Watching Ray Romano Come to Terms With His Fame on the Road in ‘95 Miles to Go’

It’s no secret that sometimes comedy is taken a bit too seriously. Comedy obsessives love not just the jokes, but the mechanics and emotions of the comedy world. There are a raft of comedy documentaries exploring comedy and comedians, but do they really have anything significant to add to the discussion? This series looks at comedy documentaries and whether they’re interesting, insightful, and possibly even…funny?

95 Miles to Go, as the title suggests, is a classic road movie. In the summer of 2001, following the fifth season of Everybody Loves Raymond, Ray Romano and Raymond writer Tom Caltabiano hit the road for a very unglamorous stand-up tour of the south. “Against Ray’s wishes,” the film informs us, “Tom filmed it all.”

In this type of film, the need to document the trip chronologically can lead to long periods of relatively little action, so themes tend to develop slowly over the course of the movie. Here, the most interesting element is watching Romano in the process of accepting his recently acquired super-stardom. He’s cautious enough to check into his hotel under a pseudonym, but his lifestyle isn’t yet extravagant penthouses and private planes. It’s average hotels, rental cars, and a lot of Subway sandwiches.

He’s swamped for autographs and photos everywhere he goes, but he’s detached from the praise. “The weird thing is, you know all this adulation?” he says after meeting a crowd of fans. “There’s a part of me inside that thinks — that doesn’t buy it at all. Like, there’s something in me that thinks, any split second they could turn on me and say, ‘oh you’re really a dick and we don’t like you.’”

In some ways, it’s an old Hollywood cliché of stardom. But it’s nevertheless interesting to watch someone working through it in real time. Though his trademark schlubby charm is clearly genuine, his act is just that, and he’s still dealing with being a real person only known for a particular side of personality.

Inevitably, his material also evolves. Early on, a joke about being the “noise checker-outer” in his house was distractingly familiar to me; I realized that it was in the set Romano had done as a young comic on Carson’s Tonight Show. Later, a story about contemplating ordering porn in a hotel room begins with, “That’s not me, you know that. That’s not Everybody Loves Raymond.”

There’s even a fleeting conversation about his now-enviable financial situation, longing for the good old days of bringing home a check in hand, rather than abstract figures being funneled into his “machine”.

The money thing also becomes an issue in the other ongoing theme of the film, the increasingly strained relationship between Romano and Caltabiano. At one point, while Romano is out playing golf, his opener has charged $75 worth of room service to his tab. The usual issues that arise between any pair spending far too much time together are multiplied when one party is a rich, famous television star.

To Caltabiano’s credit as a director, he leaves in a lot of Romano’s criticism of him, making Romano out to be the hero of the piece. They even have a fight about the editing of the documentary, followed by a cute bit over the closing credits showing Romano’s complete lack of understanding of how a multi-camera documentary comes together.

The real value of 95 Miles to Go comes from its unique timing. A few years earlier, Romano and Caltabiano would have just been two guys on the road; a few years later, Romano will be an Emmy-winning actor with one of the most successful sitcoms of all time under his belt. But for the moment, he’s still figuring it all out.

And so, in conclusion…

Is it interesting? Not wholly. Some of it, especially towards the beginning, feels a bit like being on a long car journey. There are intriguing moments sprinkled in, but it’s not engaging from start to finish.

What does it have to say about comedy? Watching Romano riff material on the road is really fun. As in Jerry Seinfeld’s new web series, it’s fun to see how much of these famous comedians’ stage personas are rooted in the way their brains actually work.

Is it funny? Sometimes. The funniest bit comes from our two leading men doing a Q&A after a show. They both come across as sharp, hilarious, and completely charming.

Can I stream it on Netflix? Yup!

Any comedy documentaries you’d like to see discussed? Do let me know.

Elise Czajkowski is a freelance journalist in New York City. No autographs or pictures, please.

Watching Ray Romano Come to Terms With His Fame on the […]