Super Mario Galaxy 2?

So all games were guessed already until now. Some new ones;

21 - I guess they couldn't really model his... thing, and couldn't really program a... stream, so the guy's just standing there.

20 - Some Magic Potion here, some Magic Potion there.

Could #21 be GoldenEye? Thinking of the bathroom in Facility.

I agree. Back when it first got released, I remember disliking the whole time limit angle. It made me feel rushed and thus discouraged from exploring, which has always been among the Legend of Zelda's top sources of appeal to me. But I played it again more recently -- inspired by Evan's Legend of Zelda Replay series here on VG Chartz -- and wow! Where Ocarina of Time for me has begun to show its age a little, with so many other games having reused and expanded upon its key ingredients over the years, Majora's Mask now stands out a lot more to me as an experience that remains remarkably fresh, with a unique and powerful thematic focus that feels even more prescient today, and a play style that seems altogether appropriate to it. I've straight-up fallen in love with this twisted version of Hyrule that is Termina! I think I now like it even better than Ocarina of Time. It's aged better and gets to me more. Just goes to show that sometimes trying something very different is just the right course after all.

Correct you are. Playing as Luigi was definitely more fun in this game for me.

Remaining clues (added some more)

#36 (incorrect guesses - A Short Hike)
- Do you want to go hiking or mountain climbing?
- I killed him earlier, why’s he still on the floor? Oh well, I’ll walk past and… no, wait, he’s alive, and more deadly than before.
- Opening that door is a riskier move this time around.
- There's a moment late on where running is a risky move. You're in trouble if you haven't cleared the hallways beforehand.
- A lot of iconic dialogue is now sadly missing.
- Remake of a game that itself was originally intended to be a remake.

#30
- Now you have to collect stat points and equipment upgrades, rather than finding / earning the money to do so.
- Features the first appearance in the series of a person better known for featuring on a stunt / prank show.
- There's also a Marvel character and a Star Wars character available as unlockables.
- Like other games in this series, it features a soundtrack of licenced songs from rock and hip hop artists
- The game's title features the name of probably the most prominent figure from this particular field.

#26
- There’s more toilets this time round.
- And a lot less variation when playing from the alternative perspective.
- The stalker is now more attentive and persistent...
- ...although he loses the element of surprise by making so much damn noise.

#24
- Many who have played this will surely have experienced heartbreak in the engine room.
- One of the heroes here first featured in another game in a different genre. The other makes their gaming debut here.
- Our heroes show they can play their namesake instruments

#23
- You can trust those little simians in the opening level, but after that they’re going to start attacking you.
- You visit five different locations in this game. The first and last are preset - you get to choose which order you visit the middle three in.
- The console version was less forgiving due to a different save system, and being unable to adjust the brightness of the visuals.

#22
- Wow, those birds are well armed and have serious bank.

#21
- Not sure how all those birds have survived so long, seeing as water damages them.

My list so far

Adding the 3rd hint for these remaining games:

24) To be fair the game does warn you when you go down the dark path
Hint 2: Which is appropriate since it's a lot harder
Hint 3: Though I didn't really have a bad time until maybe the fiftieth time dying to the final boss

23) While this game is quite literally unfinished, I still think it's worthy of this spot
Hint 2: That's gonna have to wait. How long? Maybe a day... maybe another 2 years.
Hint 3: The name of the game is an anagram for it's more famous predecessor.

21) Is it just me or is the villain of the previous game staring at you the whole time?
Hint 2: There's certainly something rather ominous up there
Hint 3: And you only have 3 days before it comes crashing down

Majora's Mask

That was quick :D

Right of course.

Hmm, Deltarune?