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The Background
If you ever want to start a fight in a roomful of Australian ballad researchers, just mention this song. Some believe its roots lie in a rewrite of Bold Jack Donohoe, others that it's Jack Doolan, an entirely different 19th Century bushranger, who the song has in mind.
"It's one of those songs where I'm sure we'll never know for sure," the Australian song collector Jason Roweth told me. "If I had 20 folklorists from Australia here with me right now, the best people I know, they would split down the middle and they would argue into the night."
We'll get into the details of that argument in a moment, but first let's remind ourselves of the song's lyrics. I've mixed and matched my own favourite WCB verses from Ron Edwards' and Warren Fahey's books to assemble the version here. ⁽¹⁾

The Ballad
There was a Wild Colonial Boy, Jack Doolan was his name,
Of poor but honest parents he was born in Castlemaine,
He was his father's only hope, his mother's pride and joy,
And dearly did his parents love the Wild Colonial Boy.

At the early age of 16 years, he left his father's home,
And through Australia's sunny climes a bushranger did roam,
He robbed the wealthy squatters, their flocks he did destroy,
And a terror to Australia was the Wild Colonial Boy.

Chorus
So come along, my hearties, we'll roam the mountain side,
Together we will plunder, together we will ride,
We'll scour along the valleys and gallop o'er the plains,
For we scorn to live in slavery, bound down with iron chains.

In 'sixty-one, this daring youth commenced his bold career,
With a heart that knew no danger, no foeman did he fear,
He stuck up Beechworth's mailcoach and he robbed Judge MacEvoy,
Who, trembling cold, gave up his gold to the Wild Colonial Boy.

One day, as he was riding the mountainside along,
A-listening to the kookaburra's pleasant laughing song,
He spied three mounted troopers: Davis, Kelly and Fitzroy,
With a warrant for the capture of the Wild Colonial Boy.

[Repeat chorus.]

"Surrender now, Jack Doolan, you see there's three to one,
Surrender now, Jack Doolan, you daring highwayman!"
Jack drew a pistol from his belt and spun it like a toy,
"I'll fight but not surrender," cried the Wild Colonial Boy.

He fired at trooper Kelly and he brought him to the ground,
And, in return from Davis, received a mortal wound,
All shattered through the jaw he lay, still firing at Fitzroy,
And that's the way they captured him, the Wild Colonial Boy.

The Facts
In its earliest form, WCB seems to have been not the concise, punchy song we have today, but a rather long-winded ballad following the tradition set by its British and Irish forbears.
As evidence of this, we a 1927 newspaper column by the Australian journalist Julian Stuart. There, writing of events "about 50 years ago", he says: "The Wild Colonial Boy was popular, but it's length was tiresome; it had 157 verses". There's an element of comic exaggeration there but his meaning's clear enough. The poet HH Booth makes a similar point in a few sarcastic lines from 1909: "Then to add to our joy / Gregory Bill sang twenty verses of / The Wild Colonial Boy." ⁽²⁾
The song's also mentioned in a Queensland newspaper's ghost story, published in September 1879. The story's about a young man called Joseph who liked to sing bushranger songs to his companions. "He used to regale them on various occasions with the adventures of the 'Wild colonial boy, Jack Dowling was his name'," the story says. "[The song] describes his parentage, his wild career and his untimely and lamentable death at the hands of the police." ⁽³⁾
William O'Neill knew it at around this time too. "As a boy in the [1870s] I heard it sung and learned it at the campfires of teamsters and shearers travelling to the sheds of Victoria, New South Wales and Queensland," he told the Ned Kelly scholar Clive Turnbull. "It was in those times the most popular of all the old bush songs. It was carried afar by word of mouth, there being no printed version known. The versions varied slightly, but all agreed on the basic facts." ⁽⁴⁾
WCB was also sung at the Glenrowan Inn siege in 1880 where Kelly was finally captured - the singer this time being a 13-year-old boy called Johnny Jones. By now, we seem to be talking about a severely truncated version of the monster ballad Stuart mentions, cut to something like the tight six or seven verses we have today.
Exactly when that happened, I don't know - most likely the two songs existed in parallel for a while - but there was never any doubt which version would prevail. When its first printed set of lyrics appeared in an 1881 collection called The Colonial Songster, the song had just five verses. By 1905, when Banjo Paterson included it in his book Old Bush Songs, it had acquired the additional chorus used above, and that's more or less the form it's remained in ever since. ⁽⁵⁾

One fact the different versions disagreed on was the name of the song's hero. Anderson's book gives five different sets of WCB lyrics, which variously call him Jack Doolan, Tom Dowling, Jack Duggan, Jim Doolin and John Doolin. Ron Edwards adds the slight variation Jack Dolan in one of his lyrics from Australian Folk Songs.

