For decades he was a successful stage actor, first in England and then in the United States. But it was as an actor in Hollywood that he is best remembered. John Houston cast him as Kasper Gutman, known as "the fat man" in the film The Maltese Falcon. Along with his cohort in crime, Joel Cairo (played by Peter Lorre), the pair sought an elusive jewel encrusted statue worth a fortune. Their search pitted them against Sam Spade, played by Humphrey Bogart. The movie was a critical and financial success, and it established Greenstreet as a character actor who would go on to play the villain in nearly two dozen films. His weight (nearly 300 pounds) and his piercing hawk-like eyes, gave him an ominous presence, and his stage acting experience allowed him to deliver lines that became classic quotes among fans of film noir.
After his film debut he went on to star in numerous films recognized as classics today, including Casablanca, Passage to Marseille, The Mask of Dimitrios, and The Verdict. In all he made 24 films in a Hollywood career that lasted only eight years. Yet his impact has been remarkable. He was the perfect villain, a man who spoke politely and with a rich vocabulary, and yet could be ruthless. He was often paired with Peter Lorre, with whom he made nine films. Greenstreet even helped inspire the alien villain in Star Wars. When receiving instructions from George Lucas on how to create Jabba the Hut, the designer thought of Sidney Greenstreet. It was a comparison Greenstreet would have appreciated.
"Talking’s something you can’t do judiciously unless you keep in practice, and I’ll tell you right out that I’m a man who likes talking to a man that likes to talk."
- Kasper Gutman, The Maltese Falcon