In 1983, Woody Jackson got a call from a Vermont entrepreneur named Ben Cohen. Jackson, newly graduated from Yale with an MFA in painting, was in the habit of painting cows and Cohen, along with his business partner, Jerry Greenfield, were looking for a logo for their growing ice-cream business. Forty years later, the cows Jackson painted for Ben & Jerry’s still adorn the company’s pints and Jackson is still painting holsteins.
When I was a kid, Ben & Jerry’s tees with Jackson’s cow were standard-issue summer-camp gear. Most of the shirts are straight-ahead shots of the longstanding cow mascot, painted by Jackson, but a few are more involved, all-over-print tie-dye shirts in pastoral colors that the cooler kids wore. As an adult, I wanted one for myself and, searching eBay, discovered a whole world of Woody Jackson tees, and then a universe of paintings, books, and more. Ben & Jerry’s shirts were just an entrée into Jackson’s enormous catalogue of cow art and merch.
Across decades, he’s found new ways for cows to graze and lounge. They come in packs, stand alone. There are calves, heifers, barns, rivers. In his paintings, mostly verdant landscapes, the sky is an infinite amount of colors, as if the aurora borealis were visible from New England every day and night. The cows, however, are always black-and-white.
Beginning in the ’80s Jackson’s cows were a lucrative business, and at one point he employed 25 people. He’s a solo operation now, but even at 75 he’s still pumping out cow books, pillows, mugs, notepads, water bottles, and more. Some of his products are straightforward reproductions of his paintings, but in the ’80s and ’90s, Jackson, an avowed lover of puns, churned out cow-parody shirts that now pop up regularly on eBay. For some time now, I’ve been buying them, along with any other Jackson offering I can get my hooves on.
Jackson sells an annual “cowlendar.” Each month is a cow painting corresponding to the weather. I prefer the winter months, when the landscape is dotted with snow. Jackson also notes each date there is a “full moo.” Many people tell me they use a shared Google Cal with their family, but my wife and I just hang one of these in the kitchen. The 2025 edition is already on sale.
Though Ben & Jerry’s has been around for 45 years, the company hasn’t been independent since 2000, when they were purchased by Unilever. Unilever recently implemented serious layoffs to the ice cream brand. Another dumb move is the lack of Woody Jackson logo merch available. You can buy a ton of B&J’s stuff (need a camo hat with a headlamp?) but nothing with the cow. For that, you’ll have to hit eBay, Etsy, Depop, Mercari, or another resale site. But the company sold a lot of the shirts pre-Unilever, and the cow shirts come up very regularly in a rainbow collection of colors. I have one in this deep green. A subtle nod to grazing.
In the ’80s and ’90s, T-shirts were where Jackson really went nuts with the puns. A spotted convertible? A “cowdillac.” A cow dressed up in western garb? A “cowpoke.” There are “kangamoos” and an anthropomorphized cow version of Uncle Sam saying he wants “moo.” The most over-the-top shirt is the now deeply dated drawing of a cow in military garb, labeled as Gulf War general Norman “Schwarzkow.” But I’m coveting a Simpsons parody T-shirt, “Bart Holstein.” The punchline here, an inverse of Bart’s signature “Don’t have a cow, man!” is “Don’t have a cartoon, man!” Not the most smooth rejoinder and all the more perfect for it.
My toddler daughter has had one of these for every stage of her life. Every time she outgrows it, we get a bigger one in a new color. Yellow, so far, is her favorite. When she wears it, she loves to look down at her stomach. Perhaps Woody can print some with the cows upside down.
In his children’s book, Counting Cows, which I often read to my daughter, he counts down the number of cows in a painting from ten to zero. “Four cautious cows” waiting in front of a barn, “Three hungry holsteins” grazing, etc. You expect that when you get to zero cows, that will be it. That page is a gorgeous shot of the forever rolling grass and the empty sky. A view untainted. But on the next page you can see the cows have snuck off from the field and headed to a party; they’re all dressed up to have a hoedown, with cowboy hats and neckerchiefs.
Jackson once did a host of merchandise, including posters and tote bags, for Middlebury College in Vermont (of which he is a graduate); they seem to have moved on to a more staid collection of wares. But the college still sells a collection of cow hats, including beanies. I prefer the trucker hats, better to let in the breeze.
The holstein holy grail is Woody original art. I’m lucky enough to own one wood piece — a cutout of a yellow painting my wife bought me as a gift in an auction. Jackson is incredibly prolific and has been painting for decades, so his original works are fairly widely available. He sells them himself on his website, or you can reach out to Edgewater Gallery, who represents him. They have a wider selection, including some work from the ’80s, like an artist proof for the piece Homestead, where the cows are more abstract, blobbier than in his current work.
Vermont shop Beau Ties carries a custom line of Jackson accessories. The cow-face mask is handy, and, if I had an occasion to wear a bowtie, I’m sure this would be the one. But the belt is a crucial utility piece. A little bit Dead Poets Society, a little bit 4-H club. Perhaps bovine prep will be a new trend.
In the center of Jackson’s watercolor Rolling Red Hills is a fiery burst of orange. It’s the first of the trees to change. In the foreground we see three cows. None of them are looking at the viewer; nor are they looking at the view. Both the trees and the lush indigo sky Jackson has brushed on above them are up to you to take in. “The cows have allowed me to bring them on the journey as I have learned to express myself with paint,” Jackson says in artist statement. In this painting, I don’t think it’s about the cows at all. They are bystanders to the action. For once, what he is painting is a world not only filled with cows, but briefly, blissfully empty of everything else.
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