There’s an entire genre of anime built around the concept of ‘what if I, a socially-isolated cynic who plays lots of videogames, were suddenly transported to another world that functioned more or less like a videogame?’ the genre is called isekai, and it’s responsible for some of the worst shows ever created. There’s one good one though, Re:Zero, which assumes its audience is familiar with this premise and then continues to steadily dismantle it, carefully attacking its protagonist Subaru’s toxic worldview. It’s also just a fundamentally solid show, complete with detailed world-building, a complex narrative, and excellent aesthetics. If you’re sick of isekai, maybe try just one more.
Re:Zero can be found on Crunchyroll.
The Monogatari Series
Starting with Bakemonogatari and continuing on forever, Monogatari asks the question “can we make an ecchi harem light-novel adaptation that’s actually good?” which is pretty much all you need to know about it. I would never recommend this sprawling series to someone just getting into anime: there are too many scantily-clad fanservice shots and incest jokes to ever explain away to a newcomer. However, there are some very compelling arguments about how Monogatari manages to make its lewd elements pull double-shifts to help tell its stories of trauma and self-loathing, and the core of the series is an incredible blend of experimental visuals and character arcs that are just genuinely good. Just make sure to use headphones for this one.
The Monogatari Series is scattered across the web. The complete first season (Bakemonogatari) can be found on Funimation, and most of the rest of it is on Crunchyroll. Crunchyroll also has Bakemonogatari, but it’s missing the last few episodes.
Kill La Kill
Kill La Kill is the worst show I’ll recommend, but I can’t pretend I don’t enjoy it. A heartfelt grab-bag of anime tropes with clever writing, Kill La Kill lacks coherent direction and purpose but it sure is fun. Featuring mechas, magical girl transformations, high school as the battleground for intergalactic war, elite fours, tournament arcs, and way too much stripping, Kill La Kill is what would happen if you took all the trashy seasonal shows and threw them in a blender with some vodka. It can be a great time if you don’t look too closely and know when to zone out.
Kill La Kill can be found on Crunchyroll, Netflix, and Hulu.
Made by the same team as Kill La Kill while working for a different studio, Gurren Lagann holds the advantage over its younger sibling of having a coherent story and cleanly executed themes. It’s very much a love-letter to giant robot shows of all shapes and sizes though, so before embarking on the Biggest Adventure Ever with Simon and co I’d recommend having at least dabbled in some giant robot anime. They aren’t too hard to find, I promise. You can still enjoy the show going in without the cultural touchstones, but there’s some genre-savvy short-cutting here that assumes a certain level of familiarity with the general anime process of acquiring and getting inside a large combat machine.
Gurren Lagann can be found on Crunchyroll, Netflix, and Hulu.