Among Robert Moses's unsuccessful development projects was an elevated expressway across Midtown Manhattan, with commercial development below the road and high-rises above it. One proposed route had the expressway passing right through the Empire State Building. I don't know how seriously this was considered - it's one thing to put up a building around a road and quite another to retrofit an existing building to put a road through it.

https://en.wikipedia.org/wiki/Mid-Manhattan_Expressway