Anime - Legend of the Galactic Heroes (OVA series, not Die Neue Thesis)
Reasons: The world building is extremely intricate, the majority of characters are very complex, the military tactics are better than anything else the anime medium has to offer (though there are manga with superior strategies and tactics due to the abundance of Three Kingdoms era adaptions) and the theme exploration of autocracy vs democracy, cults, human nature, history and personal philosophy are all explored wonderfully, as well as knows how to properly subvert expectations with proper foreshadowing when it comes to character deaths and such in a similar manner to The Sopranos or Game of Thrones' first four seasons. There's a reason why it's the go-to choice for many when it comes to describing the perfect anime, the only complaint many have that stands as valid being how the art style can sometimes change mid-scene due to all sources available being from the remastered DVDs, but that's pretty much a nitpick with how little it affects the work overall.
Manga - Ashita no Joe
Reasons: It's very much the antithesis of my complaints with most of the sports genre. There are actual stakes through the characters being in a limited financial position and the health risks boxing poses upon them, the protagonist has excellent development with him starting out as a selfish and brooding opportunist before gradually transitioning into a respectable hero and the rivalries between his three main opponents are all excellently done. Despite having a simplistic premise, it's a story with a lot of depth to it with it fully exploring the many aspects of boxing and its characters' motivations.
