Publishing millionaire and 60s radical Felix Dennis has died aged 67, after a "long and painful" battle with throat cancer.
The businessman first found fame as one of the founders of 60s counterculture magazine Oz, which was caught up in a high-profile obscenity trial in 1971.
He went on to found Dennis Publishing, which published titles like The Week, Your Spectrum and men's magazine Maxim.
His office said Dennis died on Sunday, "surrounded by his loved ones".
"After a long and painful battle with cancer, Felix died peacefully at his home in Dorsington [in Warwickshire], aged 67," continued the statement.
"Felix was a publishing legend, famed for his maverick and entrepreneurial style and, more lately, a successful and much-loved poet. He will be greatly missed."
"Thank you for the support and kindness of those who share our feelings for Felix, and we ask that you respect our privacy during our time of grief."
Born in Kingston-upon-Thames, in Surrey, Dennis played in a number of R&B bands as a teenager before briefly attending Harrow College of Art.
His tenure lasted little more than a term, though, before he moved out of home and began creating window displays for department stores to make a living.
He was first hired by Oz in 1967, creating a poster to mark Che Guevara's death for the magazine's eighth issue. Famously, he spelled the Marxist revolutionary's name wrong - a mistake which occurred, he said, after checking it in The Guardian.
By 1969, he was a full-time writer and co-editor on the establishment-baiting magazine - and caused shockwaves when he invaded the stage on David Frost's television show, uttered a four-letter swear word and squirted the host with a water pistol.
Dennis was briefly jailed in 1971 after an obscenity trial relating to a "schoolkids' edition" of Oz.
About 20 secondary school pupils had been handed the reins of the magazine, and they portrayed cartoon character Rupert the Bear as semi-naked with genitals on display.
The magazine was raided by the Obscene Publications Squad and its owners were charged with "conspiracy to corrupt public morals".
The case became a cause celebre for the hippy counter-culture and on release from jail, Dennis was whisked away from the press by none other than Beatle John Lennon.
Following his acquittal from the court of appeal in 1973, Dennis went on to found his own publishing company, launching with Kung-Fu Monthly.
Conceived as a quick cash-in to capitalise on the popularity of film star Bruce Lee, it ran for years.
Many of his other titles appealed to specialist interests - including Auto Express, Mac User and Computer Shopper. He also published one-off magazines to coincide with Hollywood's growing blockbuster industry - signing deals for Star Wars and Jaws, among others.
Today, Dennis Publishing is responsible for more than 50 magazines, websites and mobile sites, including The Week, Men's Fitness, PC Pro, Octane and Viz.
Its biggest publication is currently The Week, a digest of global current affairs, which has a circulation of almost 200,000 per week.
In 2007, he made £144.5 million by selling off all 31 international editions of Maxim, when it was the best-selling men's magazine in the world.
He also made millions from co-founding US computer mail order company MicroWarehouse, which floated on the stock market in 1992.
In total, Dennis was worth about £500m. He claimed to have spent as much as £100 million of that on "sex, drugs and rock 'n' roll" - a lifestyle that culminated in a crack-cocaine addiction in the 1990s.
"It was complete madness," he told the BBC in 2006. "I'm very embarrassed about it. I had a wonderful time, I'm not going to lie, but I shouldn't have done it. It was fun at the beginning, but then it becomes not so pleasant.
"You're behaving badly and there's no one to tell you to stop, it gets out of hand. And then you get addicted. So I walked away."
In 1999, he was treated for a serious thyroid condition, and took advantage of a stay in hospital to write his first poem, on a post-it note.
"I needed something utterly absorbing and gripping, when I wasn't doing business," he said, "and I certainly found it.
"When you're writing, you're in a totally different zone... I can start a difficult poem and look up at the clock and see to my astonishment that three hours have passed.
"Instead of taking crack cocaine, going out with whores and boozing, I'll sit down alone in a room and have just as much fun, if not more."
He penned more than 1,500 poems, including one about his charity, The Heart of England Forest, which aims to create a large forest of British broadleaf trees in Warwickshire. "Whosoever plants a tree / Winks at immortality," he wrote.
It was not his only charitable endeavour. Earlier this year, Dennis brokered a deal which gave all 12,500 schoolchildren in St Vincent and the Grenadines a laptop.
The publisher's relationship with the Caribbean nation began in the 1990s when he bought Mandalay, David Bowie's hilltop villa on the exclusive island of Mustique.
He would often appear at the island's blues festival, revisiting the R&B riffs of his youth.
His other interests, according to his personal website, included "commissioning bronze sculpture, drinking French wine and avoiding business meetings".