Going on the Road with Doug Benson in ‘The Greatest Movie Ever Rolled’

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?

“I’m making a movie to raise money to make a movie about going on tour to raise money to make a movie about the tour,” Doug Benson says on stage at beginning of his new documentary, The Greatest Movie Ever Rolled. He then admits that the clip of him saying that will probably be the first scene in the movie. “My life is so easy, you guys.”

And actually, that appears to be true. Unlike his previous effort, 2007’s Super High Me, which had a built-in structure thanks to its inspiration (Morgan Spurlock’s Super Size Me), The Greatest Movie Ever Rolled is essentially a tour documentary glossed up as an experiment in comedy and weed, this one inspired by Spurlock’s more recent The Greatest Movie Ever Sold.

As a tour diary, the movie is likeable, fun, and funny, but there is really no drama and no story to speak of. The biggest issues are that sometimes Benson has to get up early to do useless local press, and occasionally drunk moms in miniskirts won’t stop hitting on him. Co-starring his non-pot smoking opener and friend Graham Elwood, the film will feel almost eerily familiar to anyone who listens to the rental car episodes of Doug Loves Movies, which often feature the two of them playing movies games and making fun of each other. Fans of those episodes will love the movie, as the two make a great team, and they seem to be having fun together both on and off stage.

But for someone with four stand-up albums, three regular podcasts, and now two documentaries, Benson reveals surprisingly little about his personal life, or his thoughts on much other than marijuana and movies. At some point, it feels hard to justify spending this much time with a comedian who isn’t willing to share more. At one point in the film, while wandering around Chicago with an incredibly high Benson, Elwood can be seen starting to lose patience with his stoner friend. But whether there was actual tension there, we’ll never know; neither seem like the type to have a big fight, certainly not on camera, so it just passes.

Early on, Benson says the point of the movie is to show people what life on the road is like for him, and a lot of people will love it for being just that. Even as someone who doesn’t smoke pot, I thought it looked like fun. But then again, I always assumed going on tour with Doug Benson would be fun; I was hoping for a little more from this.

And so, in conclusion…

Is it interesting? Well, yes. Much like The Comedians of Comedy, there’s no real journey, but it’s a very enjoyable 80 minutes.

What does it have to say about comedy? As much as anyone in this world of niche comedy, Benson has found his scene — movie-loving stoners who make elaborate name-tags so they can play an intricate film trivia game at a comedy club. That he’s able to make enough money playing to those people to make a movie about the tour is a testament to how well he’s branded himself.

Is it funny? Yes, absolutely. For one thing, in another time and place, Benson and Elwood would have been a fantastic vaudeville duo. The combination of Benson’s laid back stoner and Elwood’s manic straight edge would make for a top-notch double act.

Can I stream it on Netflix? No. It’s available for purchase at Chill.com.

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

Elise Czajkowski is a freelance journalist in New York City. She really would love to go on tour.

Going on the Road with Doug Benson in ‘The Greatest […]