The Pirate was filmed in 1948, when Judy was 26.
Unfortunately, The Pirate marked the beginning of the end of Judy's career, as she was having issues with drugs and whatnot.
Because of this, she missed 99 out of 135 days of rehearsal! Gene Kelly, her co-star, pretended to be sick one of the weeks she was out, and both he and Vincente Minnelli (The Pirate's director as well as Judy's wife at the time) went out of their way to help her.
Despite this, The Pirate is said to be one of Judy's best films.
One of my favorite parts of this film is when Judy sings: "Mack the Black."