After five years in breakfast radio, the comedian was keen to get back to the stage - with a tale that combines history, politics and a good dose of silliness.
"Burke and Wills is pretty much the perfect historical story of stupidity, because these two guys tried to walk from Melbourne to the top of Australia," said Sammy J.
The expedition set off from Melbourne in 1860, with Burke and Wills, along with fellow explorers John King and Charles Gray, becoming the first Europeans to cross Australia from south to north, arriving at the Gulf of Carpentaria in 1861.
But only John King survived, with the help of the Yandruwandha people, who receive little recognition in historical accounts of the expedition.
The Burke and Wills tale has long been mythologised as a story of courageous failure, perhaps best remembered for the "dig" tree at Cooper Creek, where supplies were left for the explorers before they perished.
While Sammy J attests the musical has been meticulously researched, some elements of his version are more accurate than others - such as Burke and Wills having a sideline in songwriting.
They also misread the engraving on the famous "dig" tree, thinking it said "gig" - an invitation to tell their story in song, even as they're starving to death.
The Burke and Wills expedition was funded in part by the Royal Society of Victoria, and its historic building on La Trobe St in Melbourne is actually where Sammy J wrote the show.
The comedian is used to tackling difficult subjects, but admits he was apprehensive writing about the role of First Nations people, taking on Noongar actor and writer Carissa Lee as cultural dramaturg.
The musical format works not only as a licence to laugh at Australia's colonial failures, but a way to talk about a history that is still very much being reckoned with.
"I've always used music in that way, where you can treat a really serious subject with a bit of lightness or melody," said Sammy J.
"It means that people pay more attention, they don't feel like they're being hit over the head."
The musical is currently a low-fi production in the tradition of the Melbourne Fringe, but Sammy J hopes it can be developed further, and in time find a bigger audience.
A bit like ... Hamilton? Never, says Sammy J. But when most musical theatre on local stages is imported, it's rare to see a home-grown story.
"We support musicals when they come out here, as we should, but I also think it's really important to tell our own stories," he said.
"This is a very Australian story that I'm excited about bringing to the stage."
Fiasco: A Burke and Wills musical runs October 8-19.
Melbourne Fringe Festival returns September 30 and runs until October 19.
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