The 5 Funniest Mistakes That Made It Into Gilligan’s Island

“Gilligan’s Island” is a fun show about a group of castaways who never seem to get rescued despite nigh-weekly opportunities to make their way back to civilization. It’s a premise that requires a certain suspension of disbelief from the get-go, especially by the time you witness the other castaways forgive Gilligan (Bob Denver) for sabotaging their attempts to secure a rescue for the umpteenth time.

However, there’s a reason the CBS show is a classic. It carries a rare charm that’s able to lull the viewer into said disbelief so easily that whenever you watch the show, it’s hard to resist going with the flow from the second you hear that infinitely catchy theme song. This ability to casually sweep the viewer away for 25 minutes of desert island levity helped “Gilligan’s Island” become one of the best TV shows of the 1960s, despite the fact that it contains some truly hilarious mistakes.

Many of these gaffes are, of course, simple cases of production oversight from the makers of a silly little 1960s comedy show who had no way of knowing what a multigenerational syndicated juggernaut their creation would eventually become. Still, considering the sizable plot of pop culture real estate that “Gilligan’s Island” occupies, they’re well worth pointing out. Here are five of the funniest mistakes that made it into “Gilligan’s Island.”

“Gilligan’s Island” plays famously fast and loose with the horrors of getting stranded on a remote island. Strange visitors turn up on a nigh-weekly basis, and even the pilot episode’s original castaways included two very different characters from the ones we know — namely, two flat characters called Ginger (Kit Smythe) and Bunny (Nancy McCarthy). The former, of course, soon became the film star figure Tina Louise made famous, and the latter was replaced by Dawn Welsh’s Mary Ann. However, the show’s opening credits include another, more peculiar character mystery that never really gets resolved.

When the opening sequence shows the S.S. Minnow sailing into its sitcom doom, we clearly see all seven of the show’s soon-to-be-shipwrecked main characters in various parts of the boat. The five guests are clearly at the bow and stern of the ship, while the Skipper (Alan Hale Jr.) and Gilligan (Bob Denver) can be seen lounging on the observation deck atop the cockpit. So … who, exactly, is the eighth figure steering the boat?

The idea of positioning all the members of the main cast in various prominent locations aboard the boat and having another person steer the ship makes sense — after all, you don’t want to cause unnecessary risk by putting any of the actors behind the wheel. Still, since there are eight people visible aboard the S.S. Minnow at this point and only seven make it through the storm to the island, this adds an eerie undertone to the show’s otherwise cheery opening.

One of the many, many schemes the castaways of “Gilligan’s Island” hatch to get back to civilization is the U.S. Air Force jet pack that washes ashore in season 3 episode 27, “It’s a Bird, It’s a Plane.” The person who ends up flying the thing is Gilligan, who wastes most of the device’s fuel deposits on an accidental test flight over the island, blunders the Professor’s (Russell Johnson) well-designed rescue mission, and finally loses the pack entirely … which is a shame, considering that the Professor actually manages to figure out how to make more rocket fuel for the thing.

It’s actually strange that Gilligan fails to get the group any help with the jet pack, considering its seemingly impressive operational range. In fact, when the viewer sees him soaring over the landscape, he’s very noticeably flying over a hardwood forest that looks nothing like the tropical jungle vegetation of the island. The dramatic scenery change happens immediately after Gilligan takes off — mere seconds after he’s seen standing beside the Professor and the Skipper.

No one expects a show like “Gilligan’s Island” to go full “The Rocketeer” for a jet pack gag, so it’s understandable that the brief moment we see Gilligan flying isn’t particular about the scenery it’s using. Even so, witnessing Gilligan fly over a completely different growth zone makes one wonder why he doesn’t just land and ask for help from the next person he sees, since he’s clearly not on the island anymore. It also commands respect for the show’s version of the Air Force, which has managed to create one heck of a flying device.

There are two key elements to the plight of the “Gilligan’s Island” castaways: Gilligan’s ineptitude that often prevents the characters from being rescued, and the comfy but irreparable S.S. Minnow. While little can be done to the former, keen-eyed viewers may observe that the poor boat is surprisingly mobile for a marooned marine vessel.

If you pay close attention to the various shots of the S.S. Minnow over the course of the show’s first season, you’ll notice that the boat moves quite a bit from its initial, beached resting place by a huge palm tree. However, as the season progresses, the massive palm tree by the boat mysteriously disappears, while other trees randomly appear. What’s more, season 2 moves the Minnow to a far smaller stretch of beach where it’s surrounded by trees and nearly touches the water, tinkering with the boat’s design while it’s at it.

The way the Minnow teleports from its original barren location to a more eye-popping one makes sense from a production standpoint, seeing as this new, colorful beach made its debut when the show started filming in color. Still, the other apparent changes in its season 1 location go unexplained, so it’s fun to imagine that the castaways just randomly haul the boat from place to place to stave off boredom.

“Gilligan’s Island” season 3, episode 15 is called “Gilligan Goes Gung-Ho,” and explores the castaways’ quest to create a law enforcement office in their tiny community. The attempt is, of course, doomed because Gilligan ends up acting as a deputy and locks everyone — including himself — in a makeshift jail after a series of mishaps. This turns out to be a characteristically disastrous decision when a plane passes over the island while the group is locked away in the cave prison. After realizing what just happened, the terrified Gilligan escapes the inevitable admonishment by running straight through the bamboo cell door.

The cartoonish scene clearly doesn’t go quite as planned, as Gilligan’s hat falls off his head as he runs through the door. However, when the scene switches angles mid-run to show Gilligan’s rapidly disappearing back, the iconic white hat is firmly pressed on his head. What really makes the moment is Bob Denver very conspicuously bringing a hand on his head after bursting through the door and realizing that he’s left his headwear behind, only to magically wear it again a fraction of a second later. In all likelihood, the makers of the series simply didn’t have spare doors for Gilligan to burst through, which led to this fun little mistake making it into the finished product.

“Gilligan’s Island” is very open about the fact that Gilligan isn’t the marrying type. On the contrary, he’s a deeply immature guy who’s incredibly wary around women at the best of times, and makes clear his intentions to stay single. However, unlike his “Gilligan’s Island” character — who’s consistently portrayed as an innocent (if occasionally mischievous) and childlike figure — Bob Denver was married for no less than four times.

In one memorable occasion, Denver’s real-life wedding ring ends up creating a confusing moment for the relationship-averse character. In the turtle-themed season 1, episode 28, “They’re Off and Running,” Gilligan can sometimes be seen sporting a very noticeable wedding band on his ring finger — an out-of-character moment, to say the least. While it’s a minor oversight, seeing a wedding ring on Gilligan is particularly amusing when you consider the character’s awkward nature and vocal anti-marriage stance.