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We report the fabrication of thin films perforated by high aspect ratio helical or chevron pores by an extension of the glancing angle deposition (GLAD) technique. The perforated films were created by transferring the nanostructure of a GLAD template film into target materials such as polymers and spin-on-glasses and subsequently removing the template. The pore shapes are shown to be highly controllable and films designed to suit particular applications are discussed. By a double templating technique, we replicate the structure of the original film using alternate materials, which are typically less suited to the unmodified GLAD technique. Helical films of Cu and Ni were created by this method and the process should be transferable to additional electrodeposited materials. The optical rotatory power of perforated thin films formed on glass substrates was characterized and perforated films were shown to be effective in rotating the polarization plane of linearly polarized incident light by as much as 1.4°/μm.