Challenger was part of Wollongong bands of the 1980s, Engineer Brains and The Start, and 1990s outfit The Merry Widows.

In that time, he’d written a few tunes and – with technology making things so easy – decided to record them all and post them up on Soundcloud.

‘‘The original idea was to get down all the songs I had already written,’’ Challenger says.

‘‘That was about 10 of the 14 songs. The oldest one that made the cut is Never Would Be Too Soon, which I think might have been the first song I ever wrote, back in 1985.

‘‘During the process, it stirred the creative juices and in between recording the older songs, every now and then I’d be sitting down with a guitar strumming a few chords and thinking ‘that sounds good’.

It was the catalyst to going ahead and writing some new material.

‘‘Even though I didn’t think they’d ever be played live at the time I thought, given that these ideas are there I’ll just go through and record them as well.’’

And that’s where it was supposed to end – partially because recording and posting them online is an easier way to get people to hear your songs than getting a band together and the hassles of finding time to rehearse.

But then Challenger tapped former Merry Widows bandmate Johnno Beniuk to help with some of the mixing.

‘‘I got the last song out about a few months ago and then Johnno said ‘Hey, what do you think about playing these songs live?

We should play these songs live at least once’,’’ Challenger says.

‘‘It really started from that idea. I thought it was great because I didn’t think I’d ever play live in a band again.’’

Getting that band together turned out to be pretty easy. Three-quarters of the Merry Widows – Challenger, Beniuk and Beniuk’s brother David – signed up for The Insiders.

The rest of the band features drummer David Crowe, keyboard player Marco Forlano and bassist Malcolm Wales from Mustard, who supported the Merry Widows at a few gigs back in the 1990s.

There’s another link to the Merry Widows in that the show is a fund-raiser for the band’s former roadie Kevin English who has Huntington’s disease.

The Insiders and support acts Stephen Robinson and Patrick Lyons and the American Creek Band will be donating their fee for the evening – a percentage of the bar – to English.

Another reason to turn up is this is probably going to be The Insiders’ only gig – at least for a long while.

‘‘I think so,’’ agrees Challenger.

‘‘It’s likely to be a one-off, but we’ll see how it goes. I wouldn’t say no to something again a year later, but we certainly won’t be doing three or four gigs in the next few months.’’