Richard Hayden strikes us as a smart guy, while not keeping an eye on ‘Ol Tommy Boy out there – he can be found with his fellow nerds in the nerdery crunching numbers. Early on in the sales trip, the boys find themselves filling up in the Illinois countryside making their way to Davenport, IA… 22 miles away.

We have always wondered, 1, how Richard did not know he needed a new map and 2, where the hell were they? Now, with roughly 63,535 minutes of our lives accounted for in watching Tommy Boy – we felt it was time to do some digging.

Prior to the stop near Davenport, Richard and Tommy had departed Sandusky, Ohio we are assuming west on I-90. After taking no for an answer on multiple occasions, they are asked to leave during Tommy’s ambulance show in the office of a customer. Based on the suit, the larger office and the collection of classic cars, we put this guy closer to the Chicago area than deep in Indiana.

From there, they would have headed down I-88 out of northern Illinois, on their way to Iowa. That long stretch from the Chicago suburbs down I-88 had them stop for gas and directions, 22 miles from Davenport, IA – in the small Illinois town of…

Hillsdale, Illinois

22 Milezzzzz away from Davenport across the Memorial Bridge over the Mississippi River, sits Hillsdale, Illinois. A sleepy town off the highway, a great stop for food, gas and taking in Main Street for all its charm and sarcasm. These traits match closely to the backdrop of the scene. So there you have it folks, mystery solved.

… But the scene itself, well,  more than likely shot somewhere in Ontario, Canada – where a majority of the movie was filmed. But it will always be Hillsdale in our hearts.

Cheers…