The only version I've seen which explicitly mentions Jack Donohoe, the notorious 1820s bushranger, requires a slightly awkward rewrite to accommodate his extra syllable in his name: "There was a wild colonial boy, Jack Donohoe by name". And yet, until only about 15 years ago, all the conventional wisdom insisted that Donohoe was the ballad's true subject.
Supporters of this view wave away all the alternative names used by claiming Donohoe's own ballad had become far too dangerous to sing because the convicts' masters saw it as a sign of insurrection. In response to this, they argue, the convicts cleverly substituted another name and turned what had once been specifically a Donohoe ballad into a generic tribute to all who shared his rebellious spirit. ⁽⁶⁾
"I tend to favour the idea that Donohoe turned into The Wild Colonial Boy, in the sense that I trust some of the giants of Australian folklore who believed that was the case," Roweth told me. "But I'm also the first to say, look, it's only an impression that I get."
One of those giants is Donohoe's biographer John Meredith, who concluded in 1960 that one or other of the Donohoe ballads "gradually evolved into [.] The Wild Colonial Boy." It's certainly true that both songs can be sung to the same tune, and that both have come to share an almost identical chorus. Sceptics reply that folk songs borrow tunes and choruses from one another all the time, and ask just what this traffic between the two songs is supposed to prove anyway.

Much more compelling is the story told in WCB's last two verses. Many of the details here precisely match the real Jack Donohoe's fate, including the fact that the troopers had him outnumbered, their call for him to surrender and his scornful rejection of that offer. His defiant cry of "I'll fight but not surrender" in the WCB lyrics above directly echoes these lines from an early version of Bold Jack Donohoe:

"Resign? No, no. I never will, unto your cowardly crew,
Today I'll fight with all my might," cried Bold Jack Donohoe.

Set against that, there's the fact that the real Donohoe was shot by a trooper called Muckleston - not Davis as WCB maintains - and that the only other troops named in his inquest reports are called Gorman and Hodson. He did die of a head wound, though the bullets entered his neck and forehead rather than his jaw.
The Australian folklorist Keith McKenry believes WCB had an independent existence of its own long before that Jack Donohoe chorus made its way across to the other song. "The ballad about Donohoe got confused later in the piece with The Wild Colonial Boy - largely because the ballads had this shared chorus," McKenry told me. But there's one crucial difference, which this comparison illustrates:

Bold Jack Donohoe
Then come along, my hearties, we'll roam the mountains high,
Together we will plunder, together we will die.

The Wild Colonial Boy
So come along, my hearties, we'll roam the mountain side,
Together we will plunder, together we will ride.

"Donohoe was on foot, of course," McKenry points out. "He never had a horse. When that chorus gets added to The Wild Colonial Boy they start riding, so that's the major difference." This reflects the clear distinction between the bushrangers of Donohoe's 1920s generation, who held up slow-moving bullock carts on foot, and the mounted bushrangers who robbed prospectors during the country's 1850s gold rush.

It's also worth noting that both of the real-life crimes mentioned in WCB - 1859's famous Beechworth mail coach robbery and the bailing up of Judge Michael Macoboy about three years later - came three decades after Donohoe's death. By 1861, when we're told the boy "commenced his bold career", Jack Donohoe had already been in the ground for 30 years. Not only that, but we know that he was actually born in Dublin, not in Castlemaine as the song insists. ^{(7, 8)}
"There's been a lot of confusion about whether Donohoe was the Wild Colonial Boy," McKenry admitted when I called him at his home in Central Victoria. "Then this fella found a reference to John Doolan in a Castlemaine newspaper, who was clearly - clearly - the inspiration for The Wild Colonial Boy. There's no question about that." We'll get to the fella in question in a moment, but first let's consider the issue of just which Castlemaine it is we're talking about.

