Dean and Sal drive a Cadillac across country to Chicago. Or rather, they start with a Cadillac, and they end up with a big hunk of destroyed metal. What destroys this car, you ask? Primarily, it’s Dean – Dean’s mad, fast driving, his need to move, and his dangerous lifestyle. Now for the symbolism. The Cadillac is an American car, and a big beautiful Cadillac is all tied up with the Big Beautiful American Dream. The Beat Generation is running around rebelling against the American Dream, and destroying in it their trips across country with their mad, fast driving, their need to move, and their dangerous lifestyles. Ohhhh.