In his early career he was a member of the rock group Th' Dudes and was the main creative force in pop band DD Smash.

While Sacred Heart actively encouraged music, Dobbyn was too shy to be involved, and on graduating high school worked nine months as a bank teller, and applied to teachers' college twice, to be accepted on the second try.

[1] Dobbyn suffered extreme stage fright and played early performances standing at the back with his eyes closed.

The band's first release was the single "Lipstick Power", followed by "Bull by the Horns" (1981), thought to be about Dobbyn overcoming the stage fright he sometimes experienced while performing with Th' Dudes.

After Cool Bananas, DD Smash released Deep in the Heart of Taxes (1983), an album recorded live at Auckland's popular eighties venue Mainstreet.

Prime Minister David Lange called a commission of inquiry and as a result, Dobbyn was charged with inciting a riot.

His lawyer successfully defended him and he was acquitted on the charge of "behaving in a manner likely to cause violence against person or property and using insulting language".

[6] When DD Smash eventually disbanded, partially to make room for the commercially expanding vision of Dobbyn, they left behind them the hit singles "Outlook for Thursday" (1983) and the violin-tinged, hi perennial classic "Whaling" (1984).

When DD Smash folded, Dobbyn began a successful solo career, by writing the soundtrack music for the animated feature film Footrot Flats: The Dog's Tale in 1986.

The film yielded two hit singles: "You Oughta Be In Love" (1986) and the chart-topping "Slice of Heaven" (1986) recorded with the band Herbs.

After the release of the film, "Slice of Heaven" became one of Dobbyn's best-known songs, frequently used in tourism advertisements aired on Australian television that encouraged people to visit New Zealand.

In April 1987, a re-worked version of Dobbyn's song "Slice of Heaven" featured in a number of television commercials in Australia.

In 1999 Dobbyn joined Jan Hellriegel and Toi Iti to co-write "Read About It", the theme song of the Duffy Books in Homes programme[12] which is still performed by 100,000 children annually.

During the performance, Ahmed Zaoui, who was appealing a security certificate issued due to alleged links to terrorist groups, appeared on stage with Dobbyn.

In 2009 Dobbyn released a second greatest hits album, including re-recorded versions of "Devil You Know", "Shaky Isles" and "Whaling".

The award presenter Michael Glading, the managing director of Sony New Zealand, chose to forego a speech and instead read out the titles of the long list of Dobbyn's hit songs.