Potential answers for ""5 O'Clock" singer"

⭐⭐⭐⭐ TPAIN
⭐⭐ PAIN
⭐⭐ HALEY
⭐⭐ BILLHALEY
⭐ MADONNA
⭐ COMO
⭐ ADAMS
⭐ DST
⭐ WISE

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16, for 32   Mass, e.g., in Boston   Deliver a dull speech to, say