Real pirates tended to have very short careers. Edward Teach, better known as Blackbeard, was pretty typical, being active for only about two years from 1716 to 1718, before losing his head. Cartoon pirates, however, do generally much better. Captain Pugwash, a British cartoon pirate created by John Ryan, originated as a cartoon in newspapers and books in the 1950s, and later in various TV series through the 90s.
In the books and TV series, Captain Horatio Pugwash is a somewhat bombastic yet simple-minded captain who sails the high seas in his ship called the Black Pig, assisted by cabin boy Tom, pirates Willy and Barnabas, and Master Mate. His mortal enemy is Cut-Throat Jake, captain of the Flying Dustman. Oddly, while a pirate captain, Pugwash never seems to engage in much piracy and is often saved by Tom, the cabin boy, who is the smartest member of the crew. Here is Episode 1 from the 1974 series.