Ray Woolf's journey in the entertainment industry began when he was just 13 years old, singing in rock bands in his native Dagenham, Essex. After moving to New Zealand in 1962 at the age of 17, he started performing at Auckland dance halls and was soon signed to Zodiac Records, commencing his recording career.
Throughout the 1970s, Woolf featured on a variety of popular shows, including In the Groove, On the Beat Side, C'Mon, and Happen Inn. He later hosted his own chat show, The Ray Woolf Show, which boasted a live band and audience.
In addition to his music career, Woolf also presented the New Zealand children's program Playschool for 18 months, embracing the philosophy of seizing every opportunity that came his way. This role provided Woolf with greater creative freedom compared to the structured pop shows he was accustomed to.
One of Woolf's most notable acting roles was as the helmsman of the steamship Venture in Peter Jackson's King Kong (2005),released in 2005. Although his screen time was brief, he enjoyed the experience due to the pleasant company he encountered on set.
A member of the New Zealand Order of Merit for his services to entertainment, Woolf has also appeared in productions such as The Sound of Music (2004),West Side Story, and The New Rocky Horror Show. He has collaborated with various musicians over the years and continues to perform with the Rodger Fox Big Band.
Although Woolf is now retired and receiving a pension, he remains committed to his passion for entertainment and is determined to continue performing, despite the regular government payments he receives.