Since the 1990s, Friedman has provided caricature illustrations for mainstream publications. However, he first attracted public attention in the 1980s producing morbid
alternative comics stories, sometimes working solo, sometimes with his brother
Josh Alan Friedman scripting the panels. These stories portrayed celebrities and character actors of yesteryear in seedy, absurd, tragi-comic situations. The brothers also wrote stories about
talk-show host
Joe Franklin, including one strip, written by Drew, for
Heavy Metal, "The Incredible Shrinking Joe Franklin", that prompted Franklin to sue the artist for $40 million. The suit was later dismissed. Novelist
Kurt Vonnegut Jr. compared his work to
Goya's. The Friedman brothers were first published in
RAW Magazine. Working with and without his brother, Drew's comics were published in
Heavy Metal,
Weirdo,
High Times,
National Lampoon and other comics anthologies from the 1980s into the early 1990s. The brothers published two collections,
Any Similarity to Persons Living or Dead is Purely Coincidental and
Warts and All. In a
Comics Journal interview, Drew Friedman lamented that he and his brother had failed to earn a living creating work that was time- and labor-intensive yet earned little. Josh gave up comics to become a journalist and a musician. Beginning in 1986, Drew illustrated a monthly feature, "Private Lives of Public Figures," for
Spy; these illustrations were compiled in a book published by
St. Martin's Press in 1992. He also provided illustrations for
Howard Stern's two best-selling books,
Private Parts and
Miss America. Friedman served as comics editor for the
National Lampoon in 1991, introducing the works of
Daniel Clowes and
Chris Ware to a wider audience. Since 1994, he has provided regular front-page illustrations for
The New York Observer. In 2006, Friedman published
Old Jewish Comedians (
Fantagraphics Books), a collection of portraits of famous and forgotten Jewish comics of film and TV in their old age, about which
Steven Heller, in
The New York Times Book Review, wrote: "A festival of drawing virtuosity and fabulous craggy faces... Friedman might very well be the Vermeer of the Borscht Belt." A sequel,
More Old Jewish Comedians (Fantagraphics Books), was published in 2008. A collection of newer work,
The Fun Never Stops! was published by Fantagraphics in 2007. Describing his illustration style in 2017, Friedman said it might not appeal to "people who find warts, pimples, wrinkles, flop-sweat, jowls, boils, rosacea, nose hairs, ear hairs, drool, baggy eyes, gin blossoms, moles, liver spots, neck waddles, nasal labia folds, crinkles, furrows, creases, puss, pustules, bumps, lumps, yellowing and/or rotting teeth, missing teeth, gums, dentures, saliva, double chins, triple chins, blotches, scars, lumps, zits, five o'clock shadows, folds, bulbous noses, craters, chapped lips, man-boobs, goiters, pock marks, whiteheads, blackheads, rashes, nose leakages, emasculations, calluses, scabs, balding/bald heads, nodules, freckles, protuberances, welts, carbuncles, papules, festers, and
Shemp distasteful," adding, "Liver spots are my
Ninas." While continuing to accept commercial assignments, Friedman began working as a portrait fine artist. "It helps if I'm passionate about the subject I'm drawing," he said in a 2015 interview. "As I get older I have less patience to draw someone or something I have no connection to or don't really like, or hate, even a politician. I just don't like the idea of staring into the face of someone I detest for several days drawing him or her. It's unsettling." Friedman was one of the artists photographed in his studio for
The Artist Within: Book 2: Behind the Lines by photographer
Greg Preston, published in 2017. Friedman's portrait of
Barack Obama appeared on the cover of the
New Yorker on January, 26, 2009. Friedman's 2019 book
All The Presidents featured portraits of 45 United States presidents. Friedman is the subject of the 2024 documentary film
Drew Friedman: Vermeer of the Borscht Belt. == Education ==