We've got very different tastes, but hey maybe you might want to give some of these a try:
- Air - already in your PTW list, but just gonna put this on here so that you watch it ASAP. not as humorous as Angel Beats, but as Key worked on both of these, the humor that is present here definitely has its moments and might remind you of that show.
- Ojamajo Doremi - airing at the perfect criteria you're looking for (this series began in 1999 and ended in 2000, though there are more seasons after this), this is a show about three human girls and their daily lives while they become witch apprentices and work part-time at a magic shop. this may be a children's show, but don't overlook it because of that fact—if you want something that has serious heart and tackles heavy topics well, you will want to give this show a shot.
- Princess Tutu - if Ojamajo Doremi is a bit too girly or kiddie for your liking, then check out another anime that the director of that show also directed—this one's got a bit of a weird (but definitely unique) premise about a girl who not only isn't actually human, but can turn into a ballerina named Princess Tutu, who has to collect shards of a prince's heart. if you want something unique and with hidden depth to its story, give this one a shot—there's a reason why this anime's kinda considered a cult classic on the internet (if you don't believe me, you can always read how a 4chan anon described this anime... it's pretty spoilery though)
- Prétear: The New Legend of Snow White - oh look, what do you know, another early 2000s magical girl anime directed by the same director as the past two entries here—in fact, that same director actually created this series. this is essentially an anime that takes the story of Snow White, but cleverly twists it into a magical girl anime with a big focus on character development and drama. if you're really into those two aspects, you'll probably like this anime and the aforementioned Princess Tutu a lot.
- Uta Kata - here's another magical girl anime that is similarly dark than the past two entries here, but is definitely way more darker (recommendations between this anime and Puella Magi Madoka Magica are not uncommon here). unlike most other magical girl anime that either focus on becoming a good girl or fighting evil, this is an anime that uses pretty visuals and great music/OP/ED to hide its true nature of being a psychological coming-of-age story. if you really like stories like that, you should definitely give this anime a shot—it's pretty underrated in my opinion.
- Twin Spica - this is a (loosely) sci-fi anime based off of one of my favorite manga of all time. it has mentions of space and takes place in a space school, but otherwise feels like a realistic seinen slice-of-life story with a couple of feels here and there. i haven't finished the anime but i really want to finish it—you should give this a shot too if you want something more down-to-earth.
- Azumanga Daioh - ...ooookay here, to lighten things up, i'll end this list with a comedy recommendation. this anime is really really funny and if you wanted something like lucky star, but with more going on and with less of the otaku stuff and more of the crazy comedy hijinks, go ahead and give this a shot. that's all i can really say to sell you on this, just go and watch it lol
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