Brad Holland, an idiosyncratic artist who upended American illustration in the 1970s with his startling imagery for Playboy magazine and The New York Times’s opinion page, spawning a generation of imitators, died on March 27 in Manhattan. He was 81.
His brother, Thomas Holland, said he died in a hospital from complications of heart surgery.
Mr. Holland was in his late 20s and contributing to Playboy and a few of New York City’s underground papers, including The New York Review of Sex and Politics and The East Village Other, when he was invited to be part of an experiment at The New York Times.
In 1970, the paper had introduced what it called an Op-Ed page — the name referred to its placement opposite the editorial page — as a forum for essays and ideas. The art director of this new page, Jean-Claude Suares, was another veteran of the underground presses; while working at The Times, he was also designing Screw magazine.
For The Times, Mr. Suares wanted to commission standout art to accompany the writing, but he didn’t want to illustrate the themes of the articles literally. He was an admirer of Mr. Holland’s work and recruited him, along with other notable insurgents, including Ralph Steadman, the British caricaturist who had been illustrating Hunter Thompson’s gonzo adventures, and a coterie of European political cartoonists.
Mr. Holland had already attracted attention with the gorgeous rococo images he made to illustrate Playboy’s “Ribald Classics,” a series that reprinted erotic stories by the likes of Ovid, Jonathan Swift and Mark Twain. His work could be surreal, grotesque and beautiful, and it was often inscrutable. It recalled the satirical engravings of the 19th-century caricaturist Thomas Nast and the more terrifying paintings of Francisco Goya.
He continued in the same vein for The Times. He produced a dark cloud of weeping faces, their tears falling on a raging fire, to illustrate an essay about welfare. Another image — of a fearsome figure with a belt cinched around his upper arm, pulling it tight with his teeth and brandishing a spoon at the gaping mouths sprouting from the skin below (to accompany another article on welfare) — was rejected, but ran later with an essay by a heroin addict. As the Watergate scandal unfurled, he rendered President Richard M. Nixon in myriad ways: atop a teetering stack of faceless, stumbling underlings, his coattails aloft, for instance, and as a grim collection of heads resembling the statues on Easter Island.
In 1976, the paper nominated Mr. Holland for a Pulitzer Prize.
“All the Art That’s Fit to Befuddle” read the headline of a 1977 New York magazine article by Michael R. Gordon about the upstart Op-Ed page, naming Mr. Holland as an avatar of the new form. Mr. Gordon pointed out that the work Mr. Suares chose not only pushed the boundaries of political cartoons but was also weird and abstract enough to satisfy a key Times mandate: that the artwork not express any overtly political point of view.
Political cartoonists carped that as a result, as Pat Oliphant, then at The Washington Star, put it, the Op-Ed art was “the sort of cop-out you can expect from a paper of record that wants to use art but doesn’t want comment.”
That view was not widely shared. If some readers were befuddled by Mr. Holland’s strange and magical imagery, graphic artists were entranced.
By the 1980s, his work seemed to be everywhere — in every major magazine, on political and theater posters, in advertisements for corporations and institutions like IBM and the MacArthur Foundation, on book and album covers.
For Stevie Ray Vaughan’s debut album, “Texas Flood” (1983), he painted Mr. Vaughan as suave and shadowed.
When Time magazine declared the Ayatollah Khomeini “Man of the Year” in January 1980, it was Mr. Holland’s stern portrait that glared from the cover. (The issue was published just a few months into the hostage crisis, which would last 444 days, and many readers reacted by canceling their subscriptions.) Mr. Holland would go on to illustrate several more Time covers, creating portraits of Zbigniew Brzezinski and Jimmy Carter among others.
In “9½ Weeks,” the erotic 1986 film starring Kim Basinger and Mickey Rourke, a slide show of Mr. Holland’s paintings provided the engine for one steamy scene.
A self-taught polymath, Mr. Holland did not take kindly to direction. He worked constantly on his own ideas, which he said sprang from his unconscious, or from characters he saw on the street, or from some philosophical concept he was trying to puzzle through. It was his habit to offer his portfolio to art directors to see if what he was making might match something they had in the works.
“It wasn’t a surefire method,” Steven Heller, who followed Mr. Suares as art director of The Times’s Op-Ed page, said in an interview. “It worked maybe 50 percent of the time. But what he did was establish a protocol for illustration so illustrators didn’t have to mimic what was on the page.”
In 2005, Mr. Holland was inducted into the Society of Illustrators Hall of Fame.
His marriage to Judy Pedersen in 1980 ended in divorce. His brother is his only immediate survivor.
Bradford Wayne Holland was born on Oct. 16, 1943, in Fremont, Ohio, the eldest of four sons of Pierce Holland, a house builder, and Mary Ellen (Fick) Holland.
He was determined to be an artist, although Fremont offered neither role models nor art supply stores. So he improvised.
He bought airplane model kits, threw out the parts and used the paint and brushes, with shirt cardboards as canvases. He read about charcoal drawings in how-to-draw books he checked out from the library, and he soaked charcoal briquettes in lighter fluid and tried to make drawings that way. At 15, he packed all of his drawings into a box and sent them off to Walt Disney Productions. A year later, the box was returned, much battered, with a rejection letter from Mickey Mouse.
After high school, he moved to Chicago, where he swept floors in a tattoo parlor before finding a job doing paste-up work for a catalog company. The larger, more established studios, he later recalled, did not take to his eccentric work, responding with blank stares and, in one instance, suggesting religious counseling.
He spent a few years in Kansas City, Mo., illustrating picture books for Hallmark. (His managers there told him his drawings weren’t friendly enough.) Once he had saved $1,000, he headed for Manhattan.
It was Playboy, however, that changed his life. After visiting the magazine’s offices in Chicago in late 1967 and leaving his portfolio for Arthur Paul, Playboy’s celebrated art director — and the creator of the bunny logo — he turned down the assignment that followed.
“I’m sorry,” he told the assistant who phoned him. “I only do my own ideas.”
A few days later, he got a call from Mr. Paul himself, urging him to reconsider. But Mr. Holland was adamant.
“I don’t know if my ideas would be any better,” Mr. Holland told him. “But I know they’d be more personal.”
Mr. Paul relented, and Mr. Holland worked for Playboy for the next quarter-century.
“In conventional professional terms, everything I said and did during those three days was wrong,” Mr. Holland wrote on his blog in 2018. “But God bless Art Paul, I had done them with the right guy. I had stumbled up the stairs in the dark, and when the lights came on, there I was.”