The Irish Castlemaine, a small town in County Kerry, calls itself "the birthplace of the wild colonial boy" and has named one of its pubs "Jack Duggan's Bar" in his honour. "Home of the Wild Colonial Boy," a postscript on the pub's sign notes. In September 2018, the village announced plans to erect a life-size bronze statue of Duggan, dressed in full bushranger gear, to celebrate this legacy.
The mention of Castlemaine in the song's lyrics has also inspired many Irish acts to record it, including the Clancy Brothers & Tommy Makem, who took their version round the world in the early 1960s with this opening couplet: "There was a wild colonial boy, Jack Duggan was his name, / He was born and raised in Ireland in a place called Castlemaine."
Not much room for ambiguity there. Unfortunately for the County Kerry tourist board, however, there happens to be another Castlemaine in the Australian state of Victoria - and it's the Australian one which has a far stronger claim to both the song and the man who inspired it. No wonder Ron Edwards, the Australian song collector, found not a single British or Irish example of WCB when he searched the two countries' ballad archives in 1985. In all likelihood, he concluded, the song is an Australian composition which only later found its way back to Ireland. ⁽⁹⁾
Dozens of Irish singers and bands have recorded WCB since the Clancy Brothers popularised it, almost always with those same two opening lines. "Jack Duggan" is most likely a corruption of the original song's "Jack Doolan", but has proven a popular enough variant to feed back into some Australian versions of the song too. That's the way Anderson heard in sung in a bar during his 1960 trip to Australia's Thursday Island, and that's the way the Australian actor Bill Kerr sings it in an old episode of Hancock's Half Hour too. ^{(10, 11)}

"It's pretty obvious to me," McKenry said when we discussed this issue. "The Clancy Brothers came to Australia in 1963. When they sang the song, they just changed one of the lines to 'He was born and raised in Ireland.'. That's just what you do if you're a singer. But I'd probably get my nose punched in if I went to Castlemaine in Ireland and said the song wasn't about someone from their town." ⁽¹²⁾
Ireland's real contribution to the song lies not in its geography, but in the two tunes it most often adopts. Like Bold Jack Donohoe, WCB was first sung to the tune of the old Irish rebel song The Wearing of the Green, which made it particularly popular among the downtrodden Irish transportees and labourers who first spread it round Australia.
A second tune, which song collector AL Lloyd calls "a doleful waltz", was contributed by the Irish songwriter Percy French (1854-1920), who also wrote The Mountains of Mourne and Abdul Abulbul Amir. It's French's setting that's used by both Mick Jagger when he sings WCB in the 1970 movie Ned Kelly and by John Wayne's pub companions in 1952's The Quiet Man.

The man who turned WCB scholarship upside down was an Australian maritime historian called Granville Allen Mawer - and his researches started with our old friend Judge Macoboy. Did the facts support the idea that he was the real-life figure behind Judge MacEvoy in the song?
Mawer established that Macoboy was appointed to the Victoria County Court bench in 1858 and continued working there until his death in 1872. He heard cases in both Maryborough and Bendigo, two towns within a mere 30 miles of Jack Doolan's stated birthplace. This gave Mawer both a manageable period to research and some target newspapers to concentrate on. Bendigo's Evening News, Advertiser and Independent all proved particularly helpful. Most of what follows about Jack Doolan's life I've learned from Mawer's 2004 book The Wild Colonial Boys, which I heartily recommend to anyone interested in the song. ⁽¹³⁾
William Dooling, who would later become Jack's father, was transported from Ireland to Van Diemen's Land (now Tasmania) on a convict ship in 1848. He'd been sentenced to seven years for robbing a house in Tipperary. Ann Burke, who'd been convicted of a Wexford burglary, was sent to Tasmania on a seven-year sentence of her own the following year. They became a couple, and Ann bore William his first child in 1852. In the course of the next 14 years, she'd give him six more, the full roster reading: William (born 1852); Catherine (1853), John (1856), Thomas (1859), Patrick (1861), James (1863) and Annie (1866).
It's their third child, then known as John Dooling, who interests us here. In the newspaper reports and prison records which allow us to piece his life together, he's variously referred to as John Doolan, Jack Doolan and James Doolan, so I'm simply going to call him Jack throughout for the sake of clarity.⁽¹⁴⁾

