Once the darling of Australian political cartooning, Larry Pickering died at his Gold Coast home bankrupt and in pain, with his reputation tarnished by his own hand.
Pickering had been suffering from lung cancer for the past two years, and had recently been in hospital.
He checked himself out of hospital last Friday to spend his final days at his Gold Coast home with his family. He died on Monday night aged 76.
Close friend and fellow cartoonist Paul Zanetti said Pickering had remained positive and upbeat until the end, despite being in obvious pain.
"Larry had the most influence on my own life than anyone," Zanetti wrote.
"He was loyal, generous, entertaining and simply brilliant."
However, news of the notorious cartoonist's death was met with mixed response on social media.
Commentator Michael Pascoe called him a "conman and scumbag", others called him a racist and a misogynist.
Pickering was very popular in the 1970s and 80s, with his work for outlets including The Australian and The Sydney Morning Herald earning him four Walkley Awards.
His caricatures of prominent politicians of the day, including Gough Whitlam and Malcolm Fraser, were collected into bestselling books.
He also famously published a series of calendars in the 1980s featuring caricatures of politicians in the nude, which topped the bestsellers list.
His reputation as a larrikin who pushed the boundaries of free speech seemed secure following his retirement from full-time cartooning in 1981.
But Pickering returned to public life with the rise of then prime minister Julia Gillard.
Pickering depicted Ms Gillard naked and wielding sex toys in a series of cartoons that Ms Gillard herself described as "vile and sexist."
His attacks on Ms Gillard continued until his death.
Pickering published another naked caricature of her on his blog just last month, saying he was disappointed he hadn't been asked to paint her official portrait, which had just been unveiled.
He also courted controversy for his view on Muslims, which became publicly extreme following the terrorist attack on the Paris offices of magazine Charlie Hebdo in 2015.
Queensland police visited him to discuss his safety after he published a cartoon in response to the attacks showing the prophet Mohammed skewered like a pig on a pencil.
He infamously spoke at a far-right rally saying he hated Muslims, adding that not all Muslims were bad because "they do chuck pillow-biters off buildings".
Pickering lost most of his money in the 1987 stockmarket crash, and became an undisclosed bankrupt in 2010 when a betting software company he helped set up collapsed, taking millions of dollars in investors' money with it.
At the time of his death he was living on a pension and child support payments as well as income from his website.
He is survived by his wife and 11 children.
Australian Associated Press