IMPOSSIBLE QUESTION. THERE ARE TWENTY YEARS OF MUSIC HERE AND I KNOW TOO MUCH OF THE LORE. I AM NOT ALLOWED TO HAVE FAVORITES. I WILL SIMPLY WALK INTO THE RADIO ROOM AND COMBUST.
joking, but. wow this is ABSOLUTELY the hardest band to answer that question for! so I'm gonna cheat and flaunt the 5-thing constraint, and pick a favorite from each "main" record. I'm not counting TCAA since the Falling Up name is, as I understand it, there for visibility and "bridging the gap", so to speak.
From Crashings: gonna be honest, "Escalates" is the only one I can handle listening to anymore. I've always had really complex feelings about that record, and Jessy's audio history podcast (very worth the time!) made all of those feelings make a LOT more sense. I own a copy, but it just kinda sits on the shelf.
From Dawn Escapes: "Exit Calypsan", but only because I constantly meme about the fact that we have FOUR versions of it now, and that Jessy keeps sneaking that piano line into different stuff and expecting us to believe him when he says they're not related. This is one of the reasons I have a corkboard.
From Captiva: I think, given the thing that happened during the Reimagined livestream, my answer is contractually required to be "Helicopters", actually. Someone in the discord called me "the Helicopters guy". I don't think I'm allowed to say it's "Captiva" anymore.
From Fangs!: "Magician Reversed". It's one of my favorite narrative Falling Up songs, and the symbolism of that particular tarot card is so well woven through its fabric (album lore pun intended).
From Your Sparkling Death Cometh: "The Light Beam Rider". My most-played by a long shot, and I am on record as telling Jessy that if I had to pick an all-time favorite, it would be this one. Suffice it to say, I could and should write a whole essay on this one alone.
From Hours: ....This is the worst one for me because I love this record to bits. It is the most insane thing these guys have ever done. What do you MEAN they wrote and recorded each of those songs in a week or less. Anyway I'm gonna have to say "The Outsider" by default since I covered it once. (I'd like to finish that recording eventually.) "Aeva and the Waving World" is a close second, I often play them back to back.
Honorable mention from Midnight On Earthship, even though I consider it a "bonus" record: "Who You Are". I held onto that one with a white-knuckled fist as a genderqueer teenager, and it's so so important to me.
From the self-titled: Again. Whole record rips. I listen to it all the way through routinely. But it's gotta be "Rangers". Complex time signature, another fantastic narrative song... and it's about the narrator committing arson. It is so incredibly unhinged in the best way.
Honorable mention: "Circadian" is probably my favorite from a music theory perspective, because it uses 3/4 in the verses and 6/4+7/4 in the chorus, which is beautifully insane. It gets stuck in my head constantly, and I've been known to loop it and the "Evidence" rework back to back many times.