Combine your average Isekai fun with the dread of Majora’s Mask and the psychological rattling of Doki Doki Literature Club.
How Not to Summon a Demon Lord
If you don’t want to admit to yourself that you really just want to watch hentai, go ahead and watch this. Otherwise, your eyes are going to be doing 300 RPM in your sockets, both for rolling because it’s so dumb and for checking to make sure nobody sees you watching this trash.
Overlord (Seasons 1-3)
A fun and good watch but a bit lacking in direction.
Saga of Tanya the Evil: The Movie
Everything good from the series and then some. Better pacing, better action, more of the introspection and question asking.
Saga of Tanya the Evil (Youjo Senki)
Stellar military piece with fascinating philosophical aspects. Makes you inspect your stance on national policy, patriotism, war, social Darwinism, and capitalism.
Sword Art Online (Season 1)
A fantastically immersive love-letter to MMORPGs backed with strong emotion that makes a great Gateway Anime. Then it goes sideways for the second arc before picking up the pieces for its second season.
KonoSuba: God’s Blessing on This Wonderful World!
The pinnacle of well executed and clever stupid comedy. Strongly channels the vibe of if a group of stupid friends got together to play D&D, and one of those idiots is the DM.
.hack//SIGN
While it is perhaps the seminal "trapped in a game" isekai, the pacing of this was so painfully slow. While the soundtrack is a masterpiece by Yuki Kajiura, it's used so awkwardly and repetitively that it doesn't do it justice. Skip this one.