It's a good question whether Banksy really is a crossover, or only a crossover in market terms. I would definitely call him a high master of stencil technique though, some of that stuff is pretty hard to pull off.

As clever as his art is, I think he's still very much an outsider in the capital-W Art World, which for his part he's often trying to prank. (Which they richly deserve, see Exit Through the Gift Shop.)

Things like the self-destroying painting were high-concept but also completely staged. For another artist getting rich off his contempt for the Art Market, but solidly on the Art World side of the fence, see Maurizio Cattelan.

One person with a foot in both worlds is Alex Face but he's mostly known in South-East Asia. I have a feeling it'd be easier to find examples in Asia than in the West.

https://www.artsy.net/artist/alex-face