A versatile performer with 40 years' experience on the stage, had shunned Hollywood until John Huston offered him the role of Kasper Gutman, the loquacious, enigmatic villain of The Maltese Falcon (1941). Greenstreet was masterful in the part, delighting audiences, astounding critics, and securing an Oscar nomination. (He also helped promote the film with an unforgettable coming-attractions trailer, the success of which led to similar duties for many of his subsequent Warner Bros. films.) He was reunited with Falcon star Humphrey Bogart in several movies (including the classic Casablanca) but he seemed most at ease opposite wily, diminutive Peter Lorre. Vintage matte-finish 6.5 x 8.5 Lang portrait of Greenstreet as Henry the VIII, signed and inscribed “To Margaret, I expect fine things of you, Sydney Greenstreet, 1918.” In fine condition, with light silvering to the image edges. A rare and unusual image. PSA/DNA COA and R&R COA.