Field attended Macquarie University to receive training in early childhood education, and founded the Wiggles with fellow students Murray Cook, Greg Page and former bandmate Jeff Fatt in 1991.

His great-great aunt was Queenie Paul, known for performing at the Tivoli Theatre in Sydney, and his grandmother Kathleen accompanied silent movies in the mining town of Cobar.

[3] He attended the all-boys boarding school St Joseph's College, which his great-grandfather Paddy Condon, an Italian immigrant and master stonemason, helped build.

His first break was as an infantry soldier, rifleman, stretcher bearer, and ambulance driver in the 5th/7th Battalion, Royal Australian Regiment, Australia's regular army from 1982 to 1985.

While at university, he decided to record an album of children's music, enlisting the assistance of fellow student and guitarist Murray Cook, former Cockroaches roadie and vocalist Greg Page, former bandmate and keyboardist Jeff Fatt, and Macquarie instructor and composer Phillip Wilcher, who later left the group.

[14] Page ended up wearing a yellow shirt and Field originally wore a green polo shirt, but changed to blue to avoid clashing with Dorothy the Dinosaur.Each Wiggle developed a "schtick" based on their actual behaviours, which evolved into caricatures, and served the same purpose as the uniforms in differentiating their characters and making them memorable to young children; Field's was eating.

[17] By mid-2004, shortly after his marriage and the birth of his first child, Field's serious medical issues, worsened by their heavy tour schedule, caused him to consider quitting or re-inventing the Wiggles, despite their great success in the U.K. and North America.

He remained in the group because he wanted to continue to educate children and as Wiggles manager Paul Field stated, "to placate American, British and Canadian business partners".

[25] Beginning in 2007, Field, who is a registered breeder of Miniature Fox Terriers,[26] did voiceover work for the TV show RSPCA Animal Rescue for Channel 7 in Australia.

[34][35] He has stated that "being on the road is a dangerous job for someone with depression", but has dealt with it through diet, exercise, talking about it, and having a good support system (including his father before his death in 1998,[36] his wife, and his friend Murray Cook, among his bandmates).

[37][38] Field is a devout Catholic,[23][29] something that he reported helped him deal with his chronic health issues and depression, especially the spiritual practices of prayer and devotion to the Virgin Mary as expressed by Our Lady of Guadalupe.

[31] He admits that he got his tattoo of the Virgin, which he hid from fans for a long time, during a visit to Mexico while on tour in North America, in the middle of a bout with chronic pain and dental problems, as he put it, "in a moment of madness".

[40] Field was made a Member of the Order of Australia on 26 January 2010 "for service to the arts, particularly children's entertainment, and to the community as a benefactor and supporter of a range of charities".