This is Route 66: The Marathon Tour. It's a boxed set of 5 DVD's that cover the route from Chicago to LA, in a lighthearted way. The series includes segments about famous sites on the way, interviews with owners of landmarks and historians, and is just generally fun to watch.
The reason I think this set is a good planning tool, especially for the first time Route 66 traveler, is because you get to see the route in motion. Not only that but the series helps capture the spirit of Route 66 as the interviews give you insight into life along the route, and what it's like to explore it. It may not be a bad idea to watch the series with a notebook in hand, or a tablet computer so you can look deeper into some of the sights mentioned.
The only problem I have with this set is that it is a bit cheesy at times. That and most of the funding to put the series together came from Hampton Inn's and Cheverolet so at times it does feel like a bit of a commercial.
Overall though, this is a great "Winter Watch". It's a excellent tool for planning, and just getting you tuned into and ready to travel the Route.
If you interested you can find this set on Amazon, in the green collectors tin for $10 or less.