexuality, developed in all the papers in this fascinating panel, are considered.