The Rise and Fall of the Bob Ross NFT King
How one artist rode the NFT wave to fame — and then crashed with it.

(Chris Cuffaro)
The most ridiculous and remarkable year of Jay Weinberg’s life is captured in a single photo. It’s November 2021, and he’s standing in the middle of Times Square in a pose of solemn triumph, brandishing a raised paintbrush in his right hand while wearing a curly wig and an all-denim outfit — an homage to his personal hero, the eccentric painter Bob Ross. You’d be excused for assuming that Weinberg was just another costumed New Yorker looking for quick bucks from tourists. But this was no joke — at least it wasn’t meant to be.
Weinberg, a northwestern Indiana artist, was visiting New York City as crypto royalty to be. That year, he was nominated for the “best traditional artist turned NFT artist” award at NFT.NYC, an annual conference dubbed the “Super Bowl of NFTs.” The costume was both a tribute to Ross and promotion for Weinberg’s ambitious NFT project, in which he turned various portraits of the soft-spoken host of the 1980s PBS show The Joy of Painting into a set of NFTs called “Happy Little Hairdos.”
Remember NFTs? It might feel like a hallucination now, but in the pandemic-stricken years of 2020 and 2021, a restless and screen-bound public was seized by a new kind of digital gold rush: non-fungible tokens. The pitch was simple: most digital currencies like Bitcoin and Dogecoin were ethereal, a string of digits on a crypto app. NFTs offered a way to marry visual art to blockchain technology, making them individually ownable, tradable, and — most important — easily sellable. For a brief moment, they promised a cultural revolution in which artists would bypass galleries and gatekeepers to sell art directly to their audiences.