Williamson usually writes and performs songs that relate to the history and culture of Australia, particularly the outback, in a similar vein to Slim Dusty and Buddy Williams before him.

[3][4] His parents farmed wheat crops on various small land lots in the region and both were amateur performing artists singing in local Gilbert & Sullivan productions.

[5][7] In 1969 John Williamson wrote a novelty song, "Old Man Emu", and early the following year he performed the track on TV talent quest, New Faces, winning first place.

Williamson's follow-up single, "Under the Bridge" backed with "The Unexplored Shadows of Mine" was issued in November[9] with certain pressings having its A and B-sides swapped around.

[9] In 1973 Williamson hosted a country music TV series, Travlin' Out West, which ran for two years, broadcast by NBN-3, Newcastle.

Also that year Williamson formed a country music band, Crow, which performed on the pub and club circuit across Australia.

In early 1981 John Williamson's rock group, Sydney Radio, disbanded and he began playing solo in pubs, which attracted more new fans.

[14] "The Breaker" enabled Williamson to cast off the "Old Man Emu" novelty tag and "[h]is long apprenticeship flowed into an apparently endless set of songs charming Australians with stories and images about themselves and their country".

As a bonus, Williamson collaborated with both of his daughters, Ami and Georgie, and with Australian folk group Bullamakanka on "Goodbye Blinky Bill" – highlighting the comic koala character of the same name.

To support Mallee Boy Williamson performed his concerts in a campfire setting and since that time he commences many of his shows with its title track.

[23] Despite the title song's lyrics, Williamson has told concert audiences that he did not actually meet his future wife, Mary-Kay, in The Boomerang Café but actually by a water tank.

[29] It was launched in January 1992 with Dusty as inaugural chairman and Williamson as vice-chairman and later that year CMAA took over the organisation of the Country Music Awards of Australia – established in 1973 – from radio station, 2TM based in Tamworth.

At the Country Music Awards of Australia in January 1995, he won 'Video Track of the Year' for "Tropical Fever" – directed by Mark Jago.

The next two tracks, "Frangipani Bay" and "Cape York Peninsula", were written during a road trip to Australia's most northern point.

"Buried in Her Bedclothes" was written after Williamson and Mary-Kay, his spouse of the time, met an elderly woman on an Indian Pacific rail trip.

On 12 October, Williamson was asked by the Prime Minister, John Howard, to perform "Waltzing Matilda" at the Memorial Service for the first Anniversary of the 2002 Bali bombings.

[40] In discussing John's wife of the time, the opening track, "Little Girl from the Dryland", describes Mary-Kay and her childhood in Tulloona Bore, south of Boggabilla, from her point of view.

"Bells in a Bushman's Ear" is a tribute to Australia's country music forefathers, and "The Camel Boy" is about the life of indigenous artist, Albert Namatjira, who is Warren H Williams' great uncle.

"Keeper of the Stones", which first appeared on Williamson's live album and DVD of 2004, Mates on the Road, was dedicated to indigenous Australians of The Stolen Generation.

Also on Chandelier of Stars is "A Country Balladeer" which is a duet with Chad Morgan, and "Flower on the Water" is a tribute to the victims of the Bali bombings.

The first four lines are inspired by words on a photo of a deceased victim: "To hear your voice, to see you smile / To sit and talk to you awhile / To be together the same old way / That would be our greatest wish today".

He was evidently emotional while performing both "Home Among the Gum Trees" and "True Blue" at Irwin's memorial service inside the arena of his Australia Zoo Crocoseum.

Wildlife Warriors was additionally released in November 2006 on a compilation album of the same name, along with twelve of Williamson's favourite conservation awareness tracks and his two live performances from Irwin's memorial.

Subsequent singles that followed were "Cydi", "Drink a Little Love", "Australia Is Another Word for Free" as a trio with Williams and Amos Morris, and "Better Than a Picture".

The Hillbilly Road album was promoted everywhere around Australia until early the next year when Williams decided to move on and pursue other musical projects, leaving Williamson to perform the rest of the tour solo.

On 26 January (Australia Day) 2010 Williamson released a new Australian anthem called "Island of Oceans" as a duet with Shannon Noll.

At a press conference for the album in Tamworth on 21 January hosted by the then Governor-General Quentin Bryce, in his acceptance speech, John expressed his gratitude for the longevity of his career up to that point, in the process thanking his fans, friends and family, including his first wife, Mary-Kay.

In 2014, Williamson released his fiftieth album (including compilations) called Honest People, as well as writing his autobiography, issued by Penguin.

[45][46] In January 2025, Williamson announced a continuation of his 55 Years – My Travellin' Days Are Done tour and his 21st studio album How Many Songs will be released in April 2025.

[55][56] "Call Me Blue" from the nineteenth album, Honest People, was written in reaction to the verbal abuse that Williamson received after resigning as president of the CMAA.