The Professor hears on the radio that a female pilot making a long trip is supposed to pass over the island. Luckily, the Skipper once turned a radio into a transmitter. Unluckily, he can't remember how unless he's asleep.
This episode includes examples of the following tropes:
- Agony of the Feet: The Skipper narrowly avoids stepping on the fire during one sleepwalking excursion. Gilligan, however, does step in it and suffers a very painful burn to the foot.
- Cassandra Truth: Gilligan tells the Skipper about his sleepwalking, but the older sailor doesn't believe him. Until the next morning, he insists that Gilligan was sleepwalking instead.
- Face Palm: When Gilligan chimes in and wakes up the Skipper again just as Ginger has almost sung him to sleep, the Professor covers his face with one hand.
- Fly Crazy: At the end, Gilligan, who's trying to swat a bug, hits the Skipper in the head.
- Counting Sheep: When Gilligan offers him a cup of warm coconut milk, the Skipper says he's already had too many glasses and never wants to see another, or a lamb chop, for that matter. Gilligan is confused, and the Skipper explains that he's counted a huge number of sheep while trying to fall asleep.
- Hand Gagging: When Gilligan gets a hotfoot from stepping in the fire, the Professor covers his mouth to prevent his noises of pain from awakening the Skipper before he shows them what they want to know.
- Hypocritical Humor: Gilligan goes to Mr. Howell to get some tranquilizers for the Skipper, without explaining why he wants them. As he walks away, Mr. Howell (who has a small box full of medicines) comments mockingly on the tendency for the younger generation to have medicines for anything and everything.
- Literary Allusion Title: The title adapts a line from Hamlet.
- Mistaken for Junkie: A variant; the Skipper keels over after downing two tranquilizers with already over-tranquilized mango juice. Seeing him flat on the ground, Mr. Howell thinks he's drunk on cocktails.
- Past Experience Nightmare: The Skipper suffers a nightmare about his past in the navy. He first turns a pretend radio into a transmitter using a screwdriver and wire cutters (actually Gilligan's fingers) while under enemy fire. Then he yells about a diver-bomber attack and sleepwalks back to the hut.
- Percussive Maintenance: After the initial attempt to turn the radio into a transmitter apparently fails, Gilligan manages to fix it by thumping the radio with one hand. Unfortunately, when he demonstrates to the Skipper a moment later, he knocks all the radio parts out of the back.
- Sleepwalking: The Skipper, suffering a nightmare about Guadalcanal, gets up from his hammock, walks out of the hut, fixes a pretend radio in his sleep, and then walks back without waking up.
- Slipping a Mickey: When the Skipper is too wound up to get to sleep, Gilligan borrows some tranquilizers from Mr. Howell to put in his mango juice. Unfortunately, the girls and the Professor also add some and then the Skipper, seeing the tranquilizers, uses the juice to take a couple. He's too tranquilized even to remain upright.
- Warm Milk Helps You Sleep: The Castaways substitute warm coconut milk.
- Yank the Dog's Chain: After a whole episode of trying to get the Skipper to sleep-fix the radio, a combination of his work and Gilligan's Percussive Maintenance succeeds in getting through to the pilot...only for Gilligan's demonstration of how he did it to knock out the radio's inner parts, just as she flies over.
