He started making musical appearances, doing cover songs, on New Zealand television screens.
It was the infancy of television in New Zealand but Woolf, who fronted Ray Woolf and the Avengers, quickly became well-known throughout the country with his music as well as appearances on shows such as C'mon and Happen Inn.
He was well remembered as a host of Play School and a particular highlight was fronting the light entertainment chat show called The Ray Woolf Show.
"He was actually the last one to really have a live entertainment show where he would interview people, some of them would sing, he would sing," Roger said.
Woolf, who lives in Northland, and is still performing, enjoyed helping create the book.
"I relived a whole lot of stuff I had forgotten about.
"It's not until you start digging and thinking about things that stuff sort of comes back.
"It was an amazing experience and good to reflect on."
He had read the book a few times and spoken to a few people to get feedback.
"I really like it.
"It talks about a lot of things and kind of deals with quite a historic time in New Zealand.
"I came to New Zealand in 1962 — there were no mobile phones, not much television, no computers, no media stuff, it was a totally different world.
"The whole thing was just getting into gear in terms of rock and pop music."