Played by Alan Hale Jr., the Skipper (the character's actual name was rarely mentioned after the show's pilot episode) was the owner and captain of the S. S. Minnow on its "three-hour tour" from Hawaii when he, first mate Gilligan (portrayed by Bob Denver), and their tourist passengers were caught in a violent storm and stranded on a deserted island.

He acts often in his legal role as the group's leader, albeit with a decidedly collegial and democratic bent; the only individual whom he routinely orders about is Gilligan.

In times of crisis, the Skipper tends to defer to the more level-headed and educated passenger, Professor Roy Hinkley (portrayed by Russell Johnson).

Little was ever learned about his past, but in several episodes he mentions variously having several ships blown out from under him, and his veteran's status, implying that he had served in World War II.

In one episode he gets amnesia, and thinks he is on a covert mission behind enemy lines, mistaking the others for Japanese soldiers, including Ginger, whom he mistakenly believes to be a ventriloquist.