Mr Bennett (78), a retired chartered accountant, was just 24 when first elected as a councillor in 1956. He became mayor in 1971 for a year, when the incumbent, Durham Dowell, retired to Christchurch, and he took over for the rest of the term.
Then it was back to being a councillor until he successfully contested the mayoralty in 1977 and again in 1980.
He retired from the mayoralty when he became general manager of The Timaru Herald, so had a break from council duties for four years, before being elected back on to council in 1986 and then 1989, following the reorganisation of local government, and he has been there ever since.
Mr Bennett always wanted to be a councillor - his grandfather Joseph Shepherd Bennett was a councillor in Timaru from 1885 until 1899 - and he kept standing because of a desire to help people.
"The only reason I'm here is to help people and try and interpret what people want. The only reason you've got a mayor and councillors is you can't get 42,000 people in the council chambers.
"You've got to try and interpret what people want and what they can afford."
To be a good councillor, it took courage, along with sticking up for your ideals and for what you believed was right.
"I don't agree with grand-standing or trying to push your own barrow. I've never done that and never will."
While he had been very lucky to achieve a record number of terms, he said he never attempted to set a record.
Mr Bennett enjoyed his stints as mayor - which he described as "absolutely the cat's whiskers" - and a highlight for the self-confessed royalist was showing Prince Charles around Caroline Bay in 1977.
He also enjoyed the team spirit on the council.
"You've got to like what you do. If you didn't like it, it would be no good standing for council and getting in. You've got to enjoy it."
Describing himself as "Timaru to the back teeth", Mr Bennett was also involved with numerous groups and organisations in the community.
"I'm doing as much now as I was doing 50 years ago and loving it. I'm not slowing down, hell no."
"I still think young. Age doesn't worry me, I keep going."
And, what if he doesn't get re-elected this time?
Well, if voters thought other candidates were better suited to the present climate, then he would accept their decision, but he would always be grateful to those who had supported him for so many years.
