Potential answers for ""__ Day": Holly hit "

⭐⭐⭐⭐ EVERY
⭐⭐ WEEZER
⭐⭐ DESERTROSE
⭐⭐ PEGGYSUE
⭐⭐ SECADA
⭐⭐ MAYBEBABY
⭐⭐ OLDIE
⭐⭐ THATLL
⭐⭐ OHBOY
⭐⭐ FEELIN

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Brands, maybe    "The Merry Widow," e.g.    Like many bad decisions