I listened to all the entries and I enjoyed every single one!
...but everyone loves feeling validated by a stranger online so here my personal top three, your egos are welcome!

#3 - In The Middle by Garbage Cat
Chiptune automatically evokes nostalgia for me but this one gave me the happy-sads on multiple levels. 

#2 - Icon by Talen Bartlett
I love how this almost completely changes tone about a third of the way through. I especially love the baseline in the latter parts of the song which had my body involuntarily moving.

#1 - Single Step by festervaunt
This song feels like its in a completely different league, which is even more sickening when reading this is their first time writing for a Gameboy. This disgusting display of talent deserves nothing but adoration, that is all.

Honourable mentions:

8 Bits Never Did Us Wrong by NostalgicStory - For best chiptune jungle i've ever heard (though currently the only contender)

Dungeon Level by StrangeStrains -  For best game-less game soundtrack.

Feel the Gr00v3 by mars_rulez - Because i did and it does!

Garsh, my ego does thank you! It was an honor just to finish a song. I’ll pay it forward with my own top three:

• PENDULATION by eskur: I love all the wobbliness everywhere. If this is “rough”, I’d love to see the final mix!
• In The Middle by GarbageCat: If this song were in a police lineup with actual GB soundtracks from the 90s, and I were asked to identify the one not written 30 years ago, there’s just no way. You totally nailed the aesthetic; great job!
• I Wonder Where We Were: This song kept me on my toes the whole way through, constantly adding new elements and iterating on old ones while maintaining a cohesive identity throughout. As somebody who can’t seem to just let a song settle into a comfortable groove, this is the sort of thing I aspire to write. Game(boy) recognize Game(boy).