Controversial cartoonist Larry Pickering has died following a long illness.

Pickering’s death, aged 76, was reported by News Corp publications on Tuesday. Cartooning colleague Paul Zanetti also posted a condolence note to Twitter.

Pickering, who had suffered from cancer for some years, checked himself out of hospital on Friday.

“Things have reached a point where even Larry has to admit that his race is almost run,” his friend Harry Richardson wrote on the Gold Coast cartoonist’s The Pickering Post blog.

“He has lost a lot of weight and his condition has spread to his liver. He is now in considerable pain but is refusing pain killers as he intends to remain conscious and lucid for what time he has left with his loved ones.

“My thoughts and prayers are with Larry and his loving wife and children, who he adores.”

On Tuesday, The Australian – where Pickering worked for many years – described him as a trailblazer who paved the way for a new generation of political cartoonists.

A four-time Walkley award winner, he had a successful yet contentious career drawing for newspapers and books. He was also famous for political calendars, featuring caricatures of naked politicians, in the 1980s.

But he was also no stranger to controversy. He famously came out of retirement to wage a vitriolic campaign against Julia Gillard when she was prime minister. Ms Gillard responded by referring to The Pickering Post as “vile and sexist”, and called Pickering a misogynist.

Last year, the cartoonist gave a speech to the far-right Q Society slamming Muslims.

“I can’t stand Muslims,” he told the audience. “If they are in the same street as me, I start shaking.”

In January 2017, he was placed under protective police surveillance after posting a cartoon showing the Muslim prophet Muhammad on a spit roast, skewered on a pencil. That followed the Paris terror attacks on the Charlie Hebdo office.

As well as Islam and Muslims, Pickering’s other favourite targets included Aborigines and women.

The New Daily contributing editor Michael Pascoe was not among his fans.

“Pickering is commonly known as a cartoonist, but he’s also an inveterate liar, a bankrupt conman with a seedy history of fleecing the gullible of millions of dollars while not paying his own bills,” he wrote in 2012 for Fairfax Media.

Pickering lost millions of dollars in the 1987 sharemarket crash and was declared an undischarged bankrupt in 2010 after becoming involved in a betting software company that failed.

He apparently spent his last years relying on a pension and child support payments, as well as income from The Pickering Post. He is survived by his wife and 11 children.