I thought it was a gag the first time I stumbled upon it. But there it was: Van Winkle Special Reserve 12 Year Lot “B” with the visage of septuagenarian rock god Mick Jagger hand-painted onto the bottle. Offered on Charitybuzz, an online auction site that has long featured “extraordinary experiences” to raise money for worthy causes, this unique item sold for over $3,000.

I soon found myself down one of the strangest rabbit holes I’ve ever traveled in my career of studying the buying habits of American whiskey collectors.

You see, Jagger Van Winkle wasn’t the only example of this potable art form.

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Scouring the internet I found a Paul McCartney one, the cutest Beatle holding his bass just below the Van Winkle label. Here’s Tom Brady on a bottle, scanning the line of scrimmage before the snap. There’s also Tom Brady and Gronk, the dynamic duo painted onto a bottle of Old Rip Van Winkle 10 Year (or “10 Year Pappy,” according to the auction listing).

I’m used to whiskey dorks collecting questionably rare items: cartoonish sticker-clad bottles, Blanton’s with specific dump dates, anything Smoke Wagon. But this, I surely thought, was the apex of the modern whiskey collector’s demand for the obscure and limited.

I would eventually track down the genius behind these Pappy portraitures at his home/studio in the Nolita neighborhood of Manhattan.

Mick Jagger hand-painted onto a bottle of Pappy

Fine Art and Rare Bottles

With a master’s degree from Columbia University’s Teachers College, Mark Kannell had no plans to enter the art world. It simply didn’t seem like a feasible career to him. But before settling down as a full-time teacher, he decided to give it one last shot.

​​Starting in 2013, the New Jersey man began painting images of professional athletes like local heroes Derek Jeter and Eli Manning; he landed an agent and found a gallery, but his sales were few and far between. Then the pandemic rolled around and Kannell started showing off some of his more unusual pieces on TikTok. Last May, before I was even aware of Kannell, I recall a time-lapse video of him painting the iconic image of Michael Jordan’s NCAA championship-winning jumper onto his No. 23 North Carolina jersey randomly coming across my feed.

Because of TikToks like that, Kannell had gone viral and was getting hundreds of DMs and emails a day. One of those was from Ben Erwin and ​​Riley Voss at Charitybuzz who, like so many others, had been recently forced to change their business model.

“Our business is historically centered around intimate experiences with celebrities, athletes, musicians at large-scale events,” says Erwin, the company’s CEO. Since Charitybuzz was founded in 2005, they have raised $550 million for charitable causes. When the pandemic hit, countless charities were really hurting for money, and so Erwin and his team were looking to offer more collectibles, a market that had exploded during lockdown. “We were trying to figure out what we could do to meet the realities of this new world,” he says.

They had already seen a one-year 270 percent growth in the sales of high-end bourbon on the site, so they knew there was an eager market. It was approaching the holiday season of 2020 and Charitybuzz made an unusual request: If they sent Kannell rare bottles of Van Winkle, could he paint an image of Julian “Pappy” Van Winkle Sr.’s iconic side-profile, topped with a Santa hat, onto the bottle’s shoulder? He was up to the task.

“I knew a little about the Pappy market,” says Kannell, who is an avid whiskey drinker but not a high-level collector or connoisseur. “So I figured it would sell just based on it being a Pappy bottle — and this made it unique, one-of-a-kind.”

It would just need a buyer.

“This Is So Cool”

Brady Pedler is a wealth manager in the Tampa, Fla., area. In his 8,000-square-foot home, Pedler has one of the most impressive personal whiskey collections I’ve ever seen, with over 2,000 bottles featuring such unicorns of unicorns like the 19 Year Old Corti Brothers, 18 Year Old Blue Smoke, and Red Hook Rye. Last year alone, Pedler claims he spent $400,000 on rare whiskey.

“I’ve been blessed. I grew up with nothing. I’m self-made, not some big swinging dick, but I spend money on what I enjoy,” says Pedler. “When I first came across [Kannell’s] bottles, I thought, ‘This is so cool.’”

His first acquisition was literally Kannell’s first piece of Pappy art; Pedler spent $5,000 on it. (Though a standard 10 Year bottle retails for $80, its actual market value is closer to $500.)

The funniest thing is, Pedler doesn’t even drink.

But he does collect and he instantly wanted more of Kannell’s work. He would quickly become the Charles Saatchi to Kannell’s Damien Hirst.

