A musical direction meaning to perform with the utmost sorrow, melancholy, or deepest mournful expression; the superlative form of dolente.
From Italian dolentissimo, superlative of dolente (sorrowful). The -issimo suffix in Italian indicates the superlative degree, standard in musical notation since the Baroque era.
The -issimo suffix is Italian's way of saying 'extremely'—so 'dolentissimo' is grief turned up to eleven, and composers use it when regular sadness just won't cut it, like in the final movements of Romantic requiems.
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