Dana Fradon contributed nearly 1,400 cartoons to the New Yorker, helping define its brand of satirical, wry and sometimes ridiculous humor in a magazine career that stretched from the Harry S. Truman administration into the George W. Bush years. “Under the Freedom of Information Act,” a pajama-clad character says in one of his drawings, looking skyward in prayer, “I’m requesting that you disclose what you have on me in your files.”

Mixing droll gags with acerbic satire, Mr. Fradon skewered plutocrats, hucksters, crass politicians, corporate honchos and a sensationalist media. In one cartoon, a broadcaster intones: “Those are the headlines, and we’ll be back in a moment to blow them out of proportion.”

Mr. Fradon, who once insisted he was less a cartoonist than a “misplaced baseball player,” generated ideas from radio, television and especially the New York Times, which he marked up with a pen over his morning coffee. The results were contemporary but also timeless, in part because corruption, greed and outright lies never seemed to go out of fashion.

One of his best-known cartoons depicted a set of file cabinets with labels reading, “Our Facts,” “Their Facts,” “Neutral Facts,” “Disputable Facts,” “Absolute Facts,” “Bare Facts,” “Unsubstantiated Facts” and “Indisputable Facts.” That drawing ran in 1977, former New Yorker cartoon editor Bob Mankoff noted in an interview, but “come on, what cartoon could be more relevant to what we’re going through now?” Perhaps the only thing missing was a drawer labeled “Alternative Facts.”

Mr. Fradon, who also wrote children’s books and contributed cartoons to newspapers across the country, was 97 when he died Oct. 3 at his home in Woodstock, N.Y. The cause was liver cancer, said his daughter, Amy Fradon, a folk singer.

The New Yorker featured cartoons beginning with its first issue, in 1925, and had already established itself as a leading platform for humorists by the time Mr. Fradon signed on in 1948 as the last cartoonist hired by founding editor Harold Ross. He went on to spend most of the next 55 years at the magazine, briefly leaving in the 1990s — he was reportedly frustrated by the new regime of editor Tina Brown — before returning under current editor David Remnick.

Mr. Fradon was “one of the bedrock cartoonists” of the magazine’s mid-century “Golden Age,” fellow New Yorker cartoonist Michael Maslin said by email. Along with artists such as Whitney Darrow Jr., Frank Modell, James Stevenson and Robert Weber, he added, Mr. Fradon was “unbelievably adept at providing high-bar work — much of it evergreen — seemingly at a headline’s notice.”

“As a fledgling artist, I paid attention to the breadth of his curiosity as well as the mastery of his drawings — the structured washes and tones and the animated line,” Edward Koren, another New Yorker cartoonist, wrote in a tribute for the magazine. “This is what Fradon used to satisfy the signature requirement of [the] magazine’s first art editor, James Geraghty, who asked of his artists, ‘Make it beautiful.’ ”

Mr. Fradon’s “elaborate drawings,” he continued, “were generous masterpieces of compressed fun.”

One such cartoon, from 1991, showed a couple standing in the moonlight on a remote jungle hilltop, watching as a volcano erupted like a jack-in-the-box, spouting a spring-loaded toy head instead of molten lava. “The gods are antic tonight,” the caption read.

Much of his work was more overtly satirical, addressing current affairs without dipping into partisan politics — albeit with an unmistakably left-leaning point of view. A self-described Roosevelt Democrat, he served for several years in the 1970s on the city council in Newtown, Conn., before deciding that issues of underground utility wires were taking too much time away from drawing.

One Fradon cartoon featured a pair of grumpy middle-aged men sneering at a bird feeder, marked “Squirrels Welcome.” It was accompanied by a one-word caption: “Liberals!” Another showed an angry invalid, tended to by a doctor. “You should take it easy for a while, Mr. Harner,” the physician says. “You’ve been infected by the virus of hate.”

