95 Miles to Go Movie Review

Despite what TBS and CBS would have you believe, everyone does not love Raymond. In fact, there are moments where his perturbed and annoyingly nervous comic style feels like second-hand Woody Allen without the wit. In fact, the only reason I ever get around to watching the show is because of Peter Boyle. For all intents and purposes, I’m no Romano fan. So, maybe that’s why I so begrudgingly gave into the documentary 95 Miles to Go and its strange dichotomy.

On a tour of the Southern states, Ray Romano, as always, took along longtime friend Tom Caltabiano to be his opening act and professional shit-taker. What Ray doesn’t know is that Caltabiano dragged along an intern from Everybody Loves Raymond to film the entire drive through the last eight days of the tour. What comes out is the neurosis of a popular comedian, the stresses of touring, and the fragility of a friendship that is mixed with business. However, it’s all put on a leash.

Where Christian Charles’ fascinating Comedian opted to show the dichotomy of fame and the early stages of struggle to get into the business, 95 Miles to Go is breezier and keeps its eye on Romano’s uncontrollable neurosis and using Caltabiano not so much as a rising star but as a source of logic. It’s an interesting idea, and the film on the whole works, but the movie is blunt and never really dives headlong into that neurosis (partly because Romano was allowed to approve the last edit). Caltabiano knows Romano’s ways from way-back-when, so he rolls his eyes both at the old school-chum he knew and the behemoth of nervous, sometimes excruciatingly frustrating obsessive behavior.

What is so strange is that we are both impressed and annoyed with Romano’s ways. The worrying about the “gay” shirt is aggravating, but the self bets are hysterical. I found Romano’s worrying about money grating, but the Aquafina scene had me rolling in the aisle. For every time I laughed, someone else was rolling their heads in exasperation. If this had been plumbed even deeper, 95 Miles to Go could have been an absolute stunner of fame-induced paranoia, but it’s happy where it is. Since the movie generates a solid amount of laughs, especially in the clips of stand-up, I can’t say that I disagree with the tactics, but I can’t help but think of the potential the film had.

However, in the end, this is just a decent piece of entertainment to pass the time, and it fulfills its duties as such. Romano’s stand-up has many more potent laughs than his show; much like Tim Allen’s fantastic stand-up is ten times any episode of Home Improvement. As Romano and Caltabiano sit in a Cracker Barrel in Macon, Georgia (shockingly, I’ve been to that very Cracker Barrel), we see the struggle of friendship and business as Romano worries over what the edit of the film will paint him as. In a moment like this, of pure self-consciousness, we see the struggle between a comedian’s humor and self-esteem. We just need more of these momets.