The 6 Craziest NFTs in Art

November 17, 2021

Remember that time Grimes made $5.8 million on 10 pieces of digital art in 20 minutes? What if we said that’s nowhere near the craziest NFT art sale on record?

NFTs are one of the latest trends in the cryptocurrency sphere, and Grimes is not the only artist to cash in. In fact, NFTs are increasingly popular among digital artists as a way to make money on previously free art.

Here’s a look at some of the craziest sales of art NFTs on record and what they mean for future art investing.

Why Digital Artists Love NFTs

Unfortunately, digital art has long been undervalued as a form, largely because it’s widely available for free online. In other words, because there’s no scarcity, there’s no driving impulse to own the authentic original, which is a major factor in making an artwork valuable.

NFTs, or non-fungible tokens, are one-of-a-kind digital assets that can be bought and sold like any other asset. They’re recorded and verified on the blockchain network, making them impossible to counterfeit and crafting an easily traceable provenance. Most importantly, they add an element of scarcity previously unavailable to digital art, thus allowing digital artists to profit off their work by having an authenticated original work to sell.

The Craziest Art NFT Sales

The Internet is a wild place. Kind of like a rodeo, but with more cotton candy floss and disco balls and a bizarre sense of humor. That’s important to keep in mind when we talk about NFT art sales, which might be best understood as the culmination of modern internet culture.

Here’s a look at some of the biggest, craziest, and most unabashedly absurd art NFTs sold on the market.

The First 5000 Days

We couldn’t mention NFT sales without mentioning Beeple’s The First 5000 Days, if only because it remains a record-breaker. For Beeple, for Christie’s, and for NFTs. Up until this Christie’s auction, the auction house had never sold digital art before, and Beeple (a.k.a. Mike Winkelman) had never sold a print for more than $100.

That changed on March 11, 2021, when Beeple’s The First 5000 Days sold at auction for $69 million. Yes, a piece of digital art solely available as a JPEG sold for $69 million, and it positions Beeple among the top three most valuable living artists (just below David Hockney and Jeff Koons).

The work is a collage of 5,000 images that took 13 years to make. It started at a $100 opening bid, but then fevered competition between 350 bidders kicked in, helped along by Beeple’s popularity (2.5 million active followers across social channels) and Beeple’s reputation for being famously prolific.

Good Luck for Bad Luck Brian

Remember Bad Luck Brian, the meme that defined the year 2012? You know, that iconically awkward high school yearbook photo of a student in braces and an unmistakable red plaid sweater? Back in 2012, the photo was posted on Reddit, where users took to posting it with macro captions of impressively unfortunate events, the tamer of which include things like, “Buys a pet rock, it runs away,” and “Escapes from a burning building, gets hit by a fire truck.”

Thanks to NFTs, Kyle Craven (the pictured student) got the last laugh. On March 9, 2021, Craven auctioned the original yearbook photo as crypto art for 20 ethereum, or roughly $36,000.


You know a trend has taken off when even a toilet paper company gets in on it.

In March 2021, Charmin put five pieces of digital art up for bidding, titled NFTPs (as in, the world’s first Non-Fungible Toilet Paper) in the Twitter announcement. Bids ran the range from $500 to $2,100, with all but 0.01% donated to Direct Relief. The art includes decorated toilet paper rolls and various images of the brand’s mascots.

Sounds like a lot to spend on a toilet paper ad, but hey, it’s for charity.


We couldn’t talk about art NFTs without giving an honorable mention to Kevin McCoy’s Quantum, a.k.a. the first NFT ever minted.

Back on May 3, 2014, McCoy created Quantum as part of a presentation at Rhizome’s Seven on Seven Conference with collaborator Anil Dash. The pair were the first to conceive of putting digital art on blockchain.

What’s interesting about this piece of art is that it’s more than just gimmicky capitalization on Internet memes. Quantum is made entirely of code and the piece itself is generative, meaning it automatically permeates into new forms that are not predetermined at the outset or altered with any input from the owner.

The piece was the prizewinner of its Sotheby’s auction, raking in $1.47 million.

The Pixel and The Switch

Before there was Beeple, there was Pak, who began crafting NFTs anonymously in February 2020. Sotheby’s, eyeing the runaway success of Christie’s Beeple auction, turned to Pak to try to recreate a similarly profitable success.

Pak delivered with The Pixel and The Switch. It was part of Sotheby’s first-ever NFT art auction, which netted a total of $17 million. The Pixel sold for $1.36 million after a 90-minute war between 12 bidders. The kicker? The work is literally a single one-by-one gray pixel, the most basic unit of a digital image.

Pak’s most expensive work to date was sold at the very same Sotheby’s auction. That was The Switch, which sold for $1.4 million after fierce competition between 10 bidders. This one offers the owner a tantalizing choice: the owner has the option to trigger “the switch”, thus altering the work into a new, unknown image, but doing so is irreversible. Pak crafted it as a representation of how art is evolving in the digital realm.

Invest in Art to Invest in Your Future

Who knows if NFTs will be the future of the art world, but for now, they’re an exciting way for digital artists to make money.

Here at Masterworks, we believe art can do more than just inspire—it can help you build your financial future. That’s why we’re on a mission to democratize blue-chip art investing by allowing members to purchase shares in authenticated multi-million-dollar art with the highest potential risk-adjusted returns. We handle the research (with some help from Citi Bank and Bank of America) and you purchase your shares and collect dividends.

Masterworks is a fintech company democratizing the art market. Our investors are able to fractionally invest in $1mn+ works of art by some of the world's most famous and sought-after artists.