Mr. Fradon’s work drew on Greek mythology, Roman history, medieval lore and French literature, with one 1986 cartoon portraying what appeared to be the Three Musketeers, lifting their swords in unison and declaring, “Every man for himself!” Others ventured into the arcana of finance, showing a bank teller punching a customer in the jaw as part of “an extra ‘substantial penalty’ for the early withdrawal of your time deposit.”

“What motivates one cartoonist to do amusing drawings about cats, dogs, husbands and wives, and another to delve into bribes, kickbacks and political hacks?” Mr. Fradon asked in the preface of his 1978 collection “Insincerely Yours.” His former editor, Geraghty, offered one potential explanation: “Let’s face it, Dana, you’re not motivated by any love for the oppressed, you’re motivated by hatred of the oppressor!”

"Taken with a grain of salt, or salt substitute," Mr. Fradon wrote in his book, "it was a correct analysis."

It was also, perhaps, the result of an upbringing in Depression-era Chicago, where he was born Arthur Dana Fradon on April 14, 1922. His parents were Russian-Ukrainian immigrants who credited President Franklin D. Roosevelt’s New Deal with helping them through the Depression, and his father served as a precinct captain in their South Side neighborhood.

Mr. Fradon was raised in part by an older sister, Marion, and developed an interest in art and politics at a young age. He attended the School of the Art Institute of Chicago before being drafted into the Army, and rarely spoke of his war years aside from noting that by then he was already drawing political cartoons.

Moving to New York, he studied at the Art Students League, “a future cartoonists paradise” where attendance wasn’t taken and grades weren’t given, and where he met Ramona Dom, a fine arts student he married in 1948. She later became a celebrated illustrator, drawing Aquaman and Brenda Starr comics.

“Both my mom and dad were so busy drawing that they would put a big sheet of paper on the floor and drop colored pencils down for me to scribble with,” Amy Fradon told the New York Times in 2000, recalling her childhood. Mr. Fradon and his wife divorced in the early 1980s but remained friends, and in the past four years lived together with Amy and her husband, Peter Schoenberger. No other immediate family members survive.

Mr. Fradon contributed to publications including Collier’s, the Saturday Evening Post and the left-wing New Masses before being pointed toward the New Yorker by his brother-in-law, Albert Hubbell, a writer and illustrator at the magazine. He later wrote and illustrated several children’s books inspired by his love of the Middle Ages, including “Sir Dana: A Knight, as Told by His Trusty Armor” (1988).

Notable deaths in 2019: Elijah Cummings, Cokie Roberts, Toni Morrison and others we have lost this year

Don Imus | Don Imus, who spent more than half a century in radio and television skating along the edge of propriety and occasionally falling into the abyss of the unacceptable, died Dec. 27 at a hospital in College Station, Tex. He was 79. In a roller-coaster career in which he grew chummy with prominent politicians, repeatedly got suspended or fired for offensive cracks, abused drugs and touted health foods, Mr. Imus won a loyal following, made millions and transformed himself from a bad-boy DJ into a host whose program became a nearly mandatory stop for presidential candidates. Read the obituary (Richard Drew/AP)

For decades, he worked out of a pre-Revolution farmhouse in Newtown, where his attic studio was cluttered with drawings and artists’ materials, including his daughter’s coveted plastic farm animals, which he arranged on a wooden beam for inspiration. When the toys didn’t help, he enlisted his wife to help with animal drawings, especially of horses.

The couple collaborated again in recent years, working on cartoons they published on Facebook. One showed the grim reaper at a man’s apartment door, with a scythe in hand and “Trump” campaign button on his cloak. “Relax!” the caption reads. “I’m only here to spread fear.”

Mr. Fradon said that he was unable to stop drawing, long after filing his last New Yorker cartoon in 2003. “For a time, when I thought of a good idea that I thought would go in today’s New Yorker, I stifled it,” he told Maslin in a 2013 interview. “And then I said to myself: well don’t do that anymore, write ’em down — so I write them down on a scrap of paper and throw them into a pile.”