In the early 1860s, with both William and Ann's sentences now complete, the whole family moved to the goldrush town of Bendigo, where William hoped to become a successful gold miner. He had no luck with that endeavour, so he and Ann began running what Mawer calls " a sly-grog shanty" in Barnard Street - an illegal pub, in other words. Jack took little interest in his schooling, passing the time with petty mischief and vandalism instead. When he turned 12, his father apprenticed him to a local shoemaker called Joseph Abbot. His first serious run-in with the law came on January 8, 1869, when he stabbed a fellow apprentice at work.
Jack had been cleaning the bottom of a boot with a broken old knife when John Zahner came over and claimed Jack had stolen the knife from him. He demanded Jack lend him his knife in return, but Jack refused, saying Zahner would blunt it. Zahner - who was three years older than Jack - snatched the broken knife from him and gave him a shove. "[This quarrel] resulted in Doolan rising from his seat and walking across to a bench, where he took his clasp knife from his pocket, opened it, then ran over to Zahner and stabbed him," January 20's Bendigo Advertiser reported.
One of the other apprentices saw blood was now oozing from Zahner's belly, so he called Abbot over to deal with the matter. Abbot asked Jack what the hell he thought he was doing, and Jack replied that he wouldn't be called a thief by anyone. When Abbot shot back that it was worse to be called a murderer, Jack said it would have served Zahner right if the stab wound had killed him. A Dr Betham, who was summoned to dress the wound, said it was only Zahner's leather apron which had stopped the blade doing serious damage.
Jack was arrested for grievous bodily harm and held in custody, the police recording his name as "John Doolan". It came out at the February 13 trial that Zahner had been bullying him for some time, calling him a thief, a loafer and an "Irish pig", but Judge Sir William Stawell showed no mercy. He sentenced Jack to 12 months imprisonment, the first two weeks to be served at Sandhurst's adult jail and the rest on the reformatory ship Sir Harry Smith in Hobson's Bay. It's his admission records there which give us the fact that he was born in Castlemaine.^{( 15, 16)}
While on the ship, Jack struck up a friendship with Ned Donnelly, a boy a year older than him who'd stolen a bridle and saddle near Axedale. He'd taken the horse wearing them too, but prosecutors had agreed to drop that more serious charge because Ned was only 13 at the time. He was nine months into his own five-year sentence when he met Jack.

Jack was released in February 1870. Three weeks later, Ned escaped from the reformatory ship and started calling himself William Jones, a name he'd borrowed from another inmate. He and Jack teamed up again and, by December 1871, they were preparing to set off on a career of bushranging together. They began by stealing Patrick Hehir's suit of clothes and two shirts from his labourer's hut at Huntly, then helped themselves to a chestnut horse which its blacksmith owner John Steer had just turned out to graze on Axedale Common.
On New Year's Eve 1871, they kicked things up a notch by deciding to rob a local widow at gunpoint. Bridget Foley, who lived alone on a smallholding near Axe Creek, was half undressed and about to go to bed when she heard Jack and Ned pounding on her door. If she didn't let them in, the two boys shouted, they would simply break the door down.
"[Widow Foley] was compelled to let in the young ruffians, who intimidated her with some firearms they had in their possession," said the Bendigo Advertiser. "Having gained admittance, the boys began to ransack the house, and they turned it upside down before they desisted. They failed to meet with anything valuable, and were contented with stealing a pair of fowl and a tea canister with a few other domestic articles." ⁽¹⁷⁾
Despite the plural "firearms" there, the boys had only one pistol, and it was Ned who handled that. Foley later testified that she'd been very scared. "[Ned] was cursing and swearing all the time, and they threatened to criminally assault her," the Bendigo Advertiser noted. "They presented arms and said 'If you don't deliver up what money you have we will take your life'." Foley scrabbled round for what little cash she had - it amounted to only three or four shillings - and gave the boys that to add to their modest haul. Only then did they leave her in peace.
Ned and Jack carried out several more small thefts in the week that followed, grabbing some food and cooking utensils for their planned new life in the bush. All they needed now was a cart to carry their new gear around in.
At first light on January 9, 1872, they rode Steer's horse up to Patrick Hallinan's farm on the Campaspe River. Patrick Donohue, one of the farm's workers, woke up when he heard them rooting around in the stables next to his room. Rushing outside to see what was going on, he found Ned and Jack harnessing Steer's horse to Hallinan's spring cart.
"The boys said they were 'only going to have a loan of the cart and harness'," the Bendigo Advertiser told its readers. "Patrick, however, was not inclined to approve of the arrangement and was about to create an alarm, when he was horrified to hear one of the boys say to the other, 'Blow out his brains'. Instantly he found himself under cover of a pistol, charged and capped. He was utterly overcome with fear, nor did he attempt to say or do anything until the robbers had mounted their cart and were leaving the farm-yard." ⁽¹⁷⁾

