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Longest Roman Numeral

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A key shows Roman letter values: I = 1, V = 5, X = 10, L = 50, C = 100, D = 500, M = 1000. Examples: 27 = XXVII (5 letters) and 64 = LXIV (4 letters). Using the standard form (9 is IX, never VIIII), which number from 1 to 99 has the longest Roman numeral?

Which number from 1 to 99 has the longest Roman numeral, written the usual way?

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