In 1961, jazz pianist Ronnie Smith set up a group to play at the Sorrento Club, Wellington.

[2][3] Smith's group had Tommy Tamati on bass guitar, and May joined on drums and backing vocals.

[3] Bruno Lawrence, an English-born jazz musician who was regularly in the audience, often got up to play the drums when May sang lead.

[3] At the end of 1961, May returned to Auckland and signed with Harry M. Miller's La Gloria label, which released his debut single in 1961, a cover version of the Chubby Checker hit "Let's Twist Again".

[4][5] From March of that year, he hosted the Sydney teen pop music TV series Ten on the Town on TEN-10.

In 1974, ABC decided to release a second double album, Just Foolin' Around – A Tribute to Louis Armstrong.

[9] On 1 June 1988, Ricky May had a fatal heart attack at the Regent Hotel, Sydney, after getting a standing ovation on the opening night of a new cabaret show.