The veteran entertainer is bringing his show to Armidale later this month.

“I thought it was time to show how these songs were born, because you can’t really show that side of a tune without doing it acoustically,” Cassar-Daley said.

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“Say I’ve sat down with Col Buchanan and written a song, when we first play it acoustically together the song has a bit of an essence to it that never, ever gets kept. It always gets produced and then recorded.

“I wanted to go out on the road and show people how these songs were born, and some of the stories behind them.”

Special guest for the Greatest Hits Acoustic Tour is Jem Cassar-Daley who has been opening the show for her Dad every night. The 18-year-old, a talented singer and pianist, is taking a gap year in 2019.

“Instead of her taking a gap year and costing her money, I think she’s going to save a bit, and maybe pay us back for that half of the car we paid for,” Cassar-Daley said.

“She’s a great little artist and she’s not wanting to go out pursue a country music career, but I wanted her to see the privilege that is playing music for a living, from my perspective I guess and how exciting it is to see Australia the way I do. I wanted her to see it through my eyes.

“What better bonding could you have with one of your kids than that?”

Jem opens each show with a half-hour set.

READ MORE: Young Cassar-Daley breaks free from country music dynasty

Cassar-Daley says the idea to release a greatest hits album came from his wife.

“I don’t know if there was too much wine involved, but she said ‘you’ve got quite a catalogue of stuff, have you ever thought about doing a best of,” Cassar-Daley said.

“I said ‘not really’.”

But then he thought about it. 

While Cassar-Daley has won 37 Golden Guitars since collecting his first one in 1996, and has had 31 singles reach number one, in recent years there have been reasons to reflect on his career.

From releasing a very honest autobiography to being elevated to the Country Music Roll of Renown, the last couple of years have been a time that has recognised Cassar-Daley’s place as one of the all-time great artists in Australian country music.

"I figured that instead of going through a mid-life crisis I might gather up what I’ve done over the last 30 years of playing music and put into some sort of form and have a look at it.

“So I did it, and I thought this is not a bad idea, it’s not just the wine talking.”

The result is a collection of 42 songs, from the very first single he recorded while living in Tamworth in the early 90s, through to his latest single, Wouldn’t Change A Thing.

In between are all 31 songs that reached the top of the chart, with a few others thrown in as well that are often requested by fans.

Cassar-Daley admitted he was not be able to include all 42 tracks that are on the album in the greatest hits show, but he did know which songs would not miss out.

“I normally would never play a set without River Boy, I would never play a set without Born To Survive, or They Don’t Make ‘Em Like That Anymore. I’d have to put in Ladies In My Life, (and) Freedom Ride is a really important song.

“The whole idea of the show is that it’s full of familiarity for people. There will not be one in there that hasn’t charted at number one. It’s all going to be songs people know.”