“His art is unbelievable,” says Pedler. “Anyone who sees it does not even believe it’s real.”

Luckily, Charitybuzz was likewise so pleased with Kannell’s first work that it began commissioning more.

“We expanded to commemorate moments in time,” says Voss, Charitybuzz’s VP of business development.

Next up and on the heels of Tampa Bay versus Kansas City in Super Bowl LV: starting quarterbacks Tom Brady and Patrick Mahomes. Pedler bought both of those as well and was even able to get the former signed by Brady at a charity event (“What is that?!” the stunned player asked him). Peddler would eventually buy a Clint Eastwood and the Jagger one, too.

Today on his top shelf sits seven sealed Van Winkle bottles with Kannell’s paintings on them. A generous collector who loves sharing with his friends that do drink, they’re some of the only bottles in his collection he never plans to open.

“I don’t know how you put a value on them,” says Pedler. “Maybe people would appreciate [Kannell’s art] just as much on a bottle of Jack Daniel’s, but if you’re interested in Pappy and interested in the artwork, it’s a total unicorn.”

Tom Brady hand-painted onto a bottle of Pappy

Like Doing Heart Surgery

By now Kannell estimates he has done 50 or 60 bottles and the requests keep coming in. From Charitybuzz, which  simply can’t list enough of his bottles, from average Joes who find him on TikTok and Instagram and instantly want to commission their own (Can you do a Josh Allen? Can you do a Luka?); I’m even aware of an NFL Hall of Famer who will soon have a bottle with his own image on it from his playing days.

It’s not strictly the 10 Year and 12 Year bottles being used as canvases, either. Recently, Kannell was sent two Pappy Van Winkle 23 Year Olds.

“I was really nervous to paint on those,” he admits. They hold around a $3,000 secondary market value and have a much smaller glass space to even paint on due to the additional age statement ring around the neck. “When you’re painting on one of those, you can’t mess up. I have towels underneath, and I treat it like I’m doing heart surgery,” he says.

It’s no longer just rock and jocks, either. One of Kannell’s weirder commissions was Elon Musk on a bottle of his Tesla Tequila. He’s likewise done Dave Portnoy, Barstool Sports’ controversial founder.

“The zeitgeist or media cycle will increase the perceived value of a certain opportunity,” says Erwin. “How do you marry those together [with a bottle of Van Winkle]? That’s essentially the genesis of the idea.”

More unbelievable than those, perhaps, is Kannell’s bottle art of Donald Trump, the former guy portrayed slim and buff, topless in American flag boxing trunks and a satin robe. Though Kannell claims he is apolitical and it was just a job, Trump even signed the bottle, his inscription reading “Trump: 2 Impeachment: 0.” Kannell eventually ran into the ex-president at an event in Naples, Fla., and introduced himself.

“I’m the Pappy artist,” he told the famed teetotaler upon introduction.

“I’m taking one of those home with me,” Trump responded concerning the bottles.

Donald Trump hand-painted onto a bottle of Pappy

One Expensive Canvas

Of course, the whiskey collecting world is full of as many haters as taters and, no surprise, a lot of people get really angry that Kannell is not only “defacing” pricey bottles, but, in many cases, rendering them something that will never be opened nor tasted. (For what it’s worth, Kannell has only tasted one single, tiny sample of Van Winkle in his entire life, at a liquor store that was holding a lottery for it.)

“I can’t even find Pappy and this guy is turning it into a work of art!” yelled a guy on TikTok recently.

“That’s one expensive canvas,” wrote another man.

“[Is it] worth less or more now?” wondered another.

That seems to be the prevailing question for the kinds of people who actually care about this stuff. Pedler believes these bottles will “hold their value,” but really something is only as valuable as any other person is willing to pay for it. And, over a year after he started, people are still willing to pay a lot for Kannell’s “Pappy art.”

“It gives them an additional level of exclusivity that has always been important in driving sales,” says Voss.

In the weeks leading up to this year’s Super Bowl, Kannell was cranking out players from each team. Bengals quarterback Joe Burrow. Rams signal caller Matt Stafford. This timelapse of Kannell making a Cooper Kupp bottle is particularly impressive.

“It’s unbelievable I can wake up and just paint as a full-time job now,” Kannell says. “I didn’t know there was such a demand out there and now I can barely keep up with it.”