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Sonnet 99 is generally grouped with the two preceding sonnets, with which it shares a dominant trope and image set: the beloved is described in terms of, and judged superior to, nature and its beauties.

I criticized the violet, telling it that it had stolen its sweet smell from my beloved's breath, and its purple color from my beloved's veins. I told the lily it had stolen the whiteness of your (that is, the beloved's) hands, and marjoram had stolen the beloved's hair; a third flower had stolen from both; in fact, all flowers had stolen something from the person of the beloved.

Edward Massey and others asserted that the poem was directly inspired by a poem in Henry Constable's Diana (1592); T. W. Baldwin rejected this claim while noting that the same Constable sonnet had inspired a passage in The Rape of Lucrece. At any rate, the conceit is common, and parallels have been found in the poems by Edmund Spenser, Thomas Campion, and others. George Wilson praised the poem as an example of synesthesia.

The sonnet has attracted some attention as one of those which appears to provide clues about the historical identity of Shakespeare's subject (on the traditional assumption that the poems are in some sense autobiographical). In 1904, C. C. Stopes noted the existence of a portrait of Southampton at Welbeck Abbey in which his hair curls in a manner similar to young marjoram. This analysis has been disputed by scholars who assert that smell, rather than appearance, is the primary referent of Shakespeare's line. Because of the extravagant praise of the beloved's body, some Victorian scholars were reluctant to believe that the poem was addressed to a man; current consensus, however, groups it with the other poems written to the young man.

The sonnet has 15 lines, and is the only poem in the sequence with more than fourteen (126 has 12). Sonnet structure was not fixed during the period, and Sidney Lee adduces many examples of fifteen line sonnets. An extra line is particularly common in linked sonnets, and this sonnet is linked to 98; Malone ended 98 with a colon to demonstrate the connection. However, other scholars have remarked on the clumsiness of the first line and suggested that the quarto text represents an unrevised draft that found its way into print.

• Alden, Raymond. The Sonnets of Shakespeare with Variorum Readings and Commentary. Boston: Houghton Mifflin, 1916.
• Baldwin, T. W. On the Literary Genetics of Shakespeare's Sonnets. Urbana: University of Illinois, 1950.
• Lee, Sidney. Elizabethan Sonnets. Westminster: Constable, 1904.
• Stopes, C. C. Shakespeare's Sonnets. London: Alexander Morig, 1904.
• Wilson, George. The Five Gateways of Knowledge. Cambridge: Macmillan, 1856.