Jerry Seinfeld, Lewis Black, Joan Rivers and the entire Boston comedy scene from the 1980s. While the trend is fairly new, 95 Miles to Go isn't on the bandwagon. In fact, it's actually quite a few years old, and it was made not long after Comedian. It follows Ray Romano and his longtime opener and friend, Tom Caltabiano, on a short tour through the South on a break between seasons of Everybody Loves Raymond, where Caltabiano was also a writer. After a run on HBO and a short break, the doc is finally available on DVD with a ton of extras.
The movie is simple. Ray Romano does not like to fly, so he and Caltabiano took a flight from Los Angeles to the first stop on their small tour, and they drove the rest of the way. Romano didn't want to film the trip, but Caltabiano gave him no choice. He brought an intern from Raymond, and they duct taped two cameras to the dashboard of the rental car. It was really basic, but it worked. Plenty of footage was caught throughout the trip, including a series of Romano's "mind bets." Mind bets are little gambles he takes with consequences if he loses. For example, he has to perform a task so many times in a row or he can't golf for a week. We see him lose some of his mind bets during the movie. His psychosis is really interesting, and it gets a little weird.
The extras are really great. They include two Q&A sessions from screenings promoting the DVD release. They also include a commentary track with Ray and Tom, two more commentaries, a photo gallery, deleted and extended scenes and best of all, a full stand-up show. It was truthfully the first time I've seen much of Romano's stand-up act.
While the documentary is not heavily planned out or produced, it really gives a nice honest insight into what comedians do when they're on the road. The interaction between longtime friends is always amusing, and it was a good watch. The extras are enough to make the DVD worthwhile, and I think it's definitely something any comedy geek should see.