StarCorridor
You will not find a more 2000s game than this. Simple Plan and Smash Mouth on the soundtrack. A partnership with Nokia cell phones. Some of the most butt ugly fucking character designs ever in the Olliewood stage. Incredibly, incredibly aged but that's half the fun. There were a lot of bad Pro Skater knockoffs in the early 2000s - this wasn't one of them.
2013
This game has one of the most stellar stories you'll find in gaming, with great character-based storytelling and chemistry between the two main characters. The gameplay leaves something to be desired, there's times where it gets a little slow paced and even the most suspenseful of moments struggle with awkward gameplay mechanics. The story ultimately overshadows it, though, and this is worth playing just for how engaged you'll be with the characters alone.
2019
2005
I'm not even kidding when I say that from ages 6 to 10, Club Penguin was a fucking lifestyle. I took days off school to level up on Card Jitsu, we had class-wide discussions on the debut of the fucking orange puffle. I went on those stupid tracker sites to see when Billy Bob of the Penguin Band was online. In one of my most most evil childhood moments, I stole the code off a puffle plushie my friend got for his birthday to use on my account, because I guess cart surfing for those same coins just didn't cut it. I didn't fuck around with my love for Club Penguin, and may it rest in peace.
2003
1998
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2008
No joke - I got this game in 2009 for successfully getting through surgery as a kid. I was rewarded with a game so memorably bizarre that it's become a meme since. This game literally has a LAUGH TRACK in it and is about collecting bobbleheads and mind control. You throw pastries at enemies. There is a remote-controlled fly that you guide through air vents. Cory in the House is truly an experience, and I'm not even joking. Play this. You'll never forget it.