It's a sentiment that's become even more apparent as he plays shows in support of his Greatest Hits album.

"It's a little scary, because it does make you feel old," the singer/songwriter said of fans relating stories to him.

"A lot of people come up and say, 'that song you played, we played that at our wedding'. Or 'we lined up this song of yours at my Dad's funeral, because he loved that song'.

"That's one end of the spectrum to the other. Life and death, and if your music actually figures in people's lives, I think you're going okay."

Cassar-Daley, who turns 50 this weekend, released his Greatest Hits double-CD set in October 2018.

Cassar-Daley has achieved 31 No.1 chart singles, all of which are collected on the compilation record, alongside album tracks and two brand new originals.

Throughout 30 years of making music, he's been awarded numerous accolades including ARIAs, Golden Guitars and APRA Country Song of the Year awards.

"What people get is myself, sitting on an acoustic guitar, giving people exactly what they expect I believe," he said of his current tour.

"It's really familiar. It's pretty much how the songs were born, how I'm presenting them. And in an acoustic format like this, it's very intimate."

The opening act on Cassar-Daley's Greatest Hits jaunt is his 18-year-old daughter Jem, who is performing professionally for the first time on this tour.

"She finished school last year and was going to take a gap year," he said.

"I played the devil's advocate and just said, 'how about you come out and be a bum muso for 12 months with Dad, and open some shows?'"

A self-professed "proud Dad", Cassar-Daley said it had been exciting to watch his child grow as a performer and person.

"She's always sung at home, and won a lot of eisteddfods at school, but never really shared it with anyone outside of our own environment at home.

"She's been on the road since February, and she's winning hearts all over the place, and loving every minute of it. It's been great."

Although uncertain if this will lead to Jem pursuing music full-time, Cassar-Daley said she was already receiving gig booking offers in her own right.

"It makes me proud that I'm not pushing her on to people; people hear her sing and they say, 'we should book her'," he laughed.

-Troy Cassar-Daley will perform at Anita's Theatre on Friday, June 14.

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