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There are so many isekai series out there I don't know where to start... I'll name a few older ones to begin with.
The Vision of Escaflowne (Sunrise, 1996) - The series follows a teenage high school girl named Hitomi, who finds herself pulled from Earth to the planet Gaea when a boy named Van appears on the high school track while battling a dragon. In Gaea, she is caught in the middle of a war as the Zaibach Empire attempts to take over Gaea.
Recommended because: I watched it for the first time a few years ago and it wasn't very impressive. But it was very popular about 15 years ago and a big part of older anime fans' psyches. You've probably heard of it, so you might as well try it and see what the fuss is about.
Unlike most recent isekai, the main character is female and not overpowered at all, so it's also good to try if you're tired of the standard formula.
El-Hazard (AIC, 1995) - An anime franchise that focuses on three high school students and their history teacher who are mysteriously transported to the fantastical world of El-Hazard. El-Hazard is threatened by a possible war between the human nations and the insectoid Bugrom tribe.
Recommended because: It's a long franchise with several installments, so it's good if you want to immerse yourself fully in another world. It's also good if you like retro anime art. I've only watched one episode so I can't comment on the quality, but by all accounts it's quite watchable.
Now and Then, Here and There (AIC, 1999) - Follows a young boy named Shuzo "Shu" Matsutani who, in an attempt to save an unknown girl, is transported to another world which is implied to be the Earth in the far future. The world is desolate and militarized, and water is a scarce commodity.
Recommended because: It's a grittier, more realistic take on the usual "plucky boy goes to another world." What would really happen if an ordinary boy was dropped in the middle of a war in a civilization that uses child soldiers like they were tissue paper? The results are extremely grim and some would say over-the-top, but it's a good watch if you want something completely different from the usual idealistic isekai. It's also short at 13 episodes and a complete experience so there's no need to read any mangas or light novels to get the full story.
Twelve Kingdoms (Juuni Kokki) (Studio Pierrot, 2002) - The Twelve Kingdoms is a series of novels that focus on a world inspired by Chinese mythology, where twelve different kingdoms exist under the rule of an individual chosen by the Tians. One of the major stories of the series centers around a red-haired girl named Youko Nakajima from Japan who is suddenly transported to the world of the Twelve Kingdoms and searches for her destiny.
Recommended because - Twelve Kingdoms has very interesting world-building. It's good if you like to learn about other-world politics, society, economics, etc. Youko's growth from shrinking violet to powerful character is frustrating to watch but satisfying in the end. The show also deals with the struggles normal characters would have with things like language and acceptance, it's not all roses and wine. The anime series completes Youko's arc but some other threads remain unresolved.
Fushigi Yuugi (Studio Pierrot, 1995) - Tells the story of two teenaged girls, Miaka and Yui, who are pulled into The Universe of the Four Gods, a mysterious book at the National Library. Main character Miaka is destined to gather the seven Celestial Warriors of the god Suzaku in order to summon Suzaku and obtain three wishes.
Recommended because: Like Escaflowne it's part of the anime consciousness, especially for shoujo fans. There aren't that many shoujo isekai anime and certainly none this popular so it might be worth a watch if you're a shoujo fan. The main caution is that the girls are really annoying. Like, really. Seriously. Miaka! Tamahome! Miaka! Tamahome! I only read the manga and I was sick of them by the end.
Magic Knight Rayearth (Tokyo Movie Shinsha, 1994) The series follows three eighth-grade girls who find themselves transported from modern-day Japan into a magical world, where they are tasked with rescuing a princess.
Recommended because: I don't know of many isekai magical girl shows, so this might be your only option if you like those two genres. As with El-Hazard I've only tried one episode but it has its fair share of fans and apparently sold 200,000 copies for the US version of the manga. The manga is only 6 volumes long but the anime has 49 episodes so expect a fair bit of filling and padding.
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