Just what the title implies. I'll try to write a short note about each game when I can to keep this from getting boring.
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Ellen McLain's brilliant deadpan snarking as GLaDOS and the power of SCIENCE! turn what could have been a really dry puzzler into a short, but memorable experience. Nothing is more satisfying than finally being able to finally figure out a Portal puzzle that you've been stuck on for hours, though. The payoff is the most satisfying thing ever.
Brilliant puzzles that keep death from getting too annoying, brilliant voice acting, brilliant, consistently funny script, stellar soundtrack, awesome graphics, co-op missions...you can't go wrong with Portal 2.
Don't focus on the hats. Focus on the fact that the characters are funny, lovable, and unique, the art style is beautiful in a very subtle way (I wish there was an artbook for it), the fact that you can customize the way you play as little or as much as you want...it's great for something that started out life as a mod. And now it's free!
One of the funniest, most quotable games I've ever played (it's up there with Portal and Portal 2), and totally worth getting even if you're like me and you're not exactly an ace poker player. If Telltale never makes a sequel, they'd be missing out on a huge opportunity.
A better poker game than the first, with just as solid humor, and even more...story, believe it or not. Love the custom Inventory tourneys and "story arcs" the characters will update you with every so often. And how can you say no to a game where Brock Motherfuckin' Samson & GLaDOS get to interact?
I love any universe cartoony enough to just accept a giant sentient space-gorilla has been defeated by a talking dog who wears pants (and carries a gun) and a hyperkinetic talking rabbity thing with psychic powers. Once again, Telltale writes some of the funniest games in existence, other than Valve. The difference is, Telltale actually releases their episodic gaming content ON TIME.