Is this a Total War game? Rome or Shogun.

I guess this will need another hint, it is one of my more obscure games:

21) Ends with falling (depending on the ending)

The titular character is the protagonist's darker alter ego

Earthbound meets horror

The titular character is always in black and white, including on the cover art

Yes! It is Rome.

The main game is about the Roman Republican era, while the first expansion is set towards the end of the Imperial era in the western half. The second expansion however doesn’t feature Rome at all, since it’s about the rise of Hellenistic Greece a little under a century before the start of the main game.

As a quick overview for the guessing game - Darashiva now leads with 8 guessed games before Machina with 7. The rest is quite a bit behind, lead by S.Peelman with 3 guesses. See here.

Let's add some hints for the unguessed games:

#25: The Secret of Monkey Island as guessed by Darashiva.

#24: Graveyard Keeper as guessed by Darashiva.

#23: Day of the Tentacle as guessed by Underwater Funktown.
Bernard, Laverne and Hoagie on a time travel adventure.
The time travel device is called the Chron-o-John, because...

#22: Return to Zork as guessed by Underwater Funktown.
Return to being eaten by a Grue.
This is part of one of the oldest game series, but this entry is with graphic instead text only.

#21:
You mess up so bad, your kids need to time travel and help you.
Part of an old series, this game was a turn-around point with it's success.

#20: Baldur's Gate as guessed by Darashiva.

#19:
The game has some innovative ideas, mainly it tries it's hand at procedural story generation and character growth, meaning each playthrough is different.

23) Day of the Tentacle?

22) Return to Zork

Correct on both.

29
- This ‘trophy’ of sorts you get by defeating a powerful enemy was once required to progress through the game, but now it’s just a means to make some money.
- And you used to be able to avoid these deadly sisters, but now you have to face them.

27
- Whilst conservation of ammo was a feature of the first game in the series, in this sequel you’ll have a supply that is pretty much limitless.
- Seeing as this game is a lot more action-orientated and combat heavy than its predecessor, the abundance of ammo makes sense.

26
- Find every main collectable in the game and you’ll then get the opportunity to double your haul, as more of the same collectable appear (although different coloured), hidden in the levels you’d previously played.

25 - Super Mario Odyssey
- That piece of clothing has never been more important to this character than it has in this particular game.

24
- Avoid picking up items early on, and you may come across an additional enemy that will reward you upon defeat

23
- In reference to game 24’s first clue - in this game you’ll find out how this enemy came to be.

22
- As you play through the game, it helps to pay attention to what you’ve seen, what you’ve heard, and what you’ve been told, as that knowledge will come in handy later.

Current list - https://gamrconnect.vgchartz.com/thread/247804/the-official-thread-the-14th-annual-greatest-games-event-post-only-once/4/#3

Let's get the next set of hints going so I don't fall behind.

#20

-Glory to Mankind

#19

-The main protagonist is essentially an unreliable narrator, thought it's not really his fault

#18

-Humanity was wiped out around a thousand years ago

#17

-Warring Triad

#16

-An option for the main character to engage in a romantic relationship in this game's DLC made some silly people very angry

19) FF7?

18) Nier: Automata?

17) FF6?

19 and 17 are correct, 18 is not.