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

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

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Occasions for outdoor smoking, briefly?   Brewing beer or collecting coins, e.g.   Win, and then some