The Sky Crawlers

They both have the same director and are profoundly philosophical with existentialistic themes which is mirrored in the characters and the story in it's entirety.  

Aerial dogfights, lots of CGI. An unexplored setting with wars against unfamiliar foes. The story and characters are quite different though. 

Both are about life on military front lines with themes of dehumanization and prolonged conflict. In 86, the plot focuses on ground forces piloting spider tanks called Juggernauts. The titular 86 are forced to fight off autonomous drones to defend a nation that racially discriminates against them. There is a major theme of dehumanization expressed in their nation not recognizing them as humans even though they are, thus the Juggernauts are considered drones. As the story goes on, more is revealed about why the 86 have to continue fighting. In The Sky Crawlers, the plot focuses on a private air force made up of pilots who can't age, this private air force are sent to fight in the sky while citizens live in the comfort of their own city. With fighting looking like it never stops, the protagonist unravels a deep mystery about the nature of him and his fellow pilots. The daily lives on front line barracks of the Spearhead Squadron of 86 and the Kildren of The Sky Crawlers are fairly similar. read more 

The Sky Crawlers and Jin-Roh have very deep an intricate plots, drama, love, and of course talking. There are both great action scenes in both movies. Both movies are made by Production I.G., also, so they share a similar art style. (one little easter egg: there is actually a character in The Sky Crawlers named Jinroh) 

They may not have a very similar feel to one another, with The Sky Crawlers being more slow paced and philosophical, but both movies are visually stunning and are about pilots with great dogfights. 

Both anime deal with war. Both are about people that are not completely ordinary. What reminded me both extreme of the other were especially quotes concerning war. They both portray a similar moral.  

Both are about Flying Both have Air Combat Both are about the Main characters finding themselves Both are slowly drawn out Both have a lot of underlying subtexts that are never directly said. 

Both set in a not-so-distant reality you don't know much how it came to be. You may enjoy the similar mechanical technology design, although Wonderful Days' sky theme is backgrounded. Both have very good art and music and well placed CGI, one important difference to mention is that while one is focused on developing the characters the other is in reaching the story's climax. 

The Sky Crawlers and Area 88 are both anime that revolve around fighter pilots being forced to partake in a conflict. Looking deeper, they also share many things thematically: -in both anime the main character wrestles w/ the dilemma of fighting in a meaningless conflict -there are journalists present in both covering said conflict, not just how war is fought but how war is perceived -both have a unconventional conclusion, one which is neither happy nor sad but true to their respective themes -if you're into airplanes and flying, those sections of these anime are very well animated, especially the dogfights between the warplanes -both have some romantic subtext but no outright romance Some differences would be that the Area 88 OVA is a lot older. Area 88 also has a movie and television series versions, but from what I understand they're all similar and this recommendation extends to those iterations of Area 88 as well. In short if you enjoyed The Sky Crawlers you probably would also enjoy Area 88 and vice-versa.  read more 

Both movies have a great war plot and very immersive direction, even The Sky Crawlers having a more nihilistic and ''realistic'' look. The protagonist of both movies is also somewhat similar. 

While the plot and art style of Sky Crawlers and Cyberpunk: Edgerunners are pretty different, there are some similarities that really stand out. -No spoilers, but the way our main protagonist (Kannami/David) is built up to be this extraordinary individual, their-self realization, and their climatic meeting with the big bad (Teacher/Adam Smasher) and its result is almost identical in both. -the female protagonist in both (Kusanagi/Lucy) are pretty similar, initially appearing as this emotionless women, but later on revealing their aspirations/desires. -Both deal with some philosophical themes: what is the true purpose in life? What are we meant to be as humans? Whose dreams are we following? -pretty minor, but nearly every character in both anime smoke. If you enjoyed one, or at the very least want to experience sort of nihilistic feeling again, you'd might want to check out the other.  read more 

Although depicted in very different ways, these two present original perspectives of what can be related to the Buddhistic concept of Samsara and breaking the cycle of suffering.  

Some of the least anime-ish anime movies you can watch. It's paced and directed more like a live action film. 

Even though Memories are divided into three parts, if you like the heavy atmosphere and slow enfolding plot of The Sky Crawlers, I think you'll like at least the first and third stories of Memories. Both shows explore the meaning of existence and identity, even though The Sky Crawlers is a more depressing overall and Memories is more psychological. I would say the first story in Memories about a woman's unflinching grip over the past and her love is similar to the girl in The Sky Crawlers, but the other stories in Memories are definitely worth watching too.  

Another excellent angsty military aviation series but this time set in an alternative world with a WWII feel to it.  

Both anime feature child pilots who fly aircraft during a war in alternate universes. The Sky Crawlers is set in a world similar to ours with some differences. Simoun is set in a more fantasy-type world In The Sky Crawlers, the pilots stay as children for as long as they live, while in Simoun, the pilots can choose when they want to become adults. They both focus on drama and development, touching on philosophical and ethical issues related to the respective worlds that the characters of these two anime live in. 

Both films consist of minimalistic plots and the characters act in an emotionally subdued way. Although they differ in subject they still might cater to the same audience because of their similar atmosphere. Both movies have good visuals combining traditional animation with computer generated imagery. 

Both are similarly themed - adults using genetically altered children as soldiers.  

Airbase, romance and drama. 

These anime treat some of the same subjects. I feel that NHK ni Youkoso does a much better job though, as it does so in a far more entertaining manner. 

Both are extremely pretentious as far as the story goes, but somehow their animation and music forces you to sit through it. So maybe if you actually liked one of these, you'll also enjoy the other, considering I feel they have almost the exact same failures! 

Both have existential themes in a dystopic setting, slow plotlines and a similar ideological questioning about the nature of humanity.