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In one of his productions of "Sherlock Holmes," he gave a young unknown actor the supporting role of Billy, the messenger boy. That actor was the later famous comedian Charles Chaplin.

Was the first actor to be universally acclaimed for portraying Sherlock Holmes, having staged the first authorized play in 1899.

As Holmes, he smoked a curved Meerschaum pipe, rather than the more accurate straight clay pipes that Holmes always smoked in the stories. Gillette did this because it was nearly impossible for him to do believable "business" with the clay pipes. Because of this, one of the stereotypical Holmes trademarks is a Meerschaum.

His home in East Haddam, CT, is known as Gillette Castle and is now a state park. The castle was built for him and contains many ingenious and unique items designed by him; for example, no two of the 47 interior doors are alike.

In 1882, Gillette married Helen Nichols of Detroit. She died in 1888 from peritonitis caused by a ruptured appendix. The couple had no children. He never remarried.