As soon as Ned and Jack were out of sight, Patrick ran to tell his employer the cart had been stolen by two armed men. Hallinan saddled up his own horse and galloped off in pursuit, sticking to the bush rather than the roads to ensure the thieves didn't see him. He followed the cart as far as a crossroads near Huntly, watched it take the Bendigo road, then hurried into Huntly itself to alert a constable called William Davidson, who joined him in the pursuit.
They caught up with the cart by the Robin Hood Inn about 12 miles outside Bendigo and Davidson forced it to stop. "They seemed very much frightened at the sudden and unexpected manner in which their glorious career was brought to a close," the Bendigo Advertiser reported next day. "On one of them was found the pistol which had so terrified Donohue. It was still charged, capped and ready for action, and it is only surprising they did not try to intimidate Davidson in a similar manner. [.] The boys did not attempt to resist, but cowered down before the trooper, and quietly allowed themselves to be handcuffed."
The pair were locked up in a watch-house at Sandhurst, where Jack learned that his younger brother Patrick had fallen in some water and drowned on the previous day. He was still weeping bitterly at this news as the cell door slammed behind him. Their trial was set for February 19, with Justice Edward Williams presiding and the two defendants named as "William Jones and James Doolan". Jack was still only 15 and Ned just a year older, so the newspapers dubbed them "The Larrikin bushrangers". Angry editorials deplored the depravity of modern youth and demanded a crackdown. ⁽¹⁸⁾
There were four charges against Ned and Jack: breaking, entering and stealing from Hehir's home; stealing Steer's horse; the armed robbery of Widow Foley and stealing under arms from Hallinan. All four victims gave evidence against them, and the jury's verdict was never in doubt. Jack was found guilty on the last three charges and Ned on all four - the distinction being that it was he, not Jack, who'd forced the window of Hehir's hut and climbed inside to steal the clothes.

When the time came for sentencing, Judge Williams decided to make an example of them. Each boy would serve two years for horse-stealing, six years for robbing Widow Foley and another six years for stealing Hallinan's cart. Ned got another three years on top of that for house-breaking. All the sentences were to be served consecutively, which meant a total of 14 years in prison for Jack and 17 for Ned. Because both had passed their 15th birthdays, they would do their time in Pentridge, an adult prison.
"Quite a scene occurred in the court when their sentences were passed," the Bendigo Independent confided. "The mother of the prisoner Doolan, who had patiently sat in the courts during the committal and conviction, stood in the body of the court, and the grief of the poor woman when her wayward son was led from the dock defies description. For several minutes her loud cries of distress at having 'reared a son for such an end', completely prevented the business of the court from proceeding." The noise she made that day was "a heartrending shriek", one reporter said. Another called it "a piercing lamentation". ^{(19, 20)}
Perhaps it was Ann's suffering which prompted a change of heart in the newspapers. Just two years earlier, they pointed out, the notorious adult bushranger Harry Power, who unrepentantly boasted he'd carried out 60 robberies, had been given just 15 years. Ned and Jack's treatment looked very harsh next to that.
"The boy Jones is undoubtedly a remarkable young desperado,' said the Bendigo Independent. "[But] we would ask whether the boy or society will be benefitted by his seventeen years incarnation? One generation of prisoners after another will be his companions and, if he does not come out of gaol an utterly ruined reprobate, it will not be the fault of the Judge who sent him to such a school for such a term. His companion in crime was let off a little easier, but with regard to both of them there is an unpleasant impression that they were dealt with more severely than men would have been." ⁽²¹⁾
There was talk of organising a petition to demand clemency for the two boys, but nothing came of it. By "clemency" what most people meant was sparing them a lengthy jail term but giving than a damn good whipping instead. By the standards of the day, that was felt to be a kinder punishment in the long run.
On February 28, barely a week after Jack's sentencing, his eight-year-old brother James was convicted of stealing a cage from a Mr Young - presumably a birdcage - and sentenced to a five-year term of his own on the reformatory ship. "For Ann Dooling, having lost three sons in seven weeks, it must have seemed the end of her family," Mawer writes.

