As rector Clive Rennie welcomed seven former pupils, all aged between 92 and 97 and who started at the school in the late 1920s, to the two-day reunion, he pointed out he was also taught by three of their teachers when he attended the school in the late 1950s and early 1960s.
When asked why five of the men were chartered accountants, now retired, Angus MacIvor (92) said an economic downturn, which made the current international financial crisis pale by comparison, played a large part in vocational choices.
"You have to understand the times. It was the last years of the Depression and you just couldn't get jobs. There were 18- and 19-year-old blokes in my form whose parents had sent them back to school because there were no jobs. But, to matriculated boys, an education was like an insurance policy."
Many pupils would attend evening classes in accountancy and book-keeping at the University of Otago's department of commerce.
"Although there was no great scholastic ability required, we had to work very hard at it. I saw poverty then I never want to see again."
Mr MacIvor later moved to Auckland and established an accountancy firm.
Sydney resident Donald Munro said he generally enjoyed his time at the school but preferred physical education to academic pursuits.
The 96-year-old found much of the school unrecognisable but was pleased the 19th century "character" buildings had been retained.
After leaving New Zealand, Mr Munro studied at the Royal College of Music, receiving the Tagore Medal.
On his return to New Zealand, he was instrumental in establishing the country's first opera company (in 1953) and was later dean of the faculty of music at the University of Adelaide.
He has lived in Sydney for more than 40 years.
"No, there was no music here at all, but I enjoyed the physical activities. We were all assembled and marched in everywhere. Discipline was pretty tough and we were caned for any small misdemeanour. But it was also just accepted and we didn't hold it against the teachers at all.
"It was a good education, and many of the teachers were very good, so I would say it stood us in good stead."
Mr Munro, who was born in Mosgiel and grew up in Dunedin, had not visited the school since 1927.
When asked if he was also a retired accountant, the Rev Stewart Anderson (92), of Lower Hutt, said: "Oh no. I was ordained. That was far better."
The two-day reunion, which concludes today, was hosted by the Otago Boys High School Foundation.
Also attending are Bill Isaac (97) and Percy Wellington (97), of Dunedin, Rodney Eastgate (92), of Christchurch, and John Manning (94), of Lower Hutt.
