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How is lamentoso played?
The composer writes lamentoso (also lamentando, lamentabile) to ask the performer to play in the manner of a lament — weeping, plaintive, grief-stricken. It is an affect direction rather than a tempo, and it points toward a deep tradition in Western music in which grief is set as a 'lament': descending melodic lines, sighing two-note slurs, and the descending 'lament bass' or chromatic tetrachord. Performers respond with expressive rubato, drooping phrase-ends, and an emphasis on the falling shapes that signal sorrow.
How does lamentoso sound?
A weeping, plaintive sound that imitates the gestures of crying and mourning.
In context
The Wikipedia glossary defines lamentoso (and lamentando) as 'lamenting, mournfully'. The marking invokes the Baroque lament tradition built on a descending bass, exemplified by Purcell's 'Dido's Lament' and Monteverdi's 'Lamento della Ninfa', though lamentoso is itself a general expressive direction rather than a single attributed work.