If a road trip wasn't a good idea, they wouldn't have wasted DJ Qualls' time making a movie about one. Confirming that notion, Rental Car Rally
Speeding in blindly behind their successful 36-hour rally from NY to Montreal, RCR is a competitive backroads-mostly road trip in rented whips (though you can use whatever) motoring from the Chi to Toronto, the most ballerific metropolis in all of Southern Ontario (eat it, Oshawa!).
As in races past, teams of two or more (who're passive aggressively encouraged to ornament themselves via costume) will taxi their rides to a super-secret Chicago start point at midnight, snag a provisions briefcase filled w/ energy drinks, cigarettes, chaw, and beef jerky, then burn north along five checkpoints -- sort of like a neo-underground railroad, except instead of freedom, it's for the sweet energy drinks, cigarettes, chaw, and beef jerky.
The race is scored on a 100 pt scale broken down into three categories: lowest mileage reading from start to finish (50 pts); "Team Style" judged on awesomeness of costume and closest "metaphorical consistency between the costume and the team's rally vehicle" (40 pts, past winners include four dudes dressed as a wedding party); and 10 points for "Freelance", which includes "spectacular feats of daring-do" like doing a sick jump over a canyon or climbing in the backseat and putting your complete trust in the rhythm method.
At the after party, the "Style Winnah" and overall "Winnah & Champeen" can proudly hoist their now-legendary golden gas pump trophies, while the overall winner also gets the chance to swim Scrooge McDuck style through $2K in prize money, the very same sweet fee Qualls pulled in for The New Guy.