I had the frustrating experience of trying to install matplotlib on a fresh/clean installation of Windows 10 the other day, for hours on end the import matplotlib failed with ImportError: DLL load failed.

It turned out to be kiwisolver, which was missing Microsoft Visual C++ Redistributable 2015/2017.

In _check_versions() in lib/matplotlib/__init__.py could catch the exception and show a hint like: You likely miss Microsoft Visual C++ Redistributable 2015/2017.