1. Chapter 3 - Playing through this chapter as an 8-year-old kid has to be one of my most nostalgic early gaming memories. Everything about this chapter works -- the colorful cast of characters, the focus on TTYD's excellent combat system and the imposed restrictions by Grubba, the central mystery (I vividly remember the jingle that would play when "X" messaged you creeping me out), the miniboss and boss fight, and even the way that NPCs drip-feed eerie lore about the locker rooms, only for you to have to experience all of that lore yourself on your way to the Pit at the end of the chapter. I remember being genuinely concerned for the characters' safety in this chapter. Phenomenal gaming experience.
2. Chapter 6 - I'm SO curious how this one stacks up after I replay the game this year. The Excess Express is a hilarious, charming, creative experience the first go-around, but I can't deny that a lot of its magic lies in the initial playthrough, when you're going in blind. The chapter is so light on combat and heavy on text/characters/intrigue that I'm eager to see if I'm just going through the motions after I replay it for the first time in 8 years. That said, I adored this chapter as a kid, the pit stop in the middle at the train station is a great way to break up the monotony, and Smorg is a pretty terrific, challenging boss if you aren't careful. I also love that the chapter ends with an unconventional, no-boss Crystal Star pickup.
3. Chapter 8 - Everything about the finale bangs, imo. The Palace of Shadow is a fun gauntlet, Riddle Tower is clever and mysterious with wonderful ambiance, and the way it incorporates every main antagonist into a gauntlet of sorts at the midpoint and endgame is ingenious. Seriously, the sirens, Gloomtail, Grodus, Bowser and Kammy, AND the Shadow Queen, who is head and shoulders above every other mandatory boss in the game?! Straight fire. And the reprisal of the opening storybook musical motif gets the emotions going every time as everyone wishes for Mario and his pals to win.
4. Chapter 4 - Obviously a divisive chapter, and I'm really split between this and Chapter 5 for the fourth slot, but I think the sheer ingenuity of Chapter 4 and the unparalleled atmosphere puts it a step above...at least for now. Sure, Doopliss is too easy the 2nd go-around (I wish he had like 60-70 HP instead of 40 and the enemy partners did more damage) but this was one of my favorite chapters as a kid, when I was less observant of backtracking.
5. Chapter 5 - It feels truly crazy putting 5 this low. Bobbery's origin, Pirate's Grotto, Cortez' boss fight, and allying with Cortez against the X-Nauts is all easy S-tier. So is Flavio. So why might this only be an A for me? I just don't enjoy that much of the chapter's first half. I think it's unevenly paced, with another spot of iffy backtracking while also being the most 1:1 translation from PM64's equivalent chapter to this one, so it doesn't feel quite as inspired to me as other chapters here. The highs are euphoric though, and Cortez probably has my favorite design of any boss in TTYD.
6. Chapter 1 - Hooktail Castle is a perfectly solid opening "dungeon", and the ability to intentionally make the Hooktail fight harder on yourself is a liberating option to have on repeat playthroughs. The introduction of Ms. Mowz is fun, but ultimately, this chapter is fairly bog standard as far as Chapter 1s go. The Koopa Bros from 64 > Hooktail.
7. Chapter 7 - Despite having one of the biggest bops in the entire game during the X-Naut Fortress segment, much of this chapter is a slog. Everyone knows about General White's BS for a reason, and even the moon isn't fun to navigate until you get to the X-Naut Fortress. Worse yet, they re-use the worst boss in the game here...just with a few extra bells and whistles.
8. Chapter 2 - The punies are cute, and Boggly Woods is one of the areas I'm actually most excited to see remastered with that beautifully serene music, but yeah, the Boggly Tree just isn't for me. And I love Pikmin! But unless the remake massively improves the AI or finicky nature of navigating through the tree with your Punies in tow, I can still see this ranking as my least favorite TTYD chapter. But hey, it introduces the Sirens in combat, so it gets points there!