OK, after the first hint I thought already Simcity but was too unsure. But Simcity 2000 was a thing and matches your second hint, so this must be Simcity 4.

#42
- mZuzek can't stop talking about how much he loves this game
- 4 (+1) islands
- Get in the bag
- Players can participate in Global Missions
- Hawaii
- You can't go to the gym anymore in this game

#36
- Fighting game based on a cartoon
- This N64 game got ported to PC two years later
- Simon & Garfunkel originally named themselves after this duo
- The playable characters are 2 cats, 2 mice, 2 dogs and a duck

#31
- Plants
- Plant them on the right square

#30
- 8 games
- This character stars in a new game coming out very soon

#29
- The second game in the franchise. It's the best selling one, not counting spin-offs.
- A famous flying sidekick gets introduced in this game

#28
- Shows off the capabilities of the system, you don't even need to use buttons!

#27
- Remake of a game released in 2000

#42: Pokemon Sun/Moon?

#36: Tom&Jerry maybe?

#31: Plants vs. Zombies?

#30: Metal Gear Solid?

#29: Sonic 2?

#28: Wii Sports?

#42 Correct!!! Finally someone got it

#36 Right franchise... Now the game! (Although I'm not sure if anyone here could guess it, it's rather obscure.)

#31 Correct!

#30 Nope.

#29 Correct!

#28 Nope.

#27
The Legend of Heroes: Trails of Cold Steel
(Change YoY: Same position)

The Legend of Heroes as a series is one of the biggest positive surprises I've had in the last decade. Trails of Cold Steel was the third game in the franchise that I played and it's just as great as the first two games that made me a fan of the series. One of the reasons why I was so surprised about these games, is because how well they are written. The story and characters are some of the best I've seen in video games, and no matter how many different characters these games feature, each always has their own unique personality that stands out from the other characters. 

Adding to this is the excellent gameplay and battle system that I never got even a little bit tired of. These are genuinely among my favourite games in my absolute favourite video game genre, and as a series the only one in the genre that I still rank higher is Final Fantasy. At this point, I'm simply waiting for the third and fourth games to be localized so I can get back to these games and finish the story.

Heh, it’s funny that you mentioned the two games on either side of the one I meant.

3000 was the first one where putting two roads right next to each other didn’t result in a chain of crossroads, but rather a nice lane with trees. 4 took this much further by introducing many types of different roads. However, guessing 4 will be correct at some point.

22: One of the newer Ninja Gaiden games had you fight against the Statue of Liberty. I'm gonna say it was Sigma 2.

Oh, and the hint on 24 made me chuckle a bit since I immediately thought of at least a dozen different games from the 90s this could apply to.

25: The Wind Waker

24: Resident Evil?

Really? I don’t just want to look, and my memory isn’t good enough to remember what you had on 23 last year. And every year. Must be something I talk too much about. Or something we talked about recently. I talk too much about Zelda and we recently talked about how I should really get Okami...

Is it Ocarina of Time?

SimCity 3000

• Windows PC
• 1999
• Construction & Management Simulation
• Maxis/EA

'SimCity 3000' is one of the most famous games in the 'construction and management-simulation' genre, for short; the city-builder. And that's what it is, the player builds the best city they can possibly make, trying to earn as much money as possible and have it be a home to as many people as possible.

The game takes the gameplay of it's groundbreaking predecessors and fine-tuned it further to give a more realistic gameplay experience. There are many more things to build and zones will grow in a way more realistic than ever before and now, neighboring cities come into the mix although their influence remains minor.

I had played 'SimCity 2000' fairly regularly already, and the new game quickly grabbed my interest. It wasn't however, until I saw one of my aunt's cities that boasted many skyscrapers and luxury apartment buildings that my interest really peaked. I started creating city after city and each one got better but my magnum opus city still only got to around 350k inhabitants, using just half the map. The interest then moved on to another game years later, but definitely remained in the genre.