Though Mahler usually balked at declaring himself a modernist composer, on occasion he definitively aligned himself with the Austro-German early modernist cohort, who consciously sought out uncharted musical territory between 1890 and 1910. This movement was by no means monolithic; historicist and ironizing trends, for example, evolved side by side with the antecedents of the New Music. This chapter examines modernist traits of the Second, Fourth, and Seventh Symphonies, along with Das Lied von der Erde, as examples of four distinct modernisms: realism, conveyed by operatically conceived offstage sounds; incipient neoclassicism, with transparent Mozartian orchestration deployed in a playful ironic tone; a rare Mahlerian embrace of discordant instability, juxtaposed with a nostalgia that does not quite soothe; and a sui generis case, the emancipation of musical time, which would become emblematic of Mahler’s late style.