Henry Elliott and his unnamed wife were two of the first guests to stay at the Castaways. Henry is the owner and manager of Henry Real Estate in Cleveland, Ohio with numerous deals and transactions going on at home. Together, they have three kids and two kids. His wife brings him to the island to relax, but he spends the entire time in a suit and obsessing on his business. At one point, he even sneaks off to the hidden telephone in the hotel resort to check up on his business. Gilligan and the Skipper trying taking him fishing, but he nearly drowns. The Professor takes him scuba diving, and while getting his massage from Ginger, he gets an idea to start an exercise studio in a warehouse back home. When his wife threatens to keep him on the island, Henry adopts a slovenly lifestyle to disgust her which backfires when she finds out his plan. Eventually, they come to a truce and Henry promises to work less.
- Henry was played by actor Tom Bosley of "Happy Days" fame; his wife was played by actress Marcia Wallace of "The Bob Newhart Show."