The Ten Best GILLIGAN’S ISLAND Episodes of Season One

Welcome to a new Sitcom Tuesday! Today we’re beginning our series on the best episodes from perhaps the most iconic show of the 1960s — Gilligan’s Island (1964-1967, CBS). All three seasons have been released on DVD and are available for free streaming to Amazon Prime members.


Just sit right back and you’ll hear a tale — a tale of a fateful trip that started from this tropic port aboard this tiny ship. The mate was a mighty sailin’ man; the skipper, brave and sure. Five passengers set sail that day for a three-hour tour. A three-hour tour. The weather started getting rough. The tiny ship was tossed. If not for the courage of the fearless crew, the Minnow would be lost. The Minnow would be lost. The ship set ground on the shore of this uncharted desert isle with Gilligan, the Skipper too, the Millionaire and his wife, the Movie Star, the Professor and Mary Ann. Here on Gilligan’s Isle!


Gilligan’s Island stars BOB DENVER as Gilligan, ALAN HALE, JR. as Skipper, JIM BACKUS as Thurston Howell III, NATALIE SCHAFER as Mrs. Howell, TINA LOUISE as Ginger Grant, RUSSELL JOHNSON as Professor, and DAWN WELLS as Mary Ann.


This series is probably the most memorable sitcom of the decade — renowned for its silliness, its fun, and its heart. Truthfully, the writing is never brilliant like Dick Van Dyke‘s but the show is consistently funny. In addition to a captivating premise, the series benefits from a truly amazing ensemble — both of characters and of actors. The seven castaways are superbly defined, almost by the first aired episode, and each performer is absolutely pitch perfect from the start. Season One is the only black-and-white season, and truthfully, it’s probably the weakest of the three. HOWEVER, Gilligan is one of those shows where almost every episode has something to offer. While the series doesn’t really kick into high gear until midway through the first season, the first half of the year is excellent in telling necessary stories and developing the characters. This was a tough list to make, and you’ll notice that I have many honorable mentions. But, I have picked ten episodes that I think exemplify the season’s strongest installments. For new fans, this list will give you a place to start. For seasoned fans, there might be a few surprises.


Here are my picks for the ten best episodes of Season One. (They are in AIRING ORDER.)


01) Episode 8: “Goodbye Island” (Aired: 11/21/64)

The castaways use tree sap to glue back together the battered Minnow.

Written by Albert E. Lewin & Burt Syler | Directed by John Rich

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This is one of only three episodes to feature scenes set on the beach upon which the castaways were initially shipwrecked. “Goodbye Island” is the first superb entry from the series, with a premise that unfolds organically and allows for several wonderful bits of physical comedy: the castaways trying to eat their pancakes, the Skipper and Gilligan getting glued to the boat, and the ship’s final loony destruction. The cast is great, the script is great; everything works.

02) Episode 14: “Water, Water Everywhere” (Aired: 01/02/65)

The castaways suffer a shortage of fresh water.

Written by Tom Waldman & Frank Waldman | Directed by Stanley Z. Cherry

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This episode made my list because of its solid premise that’s firmly rooted in reality. A shortage of clean water is a viable problem that shipwrecked castaways WOULD face, and the series enacts that with much humor. The sequence in which Gilligan must guard the fresh water is probably my favorite part of the installment, but many fans fondly remember Gilligan’s bit with the frog.

03) Episode 15: “So Sorry, My Island Now” (Aired: 01/09/65)

A WWII Japanese sailor lands on the island and captures the gang.

Written by David P. Harmon | Directed by Alan Crossland, Jr.

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This episode is a little bit politically incorrect today, but that doesn’t stop it from being hilarious. Vito Scotti is ridiculously amusing as the Japanese sailor, and the entire script is loaded with terrific one-liners and bits of comedy. My favorite moment is the interaction between the sailor and Mrs. Howell. Incidentally, this is one of those episodes that everyone seems to remember for its ridiculous premise (that was actually based on real life occurrences).

04) Episode 18: “‘X’ Marks The Spot” (Aired: 01/30/65)

The island is the target of a new Air Force missile, but does that mean rescue or destruction?

Written by Al Schwartz, Howard Merrill, & Howard Harris | Directed by Jack Arnold

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This episode marks the first time the series deals with stories involving space — a topic in which they’d revisit multiple times over the next two years. This episode isn’t one of the funniest installments, but it is one of the best written, with moments of earnest emotion from each castaway. Also, the idea that Gilligan is the only one that can diffuse the missile is perfectly Gilligan’s Island. So looney, so primed for failure, so enjoyable.

05) Episode 22: “Diamonds Are An Ape’s Best Friend” (Aired: 02/27/65)

A gorilla takes a liking to Mrs. Howell because of her perfume.

Written by Elroy Schwartz | Directed by Jack Arnold

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Any time an episode involves a primate (of any kind), you just know it’s going to be campy. Probably one of the silliest installments of the season, this one has camp for days. I love that Mrs. Howell (a GREAT character) is the target of the monkey’s desire, and there are some hysterically funny bits between the two. Also of note are the castaways attempts to lure the monkey out. So cheesy, but just undeniably riotous, and fun for Lovey lovers!

06) Episode 23: “How To Be A Hero” (Aired: 03/06/65)

The castaways try to cure Gilligan of his inferiority complex.

Written by Herbert Finn & Alan Dinehart | Directed by Tony Leader

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Here we have another episode with incredible heart, but also great humor — arising from the great coincidence that there just HAPPENS to be a headhunter on the island. In general, however, the first season (like Bewitched) had realer premises based more honestly on human foibles. This episode is a perfect example of such. But the series never loses its comedy and the show is funny throughout. Gilligan’s chase with the headhunter is particularly enjoyable.

