When a Professor Trades the Academy for an Art Career of His

When New York City went into lockdown in the spring of 2020, Thomas Woodruff started sketching dinosaurs. Not as a child might doodle a T. rex, but as an artist drawing a self-portrait. At 62, he was 20 years into his career as the head of the illustration and cartooning departments at the School of Visual Arts, and he’d begun to worry that he and his students came from different eras. One class failed to recognize Picasso’s “Guernica” but could name Forky, the Picasso-inspired spork character in Toy Story 4. “It doesn’t count anymore if you’re a gay man of a certain age who went through the AIDS crisis,” he says from the same drafting table in his studio, a repurposed barn in Germantown, N.Y., where for more than a year he taught via Zoom. “It’s something that’s just kind of like, ‘Well, you’re a dinosaur.’”

Woodruff doesn’t look like a washed-up member of the old guard. In fact, on a sunny Saturday afternoon in April, he bounces merrily around his work space in gold-and-zebra-print VaporMax Gliese Nikes and a plaid tracksuit, his silvery hair styled into a psychobilly quiff. The graphic novel he spent the better part of a decade laboring over, a 300-page hand-drawn masterpiece of the form titled “Francis Rothbart!: The Tale of a Fastidious Feral,” is coming out in the fall. And he’s changed his life: Like his peers in the Great Resignation, he quit his job. “I just couldn’t do it anymore,” he says. “I had to be a bad guy when I was a chair because I had to be an authority figure, but the truth is, I can burst into tears at a moment’s notice because of, you know. …” He trails off, reminded, as he has been often during this pandemic, of the loved ones he lost to AIDS.

His home upstate is a memorial to his late friends: There are names inscribed on paving stones in the yard; a credenza by his former assistant, the queer artist Shawn Peterson, who died in 2016 at the age of 49, stands at the top of the stairs leading into his studio; and a framed photo of Woodruff’s friend Frank Moore, inventor of the AIDS ribbon, hangs over the radio that plays the local classical station while he works. Even a recent renovation was possible only after Woodruff sold “Apple Canon” (1996), which comprises 365 paintings of apples that riff on the aphorism “An apple a day keeps the doctor away.” Woodruff made the series in response to a question he found himself asking every day: Why was he still alive?

Like plenty of other teachers, Woodruff is haunted by the questions he has found himself asking his students — queries that play in his head as he works. But he may just be the first one to see his career take off in retirement, as the darkness lurking under the hokey surface of his paintings meets our new, dark time. When he opened his show at Vito Schnabel Gallery in New York in March, each cheeky, rainbow-stuffed painting of a dinosaur included at least one asteroid. “I was thinking of the moment of extinction and trying to ask, ‘How do you go through the annihilation with some kind of grace and acceptance?’” he says. One answer can be found in Woodruff’s “Benedict” (2022), in which a T. rex appears as a saint rapt in spiritual ecstasy. And then there’s “Martha” (2021), a pterodactyl modeled after the choreographer Martha Graham that claws at her chest — Woodruff’s take on the Catholic parable of the pelican who pierces herself to feed her young. “She’s kind of like the mother who has no children,” he says. “Just as the asteroid strikes.”

Credit…Bill Cunningham/The New York Times

WOODRUFF HAS NO children either, although he has forged deep friendships with some of his former students, including the tattoo artist Regino Gonzales (who gave him a bird on the right side of his neck) and the painter and former comic-book illustrator James Jean (who endowed a scholarship at S.V.A. in Woodruff’s name). Other Woodruffians have become graphic novelists (Farel Dalyrmple, Dash Shaw), children’s book authors (Steve Savage, Raina Telgemeier) and fine artists (Anthony Iacono, Mu Pan). Some of his protégés came with bouquets to his recent opening; the illustrator Yuko Shimizu, who now teaches at S.V.A. herself, brought her own class. To Shimizu, Woodruff has never been so calm. His retirement, she says, recalls yaku-otoshi, the Japanese term for when someone cuts one problem out of their life and the rest fall away. “You let everything loose and all of a sudden everything comes to you,” she explains. “That’s exactly what I feel is happening to him.”

With retirement came freedom, the very thing Woodruff was searching for when he started his teaching career. “It gave me a financial safety net, so I could make my own peculiar works without having the terrors of the art marketplace in my head,” he says. At the same time, Woodruff wanted his students to understand the realities of that marketplace. S.V.A. has no tenured professors and prides itself on hiring only working artists. Woodruff, who didn’t come from privilege, sees himself as a craftsman and intellect in a field overrun with lofty academics and snake oil salesmen. He wanted his students to learn the hustle that it takes to be an artist — to give them the kind of education he didn’t get. At Cooper Union in the 1970s, he sat through a drawing class taught by Hans Haacke, the conceptual artist who is best known for building an airtight plexiglass cube. “I think he took on the class as a bit of a lark,” says Woodruff, who honed his craft early on by drawing storyboards for the avant-garde theater director Robert Wilson and illustrating magazines and book covers.

By 2000, the year Woodruff was promoted to chair of his two departments, S.V.A.’s cartooning program offered courses in three tracks: penciling, inking and lettering. Woodruff hired the pioneering cartoonists Gary Panter and Keith Mayerson. He brought in figurative painters to teach basics while diversifying the curriculum, even adding a tattoo design course, the nation’s first of its kind. Enrollment grew, the illustration department more than doubled, and in 2020 its students won four of the top five awards doled out by the prestigious Society of Illustrators.

Through it all, Woodruff continued to teach. Some alumni call his practice of requiring drawing students to spend an entire semester erasing and correcting a single sketch “torture therapy,” but the entirety of one of Woodruff’s five-star reviews on the website RateMyProfessor.com reads, “He sees through you.” The painter Trey Abdella summarizes Woodruff’s style as “not buckling.” He says, “Tom was just like, ‘But why? What is the reason you’re doing this? Think about that.’” In response, Woodruff says, “It’s a deeply spiritual thing, teaching somebody to draw.”

And yet, he was never so focused on technique that he forgot the big picture: to teach people, too, how to live as artists. The painter TM Davy, who co-taught with Woodruff after graduating from S.V.A. and now leads his own classes there, noticed how Woodruff would do that by telling stories from his own life — like the time he dressed so wildly that Bill Cunningham photographed him at three different parties in one night, or how he learned to tattoo when it was still illegal in New York and ended up befriending Ed Hardy, with whom he then trekked to a remote Hawaiian island to visit the last leper colony, where he stood trembling atop the mass graves. “He would tell these stories to convey that life is a devastating but awesome adventure,” says Davy. “To teach people that freedom is possible. Not that it’s easy or that it’s available to everyone, but that there is work in art that can open that gate a little bit further.”

Since stepping down this past fall, Woodruff has found even more of that freedom: He sleeps in, makes art all day, and when he and his husband have finished dinner, they watch old movies together. He is making paintings for another show next spring at Vito Schnabel Gallery and is preparing for the release this fall of his graphic novel with the publisher Fantagraphics. There is now only one void. “Teaching drawing is the one thing that I kind of miss,” he says. In fact, during a visit to his gallery in April, he can’t resist giving an impromptu lesson in front of “Nest” (2022), a nine-foot painting of mottled dinosaur eggs. He looks past the foregrounded eggs to demonstrate how he’d reworked the landscape to achieve the effect of a receding desert. The things people don’t notice, he says, are what artists tend to spend the most time on. Examining the details in the distance, he says, “The space that’s in between here is what’s really hard.”