I think the strangest game I've ever played was Chulip. Basically, the game is about you, the new kid in town. Before moving to your new home, you have a dream where you kiss a girl under a tree. When you arrive, you see the girl of your dreams but she wants nothing to do with you. So what is your solution to wooing her? Kiss everybody in town and I MEAN everybody, including males, females, and various non-human entities. It's a silly little game that is often funny and always weird. I actually really like it and you can get it for $3 used on the PS2 at Gamestop. Fittingly, it came out on a Valentine's Day. I found the game online and thought the concept was interesting so I went to buy it. When I did, the game store employees said they had literally JUST been talking about how no one was ever going to buy that game. Lol.
The second weirdest game I've played is probably Dog's Life. You play as, you guessed it, a dog whose love interest has been captured by dog-nappers. It's your goal to find her and save her from this evil group of people. Along the way, you'll do a lot of sniffing and periodically have control over other breeds of dog. You'll have to eat food to stay healthy and what goes in must come out (and by that, I mean you are literally required to poop which you can then pick up and throw at people if you so desire). You can pee, perform tricks, herd sheep, scare mailmen, and a number of other things that doggies tend to do, all provided with witty commentary by you (Jake the dog) and other dogs and people. It's a cute game and if you don't mind potty humor, it's great for kids. I don't have it anymore but I'm actually considering getting it again because it's just so silly and fun (though sometimes repetitive as kid-games are). You can get it for $10 used on the PS2 at Gamestop.
The second weirdest game I've played is probably Dog's Life. You play as, you guessed it, a dog whose love interest has been captured by dog-nappers. It's your goal to find her and save her from this evil group of people. Along the way, you'll do a lot of sniffing and periodically have control over other breeds of dog. You'll have to eat food to stay healthy and what goes in must come out (and by that, I mean you are literally required to poop which you can then pick up and throw at people if you so desire). You can pee, perform tricks, herd sheep, scare mailmen, and a number of other things that doggies tend to do, all provided with witty commentary by you (Jake the dog) and other dogs and people. It's a cute game and if you don't mind potty humor, it's great for kids. I don't have it anymore but I'm actually considering getting it again because it's just so silly and fun (though sometimes repetitive as kid-games are). You can get it for $10 used on the PS2 at Gamestop.