Why The Skipper Was The Hardest Role To Cast In Gilligan's Island

Walter White and Jesse Pinkman. Kirk and Spock. Joey and Chandler. Memorable TV pairings are a dime a dozen, but truly legendary combinations like these, in which the actors are operating at the peak of their powers and their shared chemistry is off the charts, are much harder to come by. One such couple (of the non-romantic variety) that has entered that hallowed pantheon is Gilligan and the Skipper from the classic 1960s sitcom "Gilligan's Island," where actors Bob Denver and Alan Hale Jr. became beloved stars playing two of the seven castaways who became stranded after a storm washed their characters up on an island during the fateful three-hour tour we hear about in the show's ear-wormy theme song.

Sherwood Schwartz, the show's creator and producer, knew how crucial it was to cast the right performers for these roles, and for him, the Skipper was actually the hardest part to cast on the entire series. In a retrospective interview with the Television Academy Foundation, Schwartz laid out his conundrum like this:

"I always knew that the most difficult person to cast would be the Skipper. I always knew that, and it proved to be the case. Because I wanted a big guy — a physically big guy — bellowing at Gilligan, who was going to be a smaller, thinner person. And you need a teddy bear. Not a bear. A teddy bear. So he has such warmth that you know that, no matter how much he yells at Gilligan, that he really likes him. Loves him. That's a hard thing to find."

Schwartz tested a ton of actors for the role by running them through the paces of performing what he calls "a particularly difficult two pages" where the Skipper was heavily lambasting Gilligan. "I knew if you could survive that scene, you were the right guy for 'Gilligan's Island,'" he said. But actually finding the right person for the role came right down to the wire, because everyone he tested "turned dark when they started to yell at Gilligan," and that simply wouldn't work for this character. Thankfully, a chance meeting at a restaurant turned everything around.

'There he is! That's the Skipper!'

Two weeks before filming began in Hawaii, Schwartz was in trouble because he hadn't cast the Skipper role yet. But while eating dinner with his wife one night in Los Angeles, he happened to spot Alan Hale Jr. across the room, and inspiration struck. "I thought, 'There he is! That's the Skipper!'" he said. When Schwartz called Hale's agent the following morning requesting a screen test between Hale and Bob Denver so the brass at CBS could approve the casting, the agent informed him that Hale had taken an early morning flight to Utah to shoot a Western. Due to the nature of his contract on that film, the actor had to shoot six-day weeks — meaning the only time he could potentially get back to L.A. to shoot the screen test would be on a Sunday. The way he told it, Schwartz convinced the powers that be to open the facilities on a weekend so they could film the test, and CBS finally approved with only days to spare before production began.

Thinking about the dynamics between characters in this show, Schwartz was absolutely right to put so much pressure on himself to find the right person to play the Skipper. (Gilligan's full name may have been a subject of controversy, but the Skipper's full name was Jonas Grumby.) The relationship between Gilligan and the Skipper is by far the most important one of the entire series, and while it's fun to see different combinations of characters highlighted throughout the show's run, those characters feel more like supporting players in this zany story. The show truly lives and dies on the chemistry between the men in red and blue.

If writer Charlie Kaufman had gotten his way and made a "Gilligan's Island" reboot in which the castaways engaged in cannibalism, I wonder if the Skipper's mostly good-natured pummeling of Gilligan would have taken a much darker turn.