The year is 1642, and the Stooges are garbage scow sailors stranded on Dead Man's Island. At first, the governor (Vernon Dent) finds it hard to believe that the trio are actually sailors due to their modern uniforms, but changes his mind once Curly starts flirting ("Hiya, babe!") with his fiancée, Rita (Christine McIntyre). The governor throws the Stooges in jail, and sentences them to death via burning at the stake.
Lucky for the Stooges, Rita has no interest in marrying the ruthless colonial governor and helps the boys escape by exposing some hidden tools. She then directs them to drill their way specifically through the west wall in order to escape safely. Unfortunately, the Stooges argue incessantly, choose the wrong wall, and land right right back in their cell.
Rita quickly suggests the boys disguise themselves as "wayfarers from a strange land" bringing priceless gifts. Curly is the great, nearsighted Maharaja of Canarsie who has domains on the isles of Coney and Long. Moe is the Gin of Rummy, and Larry is an accomplice. Moe and Curly exchange in conversations consisting of doublespeak and gibberish and offer the governor a raspberry lollipop, which he mistakes as a ruby as large as a turkey's egg. Moe dubs it the "Ruby de Lollipopskia." Next is a fountain pen that the governor mistakes as a tusk from a black walrus. The governor is delighted with these gifts, and requests that the Maharaja bring him some fair damsels. Honoring his request, the Stooges escape quickly, not wasting a moment. However, the governor's secretary (Dorothy DeHaven) reveals the Stooges' true identities, and the governor is livid. Once he learns they are headed to the cutthroat pirate Black Louie's, however, he enlists the scoundrel's help to kill the escaped sailor Stooges.
The Stooges meet Black Louie (Robert Kellard) at a sa;loon, and engage in a game of target practice. They enlist a reluctant Larry as the live target, and begin the knife-throwing. In the interim, Rita quietly makes her presence known to the boys, and alerts them of the governor's plan. They realize they must flee, but Curly's awkward knife throwing (thanks to his glasses containing lenses as thick as soda bottles) puts Black Louie on the defense. The fight breaks out in the saloon, with the Stooges winning out. Moe proclaims himself "Emperor Moe" of Deadman's Island-until a knockout hammer on a pinball machine bonks him into the "Maharaja Routine"-and the Stoogers and Rita escape.
- Moe Howard as Moe
- Larry Fine as Larry
- Curly Howard as Curly
- Christine McIntyre as Rita Yolanda
- Vernon Dent as Governor
- Robert Kellard as Black Louie
- Three Little Pirates was filmed after 42-year-old Curly Howard had suffered a series of minor strokes. As a result of his illness, Curly's performances had been marred by slurred speech and slower timing. Much of the action in previous films (Three Loan Wolves, G.I. Wanna Home) had been shifted away from the ailing Stooge and placed in the hands of co-stars Moe Howard and Larry Fine.
- However, Curly was on his game during the filming of Three Little Pirates. Though still not 100% himself, the comedian performed the memorable "Maharaja" routine with Moe almost flawlessly. He continued to display his formidable gift for physical comedy; for example, in one shot, he briefly assumes a reclining position while seated on a chair. Director Edward Bernds recalled the progression of Curly's decline through each film in the order they were made (vs. released):“ I guess I should be thankful that Curly was in one of his 'up' periods, because it was strange the way he went up and down. He was down for A Bird in the Head and The Three Troubledoers, he was up for Micro-Phonies, way down for Monkey Businessmen. In Three Little Pirates, he was terrific. It was the last flash of the old Curly.
- It has been said that the Stooge releases of 1946 were the worst batch since they joined Columbia Pictures. Much of this can be attributed to Curly's languid performances. In retrospect, Three Little Pirates turned out to be the only real standout of the year.