95 Miles to Go (2004)
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Ray Romano's observational stand-up is solid. The snippets of it is pretty good. The problem is the road trip. It's bland. The problem is that he's not performing. It's simply the guys being bros without any drama. Their friendship comes through as almost a married couple. They're comfortable with each other and it shows. Sadly, it's not exciting and there is not much comedy in that. His little observations and neuroses are interesting but not actual laughs. Much of it is home video quality with the sound to match. One does get a sense of their friendship and that's something great for fans.
I have nothing nice to say about this film. Ray Romano has never been a great comedian, and even his sitcom was successful because of Peter Boyle and Brad Garrett. Here, we see just how awful and unfunny he can be.
The clips from the stage are not funny, with his observations on life not being clever, original or quirky. He has nothing to offer his audience, and only a small group seems to enjoy his style (elderly women). The stuff from his hotel and more is even worse... wow, such a boring man. If you want to be a professional comedian, watching this film can teach you everything on how to not be successful.
When you think of a comedian tour film, you think of comedians joking with each other, riffing, playing practical jokes, and taking turns insulting each other. In short, being funny. But there's very little of that in this film. Far too much time is spent demonstrating that being on the road is boring for the most part. The concert footage is funny, but it's almost entirely old material which Romano and Caltabiano have since performed on TV.
One redeeming element is the interesting contrast between the Ray Romano who takes the time to shake hands and sign autographs even when he's running late, versus the insecure, whiny, complaining Ray Romano.
95 Miles to Go will be of interest only to viewers who are fascinated by the life of the stand-up comic on the road. If you're expecting hilarity, you'll be disappointed.