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Jumpin said:

To kick things off:

Cruis'n USA. A fairly obscure racing game on the N64 that I picked up dirt cheap in a bargain bin long after the N64 had ceased to be relevant. To be honest, I got it as a joke.
Indeed the game is every bit as terrible as it sounds:

1. According to the game, about half of the parts in the US that are notable to visit are in California, as that's where the first half of the game is located. Once you leave California, they start reusing music, and many of the levels look the same as others.
2. The Red Wood forest level is one of the lowest framerates you'll ever experience on the N64.
3. You can apparently run down red-woods with ease, but palm-trees are invincible.
4. Cars always land on their feet.
5. Every race ends with this really awkwardly writhing woman with a trophy. I think she's on drugs.
6. All races are easy, within 4 seconds, you leave the competition in the dust, and not see them for the remainder of the race.
7. The soundtrack is seriously one of the awesomest and most disgustingly cheesy of all time.
8. Parties always occur on the roof of the white house, even when they include cattle.

This game puts a smile on my face to play.
It currently holds a score of 50.63% on Gamerankings

Behold! Cruis'n USA in all its glory... yeah-hah, whoahoahoah!

Fun Fact #1, the woman with the trophy at the end of the races was a real porn star (I forgot her name tho)

Fun fact #2, in the arcade version of the game the woman was in a bikini top instead of regular clothes in the N64 version

N64

Arcade