Singer, songwriter, satirist and novelist Kinky Friedman, who led the alt-country band Texas Jewboys, toured with Bob Dylan, sang with Willie Nelson, and dabbled in politics with campaigns for Texas governor and other statewide offices, has died.

Friedman, 79, died Thursday at his family’s Texas ranch near San Antonio, close friend Kent Perkins told The Associated Press. Friedman had suffered from Parkinson’s disease for several years, Perkins said.

“He died peacefully. He smoked a cigar, went to bed and never woke up,” said Perkins, who was working as an actor when he met Friedman at a party 50 years ago when both were signed to Columbia records and movie contracts.

“We were the only two people with tuxedos and cowboys hats. Two Texans gravitating toward each other,” Perkins said. “He was the last free person on earth … He had an irreverence about him. He was a fearless writer.”

In the 1970s, his satirical country band Kinky Friedman and the Texas Jewboys wrote songs with titles such as “They Ain’t Makin’ Jews Like Jesus Anymore” and “Get Your Biscuits in the Oven and Your Buns in Bed.” Friedman joined part of Bob Dylan’s Rolling Thunder Revue tour in 1976.

By the 1980s, Friedman was writing crime novels that often included a version of himself, and he wrote a column for Texas Monthly magazine in the 2000s.

Friedman’s run at politics brought his brand of irreverence to the serious world of public policy. In 2006, Friedman ran for governor as an independent in a five-way race that included incumbent Republican Rick Perry. Friedman launched his campaign against the backdrop of the Alamo.

“We’re gypsies on a pirate ship, and we’re setting sail for the Governor’s Mansion,” Friedman said at the campaign launch. “I’m calling for the unconditional surrender of Rick Perry.”

Some saw the campaign as another Friedman joke, but he insisted it was serious. His platform called for legalizing medical marijuana, boosting public education spending through casino gambling and supported same-sex marriage. Campaign slogans included “How Hard Could It Be?” and “He ain’t Kinky, he’s my Governor.”

“Humor is what I use to attack the windmills of politics as usual,” Friedman said.

Perry won re-election in 2006, and Friedman finished last. He did not give up politics, however, and unsuccessfully ran for state agriculture commissioner as a Democrat in 2010 and 2014.

Born in Chicago, Richard Samet Friedman grew up in Texas. The family’s Echo Hill ranch where Friedman died ran a camp for children of parents killed serving in the military.

Funeral services were pending, Perkins said.