Toogood was born in Wellington and lived there until 1952 when he moved to Heretaunga in the Hutt Valley. After an inauspicious start at school, he became involved in theatre and radio, including a role in New Zealand's first radio soap opera.
In 1939, he joined the army and, promoted to the rank of major, spent time in Italy and North Africa as a supply officer. It was on a troopship on the way home that he ran his first quiz show. After the war, Toogood picked up where he'd left off as a stage actor, voice-over artist and radio announcer.
He began his career as a radio host in 1946 and was the originator of the game show It's in the Bag, in which he popularised the catch-phrases, "By hokey", and "What will it be, customers - the money or the bag?", in New Zealand. It's in the Bag eventually moved on to network television, where it was equally successful. He published his autobiography Out Of The Bag in 1979. Toogood hosted numerous other TV shows for the Broadcasting Corporation of New Zealand and Television New Zealand, including the panel show Beauty and the Beast and the children's quiz show W3. He retired from It's in the Bag in the 1980s, handing over the mantle to radio and TV host John Hawkesby.
In the 1977 New Year Honours Toogood was appointed a Companion of the Queen's Service Order for community services. Toogood was awarded a special lifetime achievement award by the New Zealand Academy of Film and Television Arts in New Zealand in 1999.