Field was born in Kellyville, New South Wales, Australia. He is the youngest of seven children, and grew up in north western Sydney. He came from a long line of musicians, especially the women in his family. 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. Field’s mother, Marie, made sure that all of her seven children learned how to play at least one musical instrument. 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. In 1979, while they were students at St. Joseph’s, he and his brothers Paul and John formed the pop group the Cockroaches.

He was inspired by his sister Colleen to study early childhood education, and became convinced that teaching preschool children “was my calling”. He was also attracted to the profession’s freedom, artistic nature, and lack of discipline, which was different from his experience in boarding school. Field put off university when the Cockroaches became successful, but he was dissatisfied with touring and plagued by “perhaps irrational, but very real, feelings of inadequacy and depression”. By his mid-twenties, he decided that he did not want to tour any longer, so he took two breaks. 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. He played the bagpipes in parades and on training missions, but ended his military service in July 1985 and suffered from a bad back as a result of his training. He also went backpacking in the U.K., listening to roots music, to children’s music by artists like Raffi, and to recordings of children’s books.

The Wiggles recorded their first CD in 1991; it sold 100,000 copies. Field worked as a preschool teacher for two years before the success of the Wiggles and their extensive touring schedule, which he strongly disliked, forced him to quit. After the production of their second album, the Wiggles adopted colour-coded shirts to wear on stage. According to Field, he wore blue because Cook and Fatt already owned shirts in their colours of red and purple respectively, so he and Page “met in a Sydney department store and literally raced to see who got the blue shirt”. 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. Field created and played the original Captain Feathersword; the role was taken over by Paul Paddick in 1996. Field also played Wags the Dog.

Field went public about his experience with clinical depression in mid-2007 to draw more attention to the condition. 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, his wife, and his friend Murray Cook, among his bandmates). He chronicled his health struggles and how he overcame them in his 2012 book How I Got My Wiggle Back.

In 1999, Field was named “Bachelor of the Year” in Cleo Magazine. In 2003, he married Michaela Patisteas, a former dancer whose family owned Griffiths Coffee in Melbourne. They have three children, who have joined the Field family business by appearing in several of the Wiggles’ TV shows and videos. Beginning in 2007, Field, who is a registered breeder of Miniature Fox Terriers, did some voiceover work for the TV show “RSPCA Animal Rescue,” for Channel 7 in Australia.

By the mid-1990s, despite the success of the Wiggles, Field reported being suicidal and “frequently gripped by anxiety, sadness, and negativity”. 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. After meeting chiropractor James Stoxen in Chicago in 2004, Field improved his health to the point that he was able to continue. He began to hire teams of chiropractors for himself, his fellow bandmembers, and castmembers in every city they performed, which he credited with making it possible for them to fulfill their touring requirements. In early 2013, Field became the only original member of the group to remain after Fatt, Cook, and Page retired. 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”.

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”.

In 2018, Field, along with fellow Wiggles member Lachlan Gillespie and band members Oliver Brian and David O’Reilly, started a band for adult fans called the Unusual Commoners, which played a mixture of traditional Australian, Irish, Scottish and folk songs. They performed their first international show in St. John’s, Newfoundland in late 2018.

In July 2020, he and the other classic Wiggles appeared in the Soul Movers music video for “Circles Baby”.