We have investigated the structure, defects and plasticity of thermally evaporated thin films of the organic molecular semiconductor pentacene using X-ray Diffraction (XRD), Optical microscopy (OM), Transmission Electron Microscopy (TEM), Electron Diffraction (ED), and High Resolution Electron Microscopy (HREM). Using XRD the degree of (001) texturing present in the as-grown films was characterized. The nature of pentacene plasticity and deformation-induced molecular alignment was investigated using rubbing and scratching techniques, as well as nanoindentation. Rubbing of the bulk powder produced thin oriented films, and a deformation length scale dependence was seen. Under stress pentacene crystals initially fail by cracking, until they reach a critical size of about one micron, when they tend to plastically deform into thin sheets. Alignment of thermally evaporated films was achieved under a controlled load scratch, and the degree of molecular orientation inside the scratched region was directly imaged using HREM. Finally, using nanoindentation we measured pentacene's plastic hardness to be 0.25 GPa at a loading rate 0.05 mN/s. A loading rate dependence of the hardness and stiffness was measured, with thin films behaving harder and stiffer at faster indentation rates.