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The Mosgiel 12-year-old won the junior category at the Gold Guitar Awards in Gore last weekend.
It was "quite cool" to be on stage in front of a 900-strong crowd, even though he was "a little bit nervous", Caleb said.
Caleb's covers of There's a Hero, by Billy Gilman, and Arms of Jesus, by Julie Roberts, won him the junior overall and junior vocal solo titles, which came with two trophies and a guitar.
He was happy to have won the category this year, after being a finalist last year, his first time at the awards, Caleb said.
The Taieri College pupil said his first performance on stage was as an 8-year-old in a talent show at primary school, so he was getting quite comfortable on stage now.
Music was also becoming a larger part of his life - he started piano lessons at the beginning of the year and tomorrow will begin guitar lessons.
The Elton John fan said he had been taking singing lessons from vocal coach Bridget Telfer since 2016.
But his talent may be genetic - his grandfather Bill Croy sang with the New Zealand Opera years ago, and his father Quentin Croy was also a singer.
His dad said he was amazed by Caleb's talent, and looked forward to watching his son's progress.
"This is only the start of many years to come."
-By Fisi-Belle Carrasco-Rex