Larry Flynt, founder of Hustler magazine and self-proclaimed "smut peddler who cares", has died aged 78.
Flynt died in his sleep at Cedars-Sinai Medical Center in Los Angeles with family by his side, according to his manager.
He frequently courted controversy and was subject to lawsuits during a career spanning five decades.
Flynt was shot in 1978 while standing outside a courthouse in Georgia during a trial for obscenity.
The assassination attempt left him a paraplegic. He had his wheelchair gold-plated and lined with velvet.
The man alleged to be the perpetrator was never charged. However he was executed years later, in 2013, in connection with a series of unrelated murders.
Born in Kentucky in 1942, Flynt was a school drop-out who began his career in the adult industry by launching strip clubs in Ohio along with his brother.
A newsletter about those clubs evolved into Hustler magazine, which was first published in 1974.
According to Flynt, at the height of circulation the publication was bought by about three million people a month.
His pioneering legal battles were depicted in the 1996 film The People vs Larry Flynt, in which he was played by Woody Harrelson.
One lawsuit in particular saw Flynt sued for a sexual parody cartoon of televangelist Jerry Falwell that appeared in Hustler in 1983.
The cartoon, a fake advert, showed Mr Falwell saying his first sexual encounter had been with his mother in an outhouse.
Mr Falwell sued Flynt for $50m (£36m) for libel and won in a lower court, but the case went up to the US Supreme Court.
Flynt then won the case with a unanimous 8-0 verdict, which reinforced free speech rights and protections for satire in the US.
His business empire extended into other areas of entertainment and was thought to have a $150m turnover at one point, according to Reuters.
Away from pornography, he launched and lost long-shot bids at political office and was married five times.
Minda Gowen, spokeswoman for Larry Flynt Publications, said Wednesday that he died from "from the recent onset of a sudden illness".
His brother told US media that the death was caused by heart failure.