Potential answers for ""American Boy" singer"

⭐⭐⭐⭐ ESTELLE
⭐⭐⭐ KANYEWEST
⭐⭐ BUDDYHOLLY
⭐⭐ BETTEMIDLER
⭐⭐ JOHNNYCASH
⭐⭐ YENTL

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It's worn with a sporran   "My plans have gone ___"   It's indicated by an IOU