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A Pinellas cartoonist was jailed for obscenity 26 years ago. He just got off probation.

Largo artist Michael Diana served three days in jail for his infamous “Boiled Angel” comics. He moved to New York and kept making art, but in Pinellas County he was still a wanted man.
In this March 22, 1994 photo, artist Michael Diana, right, sits in court as his attorneys discuss jury selection in his obscenity trial. Diana became the first cartoonist in U.S. history to be jailed for obscenity.
In this March 22, 1994 photo, artist Michael Diana, right, sits in court as his attorneys discuss jury selection in his obscenity trial. Diana became the first cartoonist in U.S. history to be jailed for obscenity. [ RIVENBARK, MAURICE | Tampa Bay Times ]
Published Feb. 6, 2020|Updated Feb. 6, 2020

In 1994, a jury convicted Michael Diana of distributing hand-drawn comic books that they called legally obscene. A Pinellas County judge sent the skinny convenience store clerk from Largo to spend the weekend in custody while pondering his sentence, then put him on probation for three years.

Those three days behind bars made Diana the first cartoonist in U.S. history to be jailed for obscenity. The notoriety led to him to display his paintings at the Museum of Modern Art and speaking engagements in Berlin and Amsterdam. He even had his private parts cast in plaster by a rock groupie who did the same to Jimi Hendrix.

In the meantime, he moved to New York and failed to obey the terms of his probation. In 1998 he was classified as a violator and a warrant went out for his arrest.

Michael Diana.
Michael Diana. [ Courtesy of Michael Diana ]

Now, 26 years later, Diana’s attorney, Luke Lirot, said Wednesday that his client has finally completed probation.

Diana, now 50, is still an artist but no longer a wanted man.

Related: First Amendment attorney Luke Lirot recounts local strip club history

Diana told the Tampa Bay Times he’s relieved. Every time he flies back to New York from another country, he said, he is held up by Homeland Security because of his outstanding warrant. They usually turn him loose upon learning Pinellas authorities won’t extradite him over a misdemeanor charge.

He’s continued painting and drawing the same things that originally got him in trouble, he said, but now the rest of the world has seemingly caught up. These days he sees Adult Swim shows on the Cartoon Network or images in video games that aren’t that different from his 1990s work.

“Everything seems more open now,” he said.

Law enforcement first stumbled across his comics, which he published under the name “Boiled Angel,” as part of the investigation into the “Gainesville Ripper” slayings. Although serial killer Danny Rolling confessed to those crimes in 1990, the comics drawn by the pasty-faced Diana were viewed by police as so disturbing that they feared they might be a preview of his future massacres.

Diana said his ugly drawings of rape, murder, dismemberment, satanic rituals and child abuse were inspired by real-life news accounts, that they were intended to hold a mirror up to modern times.

At his 1994 trial, Lirot brought in experts from San Francisco and New York to attest to the artistic value of Diana’s drawings. Prosecutors told the jury that Pinellas County “doesn’t have to accept what is acceptable in the bathhouses in San Francisco, and it doesn’t have to accept what is acceptable in the crack alleys of New York.”

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The jury took just 90 minutes to find him guilty of three counts of obscenity. When Judge Walter Fullerton sent him to the slammer for the weekend, other inmates asked what he was in for.

“For drawing cartoons,” Diana said.

“Damn, they’ll throw you in here for anything!” one inmate replied.

Fullerton sentenced him to three years of probation, a $3,000 fine and 1,000 hours of community service. The judge also told him to take a journalism ethics course, get a psychological exam, draw nothing obscene and stay away from minors.

On appeal, one of the counts against him was thrown out — it involved a comic book he hadn’t even drawn yet — but the other two were upheld. His case went to the U.S. Supreme Court, which refused to hear it.

With the appeals and the move to New York, Diana said he lost track of which probation terms he’d completed and which were left. However, he’s now the subject of a forthcoming documentary called “Boiled Angels.” He said the film prompted him finally to resolve his case.

Meanwhile he’s still got copies of his officially obscene comic books for sale. Younger customers don’t see why they were controversial, he said. For some older buyers, he said, “they’re a collector’s item.”


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