Was it as early as 1979 when as a weedy pub-rocker he punched above his weight in Th' Dudes, forever engraving Be Mine Tonight on our collective subconscious? Was it as recently as 2006 when he performed uber-hymn Welcome Home before the Royal Family at the dedication of the New Zealand War Memorial in Hyde Park, London?
More likely it was somewhere along the way, the point at which his voice became that of an approachable, eloquent Kiwi joker as opposed to rock-band frontman or guitar-slinger.
And while pop hits such as Outlook For Thursday, Oughta Be In Love and Slice Of Heaven had set middle New Zealand's toes tapping and had clocked up plenty of airplay, richer rewards emerged from songs that didn't beg such attention.
The Islander (1998) is the kind of album that singer-songwriters love to make. Free from the hall-of-mirrors effect that hit singles inevitably have on the shape of things, it stands as a consistently fine collection of songs, loosely bound by notions of identity.
Dobbyn said on the album's release that he had long considered himself a Pacific Islander, keenly aware of New Zealand's unique place in the world, distant from any meaningful European ties.
Songs such as Mobile Home, Hanging In The Wire, Be Set Free and Keep A Light On bear out this sense of independence without tying it to nationhood, instead imparting the flavour of our way of life by speaking of resoluteness, freedom and compassion.
Waiting speaks of a less laudable Kiwi quality, impatience. Delivered with a hint of a DD Smash-era snarl, it serves to balance the soul-stirring Beside You and love songs such as What Have I Fallen For.
Perhaps this is the point at which we handed Dobbyn the keys to our cities. He'd told the world about us without making a fool of himself.
