Honestly, "recs" were my first thought at a prompt of "entertaining". Specifically, I'm highlighting these works not because they're especially deep or anything like that--though one is--but because they have a sense of humor that makes reading/viewing them a delight.

1. [FANVIDEO] Waking Up In Vegas Wall Market
Rating: PG
Length: 3:26
A Cloud & Aerith cosplay video done to the song "Waking Up In Vegas". The scenarios of their antics are for the most part hilarious--and then there's a few preciously sweet moments for those who like the Cloud/Aerith ship.

2. [FANCOMIC] FF7 Comic by on deviantArt
Rating: T
This is a long, long-running series--over 300 pages, and not even bumping off Aerith yet, though foreshadowing her death is one of the jokes that pops up, along with plenty of humor about how her lines (and others') were translated. A lot of the fun of the comic is celebrating how much FFVII is loved in spite of all the little moments that make no sense. The comic starts here.

3. [FANFIC] The Answer by MillieBee on AO3 [ Fanfiction.net copy here ]
Rating: T
Length: 42,151 words.
The "incidentally deep" rec, though its depth only becomes apparent after a lot of zaniness. Cloud time travels back to when he was 14, and all because he was being stupidly curious and messing with a materia machine. He immediately resolves to change the future, and as one of his steps to do so...joins Reno and Zack's drinking night? It makes sense in context, because the context is crack humor and characterization, with increasing moments of heartfelt seriousness as the date he's working hardest to change, the Nibelheim incident, draws closer and closer.