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The most technically difficult opera arias are not always the most profound in meaning, but in Leonore’s solo from the first act of Fidelio the vocal hurdles closely mirror the moral and psychological challenges of Beethoven’s heroine. This essay offers unprecedented in-depth analysis of six audio recordings and four video recordings of this scene, covering a ninety-nine-year timespan. These ten portraits in sound reveal how some of the most talented singers of their respective eras measured up to the challenges of one of the greatest of all operatic scores, achieving a highly individual expressive merging of words, music, and—in some cases—gesture.