The Simpsons go to Cuba to get Grampa cheap medical care, since the retirement home and the V.A. hospital can't solve his health issues.
This is notable as being the final episode to be produced at Film Roman (having worked on the show since the fourth season in 1992) due to Waterman Entertainment buying out the studio. Beginning with the next episode, domestic production moves to FOX Television Animation.
- Bait-and-Switch Comment:
- Chief Wiggum expresses outrage at seeing an old man being abandoned at skid row because mentally challenged people are those that should be adandoned there.
- During the epilogue, Abe suggests that he and Homer could enjoy a golf match. The next scene shows them disturbing the players.
- The Cameo: Sideshow Bob is seen entering Cuba while Homer and a customs agent discuss the reasons people are legally allowed to visit Cuba for.
- Epic Fail: It took Rich Texan 12 years after he started digging for oil before he realized he should drill in Texas instead of New Hampshire.
- Gilligan Cut: Marge says the people at Springfield Retirement Castle will know what to do about Grandpa's incontinence. The next scene shows the receptionist saying they don't know.
- Global Ignorance:
- Homer and Abe decide to go to Cuba instead of Canada because they think Canada is the communist nation.
- One of the twelve legal reasons for people to visit Cuba is to mistake it for Aruba.
- Loophole Abuse: One of the twelve ways people are allowed to visit Cuba is being a journalist. Lisa gets the family in by showing her school newspaper article about Principal Skinner being arrested over a school stapler found at his house.
- Noodle Incident: Homer learned from a real estate deal that chewing your leg is not a yes.
- Properly Paranoid: During the trip to Cuba, Grampa won't try to get a tan because he's worried Homer will push him off the ship. Homer does think about doing it.
- Self-Deprecation: The chalkboard gag at the beginning of the episode which says "Being right sucks" is them making fun of their supposed prediction that Donald Trump would be elected president back in "Bart To The Future".
- The title is a pun on the 1965 movie Having a Wild Weekend starring the Dave Clark Five.
- The TV show Vulture's Nest is a parody of Dragon's Den.note Homer even mistakenly calls it "Shark Tank" once.