07) Episode 25: “The Matchmaker” (Aired: 03/20/65)

Mrs. Howell tries to play matchmaker for Gilligan and Mary Ann.

Written by Joanna Lee | Directed by Tony Leader

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Believe it or not, this series has a rabid collection of fans who desperately wanted to see the castaways hook up. (Mary Ann/Professor, Ginger/Professor, and Mary Ann/Gilligan are the most common.) This installment should appeal particularly to the fans of the latter, as Mrs. Howell tries to hook them up. It’s actually VERY funny, and it gets even funnier when her matchmaking causes a rift between her and Thurston. Backus and Schafer shine!

08) Episode 32: “Physical Fatness” (Aired: 05/08/65)

When rescue looks imminent, Skipper tries to lose weight and Gilligan tries to gain weight.

Written by Herbert Finn & Alan Dinehart | Directed by Gary Nelson

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This funny episode has a wonderful setup typical of smart sitcoms — have two concurrent stories that are brilliantly connected thematically. (And it works because the stories are contained to the same locations.) Gilligan wants to gain weight while Skipper wants to lose his. To top off that hilarity, we have a rescue plan that is screwed up by Gilligan in a way that’s honest and builds upon itself naturally. This installment is a textbook example of Gilligan’s Island at its best — a rescue mission loused up by a personal predicament of which Gilligan is at the center. Superb.

09) Episode 34: “Goodbye, Old Paint” (Aired: 05/22/65)

The castaways try to convince a reclusive painter to return to civilization.

Written by David P. Harmon | Directed by Jack Arnold

Screen shot 2013-11-24 at 12.27.03 PM

This episode is another one of the funniest of the season. Dubov is such an obnoxiously hilarious guest star, and everyone is given moments to shine. I want to give particular mention to Tina Louise, whose scenes when she’s posing for Dubov and later when she sees the painting are both hilarious, and to Alan Hale, Jr., who, as always, is just sublime doing all of the physical stuff that he has to do. This is one of the best guest-star-oriented episodes of the series.

10) Episode 35: “My Fair Gilligan” (Aired: 06/05/65)

The Howells adopt Gilligan after he saves Mrs. Howell’s life.

Written by Joanne Lee | Directed by Tony Leader

Screen shot 2013-11-24 at 12.27.36 PM

I love episodes that center upon the Howells, and this one is no exception. Beyond great humor, however, we have real issues being explored about wealth and what it means in regards to happiness. Of course, we’re never forced to think about it too hard — everything for a laugh (as it should be). The dream sequence is cleverly appropriate to the action, and this episode boasts a smart script and (as usual) great performances.


As I mentioned above, there were many other episodes that I really enjoyed and considered putting on the list. Those include: “Home Sweet Hut,” the second episode of the series that answers some logistical questions and manages to be very funny, “Wrongway Feldman,” the first episode (which many fans seem to enjoy) that features a guest star — the divine Hans Conried, “President Gilligan,” which features a fascinating premise despite some illogical logistics, “The Big Gold Strike,” in which Howell is as greedy as ever and the castaways narrowly miss rescue, “Birds Gotta Fly, Fish Gotta Talk,” an ingenious clip show that uses material from the unaired pilot, “Three Million Dollars, More Or Less,” another episode that shines because of the greedy Howell, “Little Island, Big Gun,” which features a hilarious sequence in which the castaways dress up as natives while they’re being held hostage by a gangster, “Big Man On Little Stick,” in which the female castaways are particularly lustful, “Music Hath Charm,” in which the castaways hilariously and disastrously try to create an orchestra, “They’re Off And Running,” which features a simple premise but a strong script, “Three To Get Ready,” one of the first season’s most fantastical installments, and “Diogenes, Won’t You Please Go Home?” which is well written with a very intriguing premise.

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*** The MVE Award for the Best Episode from Season One of Gilligan’s Island goes to…..

“Physical Fatness”

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Come back next Tuesday for the best from Season Two! And tune in tomorrow for an all new Wildcard post!

5 thoughts on “The Ten Best GILLIGAN’S ISLAND Episodes of Season One

  1. Well, we disagree about the season’s best episode. I’d have to go with “Goodbye Island.” That whole bit of Gilligan and the Skipper getting themselves glued together and then stuck to the side of the poor S.S. Minnow cracks me up every time I see it. Not that I’ll argue much about it. “Physical Fatness” is a favorite of mine, too.

    One thing I’ll say about “Goodbye Island,” it always bugged my dad that the S.S. Minnow we see in that particular episode was obviously not the same S.S. Minnow we saw in other episodes. It was quite a bit smaller, for one thing.

    • I too love “Goodbye Island.” For my 12th birthday party, which was GILLIGAN’S ISLAND themed, I got the original script, and my theatre friends and I did a reenactment. The only hinderance, in my opinion, is that, as the second episode produced (following the pilot), both the production and the cast are still a little green. But, because of some truly hilarious gags, like the one you mentioned above, it may be my second or third favorite from Season One.

      Interestingly, “Physical Fatness” would never have been among my favorites if you’d asked me when I was watching the series while growing up. Now, watching every installment in order and studying them individually and collectively, I’m impressed with the episode’s ability to dovetail Skipper’s diet and Gilligan’s feasting with a ruined rescue mission. As far as storytelling goes, I really do think it’s the season’s smartest.

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  3. Good stuff. My fave is Big Man on a Little Stick just because every young man wishes he was Duke Williams being swooned over by Ginger and Mary Ann. Great choices I enjoyed it.

    • Hi, TShr! Thanks for reading and commenting.

      If you haven’t already, be sure to check out my picks for the best episodes from Seasons Two and Three!

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