Choosing headshots taken either on film or digitally, does not have to be a hard decision.  Aside from cost, the differences between the two are not paramount.  As a photographer, I was trained to expose and process film as well as expose and process the final prints.  The darkroom is my home for most of this process, which incidentally has a large overhead due to supplies, time and upkeep.  With digital photographs and headshots, the darkroom is now the computer - and the time and upkeep is enormously cut down.  Although the hardware itself can have more startup costs, in the long run, digital photography is more cost-effective and time efficient.

To the untrained eye, there can appear to be no difference at all between film and high-end digital prints.  35 mm prints that have been digitized from film negatives or prints possess a heightened degree of color saturation and detail.  However, looking at a digital image that has been properly metered and exposed to the necessary digital filters will show extreme likeness to digitized film. The largest factor in achieving this likeness is in the quality of the equipment used.  First of all, you must understand that not just any $500 point-and-shoot digital camera is going to come through in creating film-like headshots.  Just as a standard video camera is not going to come close to the look a moving picture film camera can create, professional, digital images need to be captured with a professional camera.  In motion pictures, this would be par to using High Definition and 24p digital video cameras. 

I personally use the Nikon D70, which has over 6 million effective pixels, and shoots an image size up to 3008 x 2000 pixels, and which like Single Lens Reflex (SLR) cameras, lets the photographer make vital adjustments that standard digital cameras cannot afford.  Having full manual functionality in a camera, including aperture size and shutter speed controls, exposure modes, bracketing capabilities, depth of field preview, as well as compatibility with variable focal-length lenses is essential to creating professional quality digital headshots.

As a photographer, I personally have no qualms if you prefer to have your headshots taken on film.  I personally appreciate some of the finer aspects that film has over digital. I also work with a professional film SLR, and will shoot the same headshot packages (see Headshot Packages).  Just keep in mind that it will cost more.