Goodbye Old Paint

Goodbye Old Paint is the 34th episode of the first season. It first aired May 22, 1965.

Synopsis
After fishing in the Lagoon, Gilligan heads back to the hut area and passes a strange painting he's never seen before. As everyone is checking it out and commenting on it, the owner of the painting, Alexandri Gregor Dubov, emerges from the jungle complaining that it's upside-down. The Howells recognize Dubov, explaining to Gilligan that he left civilization years before, after having his talent and accomplishments recognized. Loud, obnoxious and demanding, Dubov orders them off the Island, but after realizing the Castaways are stranded with him, he begins taking advantage of their food, provisions and hospitality, even taking over the Boy's Hut, kicking the Skipper out of it. Mary Ann soon discovers that Dubov has a transmitter and can call a boat as soon as he wants. Mr. Howell concocts a plan to have Dubov paint a portrait of Ginger that they will all rave over and get Dubov's ego prompted enough to want to return to civilization. Ginger goes through a lot of grief over the painting which is so incredibly surreal with distorted geometric shapes that is not really a portrait, but the plan works up until Gilligan blabs out loud the stunt to get Dubov to take them all off the island. Dubov is upset and marches off into the jungle as Mr. Howell and the others get upset. Gilligan soon apologizes to him after Mr. Howell has cooled off, later confessing that he flunked out of art in the third grade. That's when Mr. Howell gets another idea to pose Gilligan as a rival genius painter and return to civilization to have the critics decide who is the better painter between them. Gilligan gets the Skipper to pose for him and creates a painting that is but a few brush-strokes on a canvas. Everyone raves over it, and Mr. Howell convinces Dubov that his paintings are now worthless. With everyone praising and showering Gilligan with praise, Dubov goes to the skinny first mate for art lessons in return for the transmitter. Unfortunately, as the Professor analyzes it, everyone realizes that it's rusted and corroded from all its years on the island. Howell starts crying that they're still stranded, but the Skipper puts Gilligan's new talent to work by having him paint sealant on the hut.

Message

 * "Art, like beauty, is in the eye of the beholder."

Highlights

 * Mr. Howell giving Gilligan his teddy bear to sleep with
 * Ginger getting angry about Dubov's painting
 * Gilligan attempting to paint a picture of Skipper
 * Gilligan reading Dubov's letter in Dubov's voice

Credits
Main Cast
 * Bob Denver as Gilligan
 * Alan Hale, Jr. as The Skipper
 * Jim Backus as Mr. Howell
 * Natalie Schafer as Mrs. Howell
 * Tina Louise as Ginger
 * Dawn Wells as Mary Ann
 * Russell Johnson as The Professor

Guest Cast
 * Harold J. Stone as Alexandri Gregor Dubov

Trivia

 * The name of the episode comes from "Goodbye Old Paint," a song by Western entertainer Tex Ritter.
 * When Gilligan and the Howells meet Dubov near the lagoon, mountains can be seen in the distance.
 * Chronologically, Dubov would have arrived on the island around 1953 about the time Jungle Boy might have arrived on the island as an infant. There is no known connection between them.
 * Considering Wrongway Feldman arrived on the island during the Late Twenties to Early Thirties, he might have been aware of Dubov and Jungle Boy on the island, but this is unconfirmed.
 * Dubov seems to be familiar with some of the film stars of the Silent Movie and early-Talkie era, particularly Mae Busch. It is possible he may have done an abstract portrait of her decades before landing on the island. This fact also fits with the theory he landed on the island in the Early Fifties.
 * Since Dubov floats away on a raft made from his paintings, it's unclear why the Castaways can't do the same thing.
 * When Gilligan and the Howells first meet Dubov at the lagoon, the artist complains that his artwork is displayed upside down; however, Dubov must have done that himself as nobody else has touched the work.
 * When Ginger poses for Dubov, for some unexplained reason she stands with her back to him.

Quotes
Mr. Howell - "It's ridiculous." Gilligan - "It's scary." Dubov - "Nincompoopers, it's upside down!"
 * Mrs. Howell - "There's no doubt that it's abstract."

Gilligan "It looks like a couple of hard-boiled eggs." Dubov - "Peasant! It is scrambled eggs."
 * Dubov - (about painting) "What is that called?"

Dubov "First thing, telling you to get off."
 * Mr. Howell - "What are you doing on this island?"

Dubov - "Don't have boat." Professor - "Then you can't get off." Dubov - "Can get off." Gilligan "How?" Dubov - "By boat." Gilligan - "You just said you didn't have a boat." Dubov - "Have transmitter. Call boat."
 * Gilligan - "We looked all over the island. We couldn't find a boat.'

Skipper "Give me one good reason." Gilligan "He's got a transmitter." Skipper "Well that's a good reason."
 * Professor "Skipper, we have got to be nice to him."

Gilligan - "I must be gorgeous."
 * Mr. Howell - "Yes, and the beauty of this plan is it's simplicity. Because the more simple a thing is, the more beautiful it is."

Gilligan - "Oh yeah, I can kind of see her lungs and appendix now."
 * Mr. Howell - "What he has painted here is, what we might say the inner woman."

Gilligan "What?" Mr. Howell - "Unencumbered. Don't you paint unencumbered?" Gilligan - "Sure, and I can draw radishes too."
 * Mr. Howell - "What he has is the ability to remain unencumbered.'

Gilligan - "You know what you look like?'
 * Skipper - "Well, you know what - what I feel like?'

Skipper - "Gilligan, if I lift up the other foot I'll fall on the ground." Gilligan - "Well, you never know, Skipper, Why don't you just try it. Just lift it up and give it a little..." Skipper "Gilligan, will you get behind that easel and paint!"
 * Gilligan - "Yeah. Now lift up the other foot."

Skipper - "See it? I posed for it." Dubov - "You pose for that picture?" Skipper - "Certainly. That was the real me. The man of the sea sailing into the wind, with my bare hands fighting the ocean." Dubov - "Dubov want to tell you something. I saw picture. You lost fight."
 * Dubov - "You saw painting of skinny kiddo?"

Gilligan - "It's easier than coming up on stuff by itself."
 * Skipper - "Gilligan, must you repeat everything I say?"