This fly on the wall experience follows Ray Romano and his friend and opening act Tom Caltabiano as they engage on an 8-day 7-city stand-up tour while driving from Miami to Atlanta. This candid experience is filmed not with a giant production crew but with one intern Roger Lay Jr. who is just as much a character in this documentary that follows the highs and lows of touring. What could easily have been a forgettable snooze-fest instead turns out to be an eye-opening glimpse into the life of TV star Ray Romano that has more than its fair share of laughs and enjoyable moments of awkwardness.
The film kicks off with Ray heading to the airport, and it’s along the way there he reveals his fear of flying which explains why once touching down in Florida they will be travelling by car through the duration of the tour. It’s inside the car where a good portion of the documentary takes place and where from duct-taped dash cameras we watch Ray and Tom banter through such topics as Tom’s chronic tardiness, Ray’s insecurities with fame, how the production will come together as well as Ray’s “mind bets”. The “mind bets” are best explained by Ray when watching the documentary, and it’s one of those little things that allows the viewer to not just see him as more than the character from his sitcom, but as a regular guy with a few quirks.
There is more to this than just two guys in a car; with every city they stop through we get to see snippets of the stand-up act by both Tom and Ray. These moments are often hilarious and even become part of the behind-the-scenes narrative after Ray tells a raunchy joke at a corporate venue. Getting to see behind the curtain what happens when an off-color joke is made is something most viewers or audience members would never even think about, but we get to see Ray’s concern with the consequences that could have been. The time spent here shows it’s not just about showing up and doing the act, but there are pictures to be taken, hands to shake, and autographs to sign. Though he seems to have trouble believing his fans genuinely like him, it’s endearing to see how he treats fans throughout the documentary who approach him. In particular there is a humorous moment when a fan approaches him inside a Chinese restaurant that has one of the best payoffs of the documentary.
Granted you would think these guys would be out on the town and partying after their shows and engaging in activities with the groupies that may cross their path. Instead we get them hanging out in their hotel rooms. Watching Ray and Tom bicker with one another and have deep conversations over bagged nuts may sound dull but actually is pretty entertaining.
To even give a favorite moment in this documentary is so difficult because I really enjoyed this 79-minute glimpse into life on the road…but I’ll say the scenes involving the tinted windows and later on when Ray discovers his water bottle has been opened are pretty priceless in my humble opinion.
What first-time director Tom Caltabiano pulled off here is something fresh and entertaining, and hopefully we’ll see more in the coming years from him. The decisions to go low-tech and with the fly-on-the-wall approach simply were the perfect choices in allowing us to feel like we got to really know these guys by the time the credits played. The other unsung hero here is the camera guy Roger; how he managed to capture some of the more emotional and revealing moments made this more than a simple behind-the-scenes or home video experience.
The DVD doesn’t just offer us this insightful and entertaining documentary. This thing is filled with commentaries and extras that kept me busy for hours. The video commentary with Ray and Tom is just as good and revealing as the documentary itself and shows the great chemistry that these two have developed over the years. The decision to go with the video-in-picture commentary was a great one; it’s fun to see these guys react to themselves and each other as they tell us more stories that went on that we never got to see. Another of the commentaries has the camera operator and the editor, which is a good track to listen to for any budding filmmakers out there and also shows a glimpse of what went on behind the camera and the edit suite to make this come together. Still there is so much more on this DVD with a 30-minute special of Ray Romano’s stand-up act and Q&A’s from the screenings of 95 Miles To Go and several deleted and extended scenes. This is a great DVD that’s been put together with care and will satisfy all long time Romano fans and those recently discovering him.
Check out Gino’s interview with the director Tom Caltabiano for a more in-depth look into the production and the post-production of the documentary.