Jack's prison records tell us he was just over five feet tall and weighed a little under eight stone when he entered Pentridge. He had a sallow complexion, dark brown hair, brown eyes , a freckled face and buck teeth. His experience as a cobbler meant he was sent to the prison's shoemaking shop rather than being forced to break rocks in the yard. He'd kept his nose pretty clean while on the Sir Harry Smith, but now he seemed to decide he might as well become the bad lad everyone assumed him to be.
Mawer's research reveals over 30 punishable offences Jack committed in prison. These include possession of various contraband (such as tobacco, obscene drawings, knives and a hacksaw), refusing to obey the guards' orders and assaulting his fellow prisoners. Talking, whistling and dancing in his cell condemned him to two days' solitary. "As he was already in separate confinement, [that] meant bread and water in a punishment cell underground, totally devoid of light, sleeping on the bare floor," Mawer explains. "His longest spell in solitary was ten days."
Jack also spent two months in irons for threatening to stab one of the prison guards and, in August, managed to excavate half a ton of soil from the floor of his cell before his planned escape tunnel was detected. Small wonder the Argus pronounced him "one of about 30 of the worst prisoners at Pentridge". ⁽²²⁾
Meanwhile, Jack's family were pressing on with their own lives. His mother Ann seems to have run a brothel while he was inside, with Jack's big sister Catherine among the girls working there. An 1872 court case against one of the brothel's customers produced credible accusations that William was beating his wife. Thomas, who was three years younger than Jack, was killed in a gory accident while working on the trains in 1876. By the following year William and Ann had separated, though he continued to pursue her with violent threats. ⁽²³⁾
Jack walked out of Pentridge Prison on August 13, 1882, having served "just" 10½ years of his 14-year sentence. He decided not to reconnect with his family, but to move to what's now the Melbourne suburb of Hawthorn instead. Wanting a fresh start, he began calling himself "Jack Dowling" and started work as a tobacconist and barber there. In 1885 he married Amelia Watkins, though only her family was present at the ceremony. They had a daughter, also named Amelia. in June 1887, by which time Jack was already dying of TB. He passed away on June 21 and was buried in the Watkins' family plot at Melbourne's General Cemetery. Baby Amelia joined her dad there just five months later. ^{(24, 25)}

Now that we have Jack's life story - and let me stress again that it's only thanks to Mawer's book that we know any of this - it's time to return to the song. How closely does it match Jack's real biography?

Verse 1
There was a Wild Colonial Boy, Jack Doolan was his name,
Of poor but honest parents he was born in Castlemaine,
He was his father's only hope, his mother's pride and joy,
And dearly did his parents love the Wild Colonial Boy.

Jack's real surname was Dooling, but we know police and prison authorities recorded it as "Doolan" from his first arrest in 1869 till his final release from Pentridge 13 years later. Jack and John were more or less interchangeable as Christian names in many families at the time, so that's a perfectly reasonable transcription too. His parents were certainly poor - though not noticeably honest - and we have the evidence of a note in his family Bible to establish he was born in Castlemaine. Her outburst in the court suggests his mother loved him well enough, but his father's affection is a little more doubtful. As Mawer points out, William more or less washed his hands of the boy in 1870.

Verse 2
At the early age of 16 years, he left his father's home,
And through Australia's sunny climes a bushranger did roam,
He robbed the wealthy squatters, their flocks he did destroy,
And a terror to Australia was the Wild Colonial Boy.

In fact, Jack was only 15 when he embarked on his short-lived bushranging career. It's true he was a teenager, though, and that's the important point here. Far from roaming Australia's sunny climes, he carried out all his robberies within a few miles of his Bendigo home. No flocks were destroyed and most of his victims had barely more money than Jack himself. It was Ned who terrorised Widow Foley and Patrick Donohue with the gun, not Jack, and those two hold-ups hardly amount to a continent-wide spree.

Chorus
So come along, my hearties, we'll roam the mountain side,
Together we will plunder, together we will ride,
We'll scour along the valleys and gallop o'er the plains,
For we scorn to live in slavery, bound down with iron chains.

We've dealt with this chorus already. Aside from that small amendment to acknowledge Jack had a horse, it seems to have been imported wholesale from Bold Jack Donohoe.

Verse 3
In 'sixty-one, this daring youth commenced his bold career,
With a heart that knew no danger, no foeman did he fear,
He stuck up Beechworth's mailcoach and he robbed Judge MacEvoy,
Who, trembling cold, gave up his gold to the Wild Colonial Boy.

