(Photo: Courtesy of Christie's Images Ltd 2007)

5. Paul Outerbridge
Self Portrait, circa 1927. Vintage gelatin-silver print; probably unique.

Estimate: $40,000 to $60,000. Outerbridge was the Cindy Sherman of his day, dressing himself up for mock-comic, disturbing self-portraits. He was also an early adopter of color photography as well as an innovator of erotica.

Market details: Although Outerbridge made another photograph from the same sitting, this print is thought by Christie’s to be unique, making it especially desirable.

Prospects: A solitary print by an acknowledged master of the medium (if not exactly a household name) makes this the perfect buy for true collectors. It takes only two of them to bid up an excellent price.