A sideways tribute to David Foster Wallace, and an amazing episode
So: first things first. I think the episode title probably threw a lot of people. It's a reference to a long essay by now-deceased American genius author David Foster Wallace. In his essay, Wallace - an extremely neurotic fellow - goes on a luxury cruise. He finds its luxury unsettling, off-putting, and ultimately corrosive to the human soul.
Wallace concludes that the luxury of a cruise just leads to hedonic habituation. After a few days the luxury stops seeming "amazing" and starts feeling "obligatory," so you find yourself genuinely complaining over the fact that you were only able to go back to the shrimp bar three times at dinner before they ran out of shrimp (or whatever), as if that was a thing that really mattered.
Now. Our episode begins with a sequence illustrating Bart's ennui with everyday life. (This sequence is incredible, I had to watch it several more times on YouTube just to get the full effect. The song is "Boy From School" by Hot Chip.) Bart becomes convinced that a luxury cruise is just the thing to break the Simpsons out of their day-to-day rut.
They scrape together enough money for a super-economy room, but are bumped up to super-luxury. And unlike David Foster Wallace, they think it's the best thing ever! (Cue second incredible sequence of the episode, where a stylized Bart scampers through the ship enjoying all it has to offer.)
They enjoy it so much, in fact, that Bart decides to fix it so that they will be on that cruise forever. But it turns out that the joys of the cruise were just a temporary artificial bubble created by the cruise ship company. The way Bart engineers their permanent cruise also pops that bubble, and all of humanity's ugliness comes rushing forward.
In the end, the Simpsons are unceremoniously dumped on Antarctica. Where they learn that you can have fun just by living in the moment and enjoying what you've got, like the penguins. It doesn't make much logical sense (shouldn't they at least be wearing long-sleeved shirts?) but thematically, it's a perfect ending. (Speaking of the ending, it featured "Winter's Love" by Animal Collective.)
Some reviewers claim to have spotted a David Foster Wallace stand-in, wearing a tuxedo t-shirt. I missed it, but I'll be looking carefully the next time I watch the episode. Sadly, this literary genius committed suicide in 2008.