Despite eschewing a lot of the tired story structures of the past, season 7 has several familiar tropes of its own. It's heavily reliant on externally driven stories where a main character is troubled by some external force, and many of these stories are written heavily to theme to the point of tedium. However, these formulas don't always ruin their stories, and many episodes transcended those tropes, either with nuance ("The Perfect Pear") or humour ("Parental Glideance").
"Once Upon a Zeppelin" is still a little on-the-nose, and its conflict still has too many external actors, but it's the best example yet of how good jokes and a good moral can overcome smaller issues. It's another contender for the funniest episode this season, packed with sharp character-based humour while also giving more personality to Shining Armour and Twilight's parents. Further, it's one of the few episodes to actually explore how Twilight's new responsibilities affect her usual anxieties, and although it's a bit blunt, the moral of learning to draw boundaries is a rock solid complement for "A Health of Information."
When Twilight's parents win a free zeppelin cruise, she's naturally suspicious, but decides to play along. However, when the family - including Shining Armour and Princess Cadance - arrive, they're shocked to discover that the main attraction of the cruise is none other than themselves, as run by Iron Will. Twilight, wanting to give her family the best vacation possible, agrees to play along with Iron Will's plans, and in doing so, forgets to enjoy herself.
If there's one thing I must give season 7 credit for, it's making the mane six's families utterly delightful. As was the case with Rainbow Dash's folks, Twilight's family is endearing and hilarious: her father Night Light is apparently a bingo enthusiast, and her mother Twilight Velvet has a major adventurous streak. Meanwhile, Shining Armour is given more traits, such as a fondness for small things and a tendency towards airsickness. Unfortunately, Cadance is reduced to just being a mother, and while the episode does its best to maintain her lovable sweetness, it only makes me wish more for her to have a chance to shine away from the family.
Best of all is Twilight, in yet another phenomenal season 7 role. One thing I've wanted from her since season 4 is some indication that she struggles with the responsibilities of being a princess, as her stressful personality and high self-expectations have always been a large part of what makes her so relatable to me. "A Flurry of Emotions" was the first episode to directly address the expectations that being a princess gives her, and "Once Upon a Zeppelin" makes them even more explicit while even making them relatable. Here, Twilight specifically mentions that she "needs to make the cruise ponies happy ... to be a good princess," finally addressing something the show has implied for years now.
While Season 4 also attempted to feature Twilight struggling with being a princess, but there it was so abstract that it was hard to relate to. Here, Twilight's anxieties are directly linked to trying to make others happy, which does a lot to humanize her. She wants her family to have the best vacation possible, even if it means she needs to sacrifice her own happiness. Everyone who cares about her tries to convince her to take a break, but she's too afraid that it would mean she fails those around her. To some extent, this moral about taking care of yourself as well as others is a repeat of "A Health of Information," but it's given freshness by the context and an emphasis on drawing boundaries.
While on the ship, a young stallion named Star Tracker wins a raffle which allows him to spend the cruise as an honorary member of Twilight's family. This character is one of the show's most impressive examples of condensed character development, as while he almost exclusively exists through a handful of sight gags, it's immediately apparent from his demeanour that he has difficulty with social interactions and may even have a small degree of social anxiety. Some of the ways this manifests are creepy enough to make him less endearing, but for the most part there's some real charm in his awkwardness.
As a result, when he finally stands up to Iron Will at the end in defense of Twilight and her family, it's satisfying to see him get over this to protect ponies who have been nice to him, especially when he's committed a few social faux pas towards them. Similarly, although there's some catharsis to be found when Twilight finally snaps at him, it's also satisfying when she apologizes and even allows him to continue hanging out with the family. And all of this is despite his dialogue consisting overwhelmingly of stammering, often for no more than a couple seconds per scene.
In fact, despite my complaints about Cadance, she too shines best in the ending, where she's given the opportunity to comfort Twilight and give some advice. I still wish the show would grant her a little more nuance, and the speech still has too much to do with Cadance's role as a mother, but it's still wonderful to see these sisters-in-law bonding, which we haven't really seen since season 4. Similarly, when Twilight's family finally tries to make up for all the fun they had without her, it's really charming to see how much they really do care.
Iron Will is the captain of the zeppelin, and he's just as hilarious here as he was back in season 2. As an antagonist, he has the unique appeal of keeping his villainy entirely legal while still somewhat skeevy. He's particularly fond of covering his tracks with contracts he knows nobody will read, and this means that no matter what he pulls, he can always get away with it. This is particularly welcome, because his boisterous personality is an absolute delight here, and he has many of the episode's best gags, so knowing he can always come back is hugely promising.
The real humour just comes from the great timing and script, though. At one point, Iron Will tours completely random locations while making up princess-related details about them. At another, Shining completely fails to participate in an on-deck jet ski race because his airsickness is bothering him. This episode is packed with even more great jokes than the already delightful likes of "A Flurry of Emotions" or "A Health of Information," and might even be the funniest of the lot.
"Once Upon a Zeppelin" is a last-minute delight which combines the two things season 7 excels at: new family characters and Twilight Sparkle. With a great moral about drawing boundaries, some of Twilight's best characterization in years, and a consistently hilarious script, this is easily one of the season's best episodes. Plot-wise, it still sticks a bit too closely to theme, but it's also just so filled with humour and joy that I find it utterly irresistible, and combined with all those other admirable qualities, it's an episode which I have no hesitation about adoring.