Before canvassing those years we'll begin in the present. Roy's only been "one of us" a little over a year, arriving in the wake of the Christchurch earthquakes.
A Rotorua-based daughter enticed him to leave his historic Sumner home when the cliffs above it were left teetering. It took considerable persuasion to shift him - "I didn't want to be a refugee".
Nor was he impressed living with Rotorua's pollen count. Visiting after the first quake he suffered such bad hay fever his voice vanished for several weeks.
"A bloody nuisance, everyone still wanted me to sing."
He's been a rest home entertainer since his late wife moved into one years ago now. An impromptu performance startled us out of our chair, his voice retains the strength of an opera pro.
When Roy was 3 his father died, a victim of the 1918 Spanish influenza pandemic. His first memory dates to the same year: "Seeing a Maori warrior doing the haka in Palmerston North for the Armistice".
Roy's mother's heart had been set on him learning Latin and becoming a missionary.
"When I was 14 I sold the books, I told her the Depression was on and she couldn't afford to keep me at school, she burst out crying."
He found work in a furniture shop; it was a stop-gap measure. At 15, he joined the post office but nearly didn't make the grade.
"They said my writing wasn't of the required standard, my mother had beautiful writing, she taught me so well I now write as neatly as a machine."
Passing muster, the young Roy was funnelled into the telegraph branch, learning to transmit and decipher Morse code was a must. It's an ability that's taken him to the edge of international espionage.
"I was working in Hawke's Bay, another boarder billeted with me offered to drive me around the countryside saying he was measuring hills and trees, I thought it funny then one day I heard German voices in the shower, I told the boss. Later when I was in the desert [during World War II] this girl I'd been seeing sent me a news clipping saying that man had been arrested as a German spy."
Nor was it a one-off encounter with the foe. When a Porangahau farmer spotted lights flashing out at sea Roy was sent to interpret.
"I couldn't see anything being transmitted in Morse but I could hear foreign voices."
The outcome: an urgent telegram summoned him to defence HQ in Wellington.
"I was recruited into the army and told if I didn't obey orders or made any serious mistakes I'd be shot on the spot."
Introduced to his first commanding officer he did a double take.
"I'd worked with him in the Waitotara Post Office . . . had kissed his daughter in the broom cupboard."
Posted to Egypt his Kippenberger connection began.
"Then I was the only one in the regiment who could read Morse."
As signalmen in Greece he and former post office colleague, Arthur Helm, were equipped with a van.
"It made us far more visible to the Germans than the infantry, when we were coming under attack we'd have to bury and camouflage it then dig it up again ... oh, how my arms ached."
As a signals runner in Crete, Roy found himself stuck behind enemy lines "until this British officer swooped in, whisking me out on a motor bike".
War stories of this ilk would fill volumes. When hostilities ended Roy returned to the post office, marrying the girl who'd sent him the news of the spy's arrest.
Based in Hunterville he had a run-in with authority - for forging his boss' signature on cheques. He cheerfully pleads guilty.
"I did dozens of them, he was a raging alcoholic, out in the street at 6am screaming his head off, too drunk to sign anything so I signed them in his name."
As punishment he was sent to Carterton.
"The postmaster didn't want to know me but my singing saved me because he needed someone for his church choir."
Around this time Roy became immersed in fundraising for Ed Hillary's tractor expedition to the South Pole, spurred on by his old mate Arthur Helm, then Scott Base's postmaster.
He treasures a copy of a letter Hillary wrote en route. The explorer's description of his huskies sleeping in the snow makes tender reading.
After years yo-yoing around New Zealand, Roy's postmaster career came to a close in Sumner in 1970. Time with the late cricket great Sir Walter Hadlee's accountancy firm followed.
Naturally we're compelled to ask if he's counting on scoring his own century?
"Nah, I'm not bothered about it."
