You went for a second play through? That is the best compliment one can get in a jam :)
The dialogs (and the progress overall) is triggered by the amount of crashes you have. So it makes a difference how many objects you hit. But the dialogs themselves stay the same. Different dialogs based on the "score" of the player sounds like a really good idea, we never even thought about it. Random ranting of the other drivers would have been an option, but got cancelled because of the lack of time. I will put your idea on our Trello board for after jam reworking. That would enhance the replayabilty of the game a lot :)