Well well. All three are correct!

I should've added #21 as well.

Loud hint warning.

Was gonna guess Ocarina, but I see you already have that up at 26.  

Majora's Mask?

That's it. Is this song in Ocarina?

I enjoy seeing entries like this in people's highlights; getting the chance to learn about quirky titles like this that I hadn't noticed before but might just enjoy.

(Wanted to say that I'm dying to try this game, but couldn't find a good contextual excuse. Sorry about that letdown. It was a grave omission, I know.)

It's sounds reminiscent of one, but I also haven't played Ocarina in a long time.

Maybe, but I think it's from Majora's Mask only. I mean, I picked it because there's lots of similar sounding songs in N64 games, but I guess it was pretty easy to guess anyway.

New hint time:

25) Ace, Snake, Santa, Clover

24) To be fair the game does warn you when you go down the dark path

23) While this game is quite literally unfinished, I still think it's worthy of this spot

22) The Little Prince

21) Is it just me or is the villain of the previous game staring at you the whole time?

#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.

#34
- The guy who dies shortly after you arrive on location shares his name with a guy who suffers a similar fate in a movie franchise that no doubt influenced this game.
- Whether you get more puzzles or more combat depends on which team mate you choose to follow at certain points.
- Made in the same mould as another, more popular series from the same developer. Although this game utilises 3D environments, which the other series hadn't done at this point in time.
- Was followed by a well received sequel. However, the third mainline entry killed the series stone dead.

#33
- Smelling of urine isn’t necessarily a bad thing.
- And looking at the guard’s butts can be advantageous at one point too.
- You could run into issues early on if you haven't got the case.
- A lot of names have animal references.

#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.

#29 - Correctly guessed - Grand Theft Auto
- Features a soundtrack of original songs from fictional bands, that was also available on a separate CD.
- This game, its expansion, and its first numbered sequel are currently unavailable to buy. Bit of surprise given the popularity of the franchise. Surely not the developer looking down on them?
- Was quite a controversial game at the time of its release.

#28
- This game was named differently depending on the region of release. The recent re-release combined these two names in a way that is pretty clever when you think about it
- One of the original titles shares its name with an iconic heavy metal album. The theme of this game is also the same as the album cover. Surely not a coincidence.
- It was released on two home consoles, which had some minor differences, including in level design. The recent re-release worked to merge these two level designs. There was also a PC version with the same name, but this had completely different levels.

#27
- After seeing what the ghost in the party hat did to his flatter self, perhaps our hero wanted a piece of that action 13 years later.
- Previous games of this style in this series usually had a set number of the main collectible to find. This game greatly exceeds that.

#26
- There’s more toilets this time round.
- And a lot less variation when playing from the alternative perspective.

#25
- Revisiting the levels post game with another character is more unique this time round.
- For the first time in this particular style of game in this series, the hub world is greatly reduced. Level selection is done using a basic map screen.

#24
- Many who have played this will surely have experienced heartbreak in the engine room.

My list so far

I'm really drawing a black mostly here, but this maybe;

The original Grand Theft Auto?