AP Al Goldstein displays some of his reading material upon leaving the federal courthouse in Kansas City, Kan., where his obscenity trial resumed in 1977.

Al Goldstein, the bearded, bird-flipping publisher of Screw magazine who smashed down legal barriers against pornography and raged against politicians, organized religion and anything that even suggested good taste, died Thursday, according to a friend. He was 77.

Goldstein died at a Brooklyn hospice after a long illness, said the friend, attorney Charles C. DeStefano.

Of all the would-be successors to Hugh Hefner's sexual throne, no one was as out there as Goldstein. Whether publishing nude photographs of Jacqueline Kennedy, or placing an 11-foot-tall sculpture of an extended middle finger outside his Florida home, Goldstein was a one-man, uncensored army of boiling humor, manic attire, numerous divorces and X-rated visions of peace and love.

"To be angry is to be alive. I'm an angry Jew. I love it. Anger is better than love. I think it is more pure," he said in an interview in 2001. "There's so much to be angry about, because people are ripped off, the election went to the wrong person, the good guys usually lose and society sucks."

Mary Altaffer / AP file Screw magazine publisher Al Goldstein sits for an interview at a coffee shop in New York in 2003.

Goldstein backed up his attitude where it counted, with his wallet, spending millions of dollars on First Amendment lawsuits, hundreds of thousands running unsuccessfully for sheriff in Florida, and millions more in numerous divorce settlements.

DeStefano remembered Goldstein as an "intellectual who cared about the world and geopolitics." But after a lavish life of mind and body, Goldstein was often broke, and, he feared, harmless.

"I'm old hat," Goldstein told New York magazine in 2010. "I've become a senior citizen. I'm an old Jew."

Goldstein was born in Brooklyn, his childhood branded by a dirty world. He was a stutterer, a bed wetter and a chronic masturbator, and a target for bullies. Before founding Screw, he served in the Army; sold insurance; drove a car for the gossip columnist Walter Winchell; got himself jailed in Cuba for taking unauthorized pictures of Fidel Castro's brother, Raul; and, as a photographer for Pakistan International Airlines, was on hand in 1962 when Kennedy (then the first lady) visited Pakistan.

In his spare time, he watched pornography.

When he and Jim Buckley chipped in $175 apiece and co-founded Screw, in 1968, the sexual revolution was on and the American legal system was caught up in a battle over obscenity. Goldstein's initial cause was himself, to have the right to publish the kinds of materials he liked to look at.

"Screw grew from a combination of many factors, chief of which was my own dissatisfaction with the sex literature of 1968 and my yearning for a publication that reflected my sexual appetites," he wrote in a 1971 Screw anthology.

But Goldstein also felt that the cultural and religious establishment had convinced his generation that sex was wrong and turned them into "a lot of embarrassed people who bought nudie magazines on the sly."

The porn magazine's scathing, scatological editorials targeted church and state for justifying war while imprisoning erotic magazine publishers. Screw sold 140,000 copies a week at its height.

"I may be making a lot of money, but I really believe I'm doing some good by demythologizing a lot about sexuality," he told Playboy in 1974.

But the law was never far away. During the magazine's first three years, Goldstein was arrested 19 times on obscenity charges. Spending millions to defend himself, he ultimately scored a major victory in 1974 when a federal judge threw out an obscenity case brought against him.

After that, the willingness of the government to prosecute such cases waned, ending a period that saw books such as D.H. Lawrence's "Lady Chatterly's Lover" and Henry Miller's "Tropic of Cancer" banned and kept erotic publications under the counter.

But victory left Goldstein with the most dreaded of emotions — boredom.

"I really need the attention of being arrested, because that means I'm still bugging the establishment, that I'm still gadfly to the state," he told Playboy. "Acceptance of me and Screw would be the kiss of death."

Screw was eventually outporned by Larry Flynt's Hustler magazine and other ultra-explicit publications. Goldstein sought other outlets, and in 1974 launched a cable porn show, "Midnight Blue," which ran for nearly 30 years.

But as Screw faded, Goldstein became depressed and angrier, a danger to himself and to others.

In 2002, he was sentenced after a wild trial to 60 days in jail for harassing a former secretary with threatening phone calls and editorials. The conviction was later overturned when an appeals court ruled prosecutors had used overly inflammatory language at trial. A year later, Goldstein pleaded guilty to harassing one of his four ex-wives with obscene phone messages. He also accused his son, Jordan, of stealing hundreds of thousands of dollars' worth of watches from him.

"My son made me a broken man," he said.

In late 2003, the magazine folded and Goldstein filed for bankruptcy protection. On the upside, he lost 150 pounds following stomach stapling surgery the same year and married his fifth wife, a woman 40 years his junior. Things fell so far, though, that he was forced, at times, to sleep in a car and live in a Florida homeless shelter.

"Up until a month ago he still had that spark," said DeStefano. "In fact, he gave me the middle finger. As he did it, he smiled at me. I knew he was still Al Goldstein inside this shell of a body."

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Associated Press writer Kiley Armstrong in New York and former AP writers Larry McShane and Lukas I. Alpert contributed.