Actually, it was 'seventy-one, but we'll let that go as it would have messed up the scansion. Whatever his other faults, Jack does not seem to have been short of courage, so "no foeman did he fear" makes sense too. There are two possible sources for the Beechworth mail coach reference: the 1859 job I mentioned above (when Jack was just three years old), and a Porepunkah hold-up by Harry Power in May 1869 (when Jack was doing time for the Zahner stabbing). He'd have been only six years old when the real Judge Macoboy was robbed in 1862, so I think we can exonerate him there too. These are just random bushranging incidents inserted into Jack's song for the sake of filling out a verse and providing a convenient rhyme.

Verse 4
One day, as he was riding the mountainside along,
A-listening to the kookaburra's pleasant laughing song,
He spied three mounted troopers: Davis, Kelly and Fitzroy,
With a warrant for the capture of the Wild Colonial Boy.

No-one's ever been able to identify the "Davis, Kelly and Fitzroy" mentioned here, either in Jack's life or any other bushranger's tale. The trooper who actually captured Jack was called Davidson. Far from the police outnumbering the desperados - as standard bushranging lore demands - it was the other way round. The name Fitzroy was probably chosen simply because it rhymes with "boy".

Verse 5
"Surrender now, Jack Doolan, you see there's three to one,
Surrender now, Jack Doolan, you daring highwayman!"
Jack drew a pistol from his belt and spun it like a toy,
"I'll fight but not surrender," said the Wild Colonial Boy.

"Spun it like a toy" is a nice touch as it reminds us again that Jack was really just a child.

Verse 6
He fired at trooper Kelly and he brought him to the ground,
And, in return from Davis, received a mortal wound,
All shattered through the jaw he lay, still firing at Fitzroy,
And that's the way they captured him, the Wild Colonial Boy.

As we've seen, Jack and Ned made no effort to resist Davidson, not even levelling their pistol at him, but meekly surrendered. No shots were fired and no wounds received. These last three verses are all a much closer fit for how Jack Donohoe met his end, and their sentiments are included as a matter of course in just about every bushranger ballad you find.
So: there we have it. The Wild Colonial Boy relates aspects of the real Jack Doolan's life with reasonable accuracy, but mixes them with several verses about his predecessor Jack Donohoe and a quick reminder of Harry Power's career. No matter what the Clancy Brothers lyrics might tell you, its hero was not born in Ireland, but half a world away in Victoria State.
None of that stops it being a great song, of course - one of the two or three best that Australia's ever produced - and the core of its appeal is plain enough. As Manifold points out, WCB elbowed aside the old convict songs like Bold Jack Donohoe to give native-born Australians a hero they could call their own. "Donohoe meant very little to the free settlers of Australia; a colonial hero could mean a great deal," he points out. Here was a figure who embodied all the cheeky rebellion and determined independence Australians liked to feel typified their own lives. Jack's avatar in the song lives his whole life as what Mawer calls "a celebration of liberty", and who wouldn't want to sing about that?

The Music
The artists who've recorded The Wild Colonial Boy include the Aussie Bush Band, The Clancy Brothers, Dr Hook, Burl Ives, Mick Jagger, AL Lloyd, Gary Shearston and Norma Waterson. Spotify has many other versions too, but they're mostly extracted from albums with titles like "25 Irish Blarney Pub Singalong Favourites" and so best avoided.
You can hear the Lloyd, Shearston and Waterson versions on the Spotify playlist I've called PlanetSlade Bushrangers. The Pogues borrowed WCB's tune for Jack's Heroes, their 1990 World Cup song with The Dubliners, so I've thrown that in as a little bonus.

