A Totally Fun Thing That Bart Will Never Do Again (S23, E19-505)

...and with that, the Simpsons have now visited every continent.

Plot Summary
Bart's life has become the model of boring tedium.  His spirits start to rise when he sees a commercial for a luxurious cruise ship vacation, and decides he needs to go on there to finally have some fun.  Of course, nobody in the family can afford such a thing so Bart decides to get money by pawning all of his stuff.  He only gets half of what he needs, but the family sees Bart's dedication to the cruise and they decide to sell a few things as well to get Bart the remaining money for the cruise.

Thanks to some luck, the family ends up in a rather superb cabin during their cruise, and Bart is more than prepared to have the utmost of fun.  Lisa makes some great new friends in an elite kids zone, and Homer and Marge have more fun together than they've had in years.  Bart takes notice of this, and is happy that everyone is having so much fun on the cruise, especially him.  However, a song the cruise director sings makes Bart come to a devastating realization: this fun is going to end, and soon his life will return to the boring dredge it was before the cruise.  Imagining his old, dying self reflecting on his boring, wasted life, Bart decides to take matters into his own hands, finding a way to the rig the cruise's video systems to make everyone on it believe that there's a worldwide pandemic, and that they must stay in the cruise indefinitely.  Bart also destroys the ship's communication systems to ensure the vacation lasts indefinitely.

Twelve days later, the cruise has devolved to something that pretty much isn't "fun".  Bart tries to have fun still, but neither Lisa nor his parents are having any fun now because of the supposed pandemic.  Marge and Lisa figure out what Bart did, though, and force him to tell the cruise director of his trick.  Everyone in the cruise becomes so upset over being fooled like that, they drop the entire family off in Antarctica (where the cruise was now heading to repopulate mankind) as some sort of vengeance against them even though Bart acted alone.

Bart is able to stop the family from being super mad at him by telling them that he was only trying to extend their happy vacations as well.  Nearby, the family sees a group of penguins doing their thing.  Bart laments that the babies will only grow up and do the some mundane things their parents are doing, but Lisa tells Bart that at least in the meantime the penguins know how to have fun, and that its because of those 'in the moment' bursts of fun that life becomes worth living.  Bart takes heed, and the family joins the penguins in their fun activity of sliding around in Antarctica, eventually returning home at some point somehow.  Now, and older, maybe dying Bart reflects on his life and doesn't reflect on the boring parts, but moreso the fun things he did from time to time, and the old man comes to reflect well on the life he lived.

Quick Review
This episode really had a good emotional element to it, albeit it didn't really sneak in until at the very end when it goes back to old Bart again, and it really does a decent job of making up for the episode's primary problem: it just wasn't funny.

Final Score: 6.8