General Comments

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(I'd like to note that "manly timbre", talking about tenor, while it's technically a register for male singing, I don't think it's necessarily thought of as masculine. So I'd daresay that this is ironic at passing glance.) I think it's the point Walt is trying to make, by punning "deepest of all to me the lesson" it's not the actual voice that clicks for him, but what is sung, with what emotion the singer puts into it.
Note from the Walt Whitman Archive, on a letter from TJ Whitman to Walt: 1. Walt Whitman readily acknowledged his admiration for Italian opera and stressed its importance to his poetry, even claiming that the method of "A Child's Reminiscence" (1859; later "Out of the Cradle Endlessly Rocking") was "strictly that of the Italian Opera" (Robert D. Faner, Walt Whitman & Opera [Carbondale: Southern Illinois Univ. Press, 1951], p. v). Late in his career he again emphasized this influence in "The Dead Tenor" (1884), a memorial tribute to Pasquale Brignoli: "How much from thee! the revelation of the singing voice from thee!/ ...How through those strains distill'd—how the rapt ears, the soul of me, absorbing / Fernando's heart, Manrico's passionate call, Ernani's , sweet Gennaro's ." Jeff and Walt often attended operas together, especially during the period 1854-62. After the poet left Brooklyn for Washington, Jeff continued, in spite of the war conditions and a shortage of funds, to attend the opera "quite often" on his own. He and Walt shared similar tastes, as those composers, operas, and performers that Jeff mentions—Verdi's Il Trovatore , Donizetti's La Favorita , and the singers Amodio, Francesco Mazzoleni, and Josephine Medori—were ones that Walt praised in essays, notebook jottings, and letters. As Jeff's appreciation for the opera grew, he instructed his former teacher by guiding Walt to the latest arrivals on the New York stage and encouraging him to hear them.