Computer Generated Holograms (CGHs) are used for wavefront shaping and complex optics testing. Present technology allows for recording binary CGHs. We propose a Digital Micro-mirror Device (DMD) as a reconfigurable mask, to record rewritable binary and grayscale CGHs on a photochromic plate. Opaque at rest, this plate becomes transparent when it is illuminated with visible light of suitable wavelength. We have successfully recorded the very first amplitude grayscale CGH, with a contrast greater than 50, which was reconstructed with a high fidelity in shape, intensity, size and location. These results reveal the high potential of this method for generating programmable/rewritable grayscale CGHs, which combine DMDs and photochromic substrates.