Sources & Footnotes
1) Verse two here is taken from Warren Fahey's 2010 book Australian Folk Songs & Bush Ballads, and all the other verses from Ron Edwards' 1991 book Great Australian Folk Songs. The kookaburra reference is from Fahey as well, where it replaces Edwards' mention of "the little birds". I prefer the Fahey here because it's both less twee and more specific to Australia.
2) Part of the Glory: Reminiscences of the Shearers' Strike, Queensland, 1891, by Julian Stuart (Sydney Australian Book Society, 1967).
3) St George Standard & Balonne Advertiser, September 20, 1879.
4) O'Neill's letter to Turnbull is quoted in The Story of Australian Folk Song by Hugh Anderson (Ram's Skull Press, 1970).
5) The Colonial Songster, edited by Mr J Small (AT Hodgson, 1881). This version calls the boy "Jack Dowling".
6) That's not to say the supposedly safe version of the song couldn't get you in trouble too. Anderson reports a 1966 incident when he asked a man named Dobbin (born in 1883) if he knew the lyrics to The Wild Colonial Boy. "I should hope not!" Dobbin angrily replied. "When I was a lad in Rockhampton anyone who sung that in a pub would be put in jail, even if they only tried to pick out the tune on the piano."
7) The Beechworth mail coach was robbed on May 24, 1859, by four men named Bergin, Hackett, Williams and Farrell.
8) We can't be certain the real Macoboy was ever robbed at all. "It was alleged that the real life Judge Macoboy was held up by a bushranger at Beechworth in about 1862," Victoria's Geelong College says. "Other than family anecdotes there is little evidence to support this event." True or not, the incident is now an indelible part of the song.
9) AT Hodgson's print shop, which gave us WCB's first printed lyrics in 1881, was based in Castlemaine, Victoria too. Presumably the song's local content made it particularly popular there.
10) Anderson makes passing mention of an unnamed Irish ballad about a Castlemaine-born man called Dan Duggan, who's transported to Australia and turns bushranger. He's clear that song has nothing to do with The Wild Colonial Boy, but I wonder of the Duggan surname may have leaked across nonetheless?
11) The Hancock's Half Hour radio episode is The Sleepless Night, first broadcast on June 3, 1958.
12) Bizarrely, Castlemaine in Australia makes no effort to claim The Wild Colonial Boy, despite the fact that its link to the song is far stronger than Ireland's. The city's Wikipedia page lists just two contributions it's made to popular culture: Castlemaine XXXX lager and an Aussie TV series called The Glitch.
13) The Wild Colonial Boys, by Granville Allen Mawer (Arcadia, 2004). A revised edition with additional material was published in 2016. Available from Australian Scholarly Publishing.
14) Jack was originally what The Oxford Names Companion calls "a pet form of John", used by friends and family to indicate affection. My guess is that the Dooling family adopted this habit, creating the first of many layers of confusion in how John's name was rendered by the authorities.
15) Mishearing the spoken "Dooling" as "Doolan" and writing it down that way must have been an easy mistake to make. Something similar happened to Tom Dula, who bureaucrats listed as "Tom Dooley" on his POW release papers in 1865. See my PlanetSlade essay on that song for more details.
16) The Castlemaine information, plus John's date of birth, seems to have been taken directly from William Dooling's notes in the family bible.
17) Bendigo Advertiser, January 17, 1872.
18) Jack's committal hearing came at Bendigo Police Court on January 16, 1872. Purely by coincidence, the real Judge Macoboy happened to be working elsewhere in the same building on that day. Macoboy never tried any case involving Jack, so this is the closest they came to meeting in real life.
19) The Independent's comments are quoted in the February 23, 1872, issue of a Melbourne paper called the Argus. I don't know the date of the paper they were taken from.
20) Ann's howl of grief in the courtroom finds a strange echo in Robert Hughes' 1986 book The Fatal Shore. Recalling the single most remarkable rendition of the Wild Colonial Boy he ever heard, Hughes says: "It was sung by a fat, seamed old Sydney prostitute, buoyed up by a few too many glasses of sweet port on the Woollomooloo docks late one night in 1958 - not in the rollicking front-room way of men, but the off-key dirge of a mother grieving for her dead son."
21) This time I've taken the Independent's words from their appearance in the Gippsland Times of February 27, 1872. It was then quite common for newspapers to quote editorial comment from titles elsewhere in the country.
22) The Argus, September 2, 1875. In the incident reported here, Jack was actually the victim of an assault by one of his fellow prisoners. John Sullivan, known as the Yarra Flats Bushranger, gave him "a severe blow on the head" with a mallet when some dispute arose between the two men. Sullivan "added many months to his long sentence" by doing this, the paper adds.
23) "It is a remarkable family history," Mawer writes. "All of the Dooling children had survived infancy but two had been killed in accidents and two others had fallen victim to disease before either of their parents died. Only the youngest, Annie, lived beyond the age of 51." The Bendigo Advertiser had seemed to prophesy all the tragedy to come in its January 16, 1872 story about the Dooling clan, where it spoke of the "strange fatality which follows the children of some families".
24) The information on Jack's life after prison comes from Mawer's book, but he credits it to family tree research by Joy Munns. Her great-great grandmother was Ann Dooling's sister, which makes Jack her first cousin three times removed.
25) Ned was released in 1885, having served 13 years of his 17-year sentence. He went on to marry, found work as a labourer on the railways and died at Richmond in 1923.