A Man Aims High with His Last Wish in ‘Dying to Do Letterman’

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 got into comedy for one reason and one reason only,” Steve Mazan explains at the beginning of Dying to do Letterman. “To live a dream I’ve had since I was 12 years old: to perform stand-up comedy on David Letterman’s show.”

So in 2005, when the 35-year-old Mazan discovered that he had an untreatable, inoperable cancer and might have only five years left to live, he rededicated his career to achieving that goal that had lingered in his mind since starting comedy seven years earlier.

It won’t come as a surprise that getting on The Late Show with David Letterman isn’t an easy process, and so in January of 2006, Mazan began his “Dying to do Letterman” campaign. He started a website and began asking people at gigs to write to the show, hoping that a grassroots effort would propel him onto the show. (It’s been known to work.)

That plot would be enough to fill an entire documentary, but it’s just the set-up for Dying to do Letterman. At its heart, the film isn’t really about comedy, or Letterman, or cancer. It’s a personal story about Mazan and his wife Denise, and the highs ands lows of their lives as they deal with careers, family, and disease.

It’s essentially an old-fashioned tale about a man attempting to achieve his dreams, but don’t let that put you off. Dying to do Letterman is an amazingly memorable and moving film. And in the same style as Exporting Raymond and Gnarr, the story has a strong narrative that builds a genuine tension as the story unfolds.

It’s also an accessible movie, not aimed particularly at comedy fans. It makes a point of explaining Letterman’s influence and status in modern comedy, as well as more technical elements such as the role of bookers in late night television. And with its focus more on Mazan’s personal life than his career, it slightly skews the reality of a life in comedy. After all, most comedians’ careers aren’t about achieving one particular milestone, but about the gradual build-up of a lifetime’s worth of material and experiences.

But that distance from the comedy world also gives the film an inspiring lack of cynicism. It’s doesn’t get into the well-trod comedy tropes about the difficulty of life on the road, or any of the grandiose navel-gazing that many arts documentaries tend towards. Instead, Dying to do Letterman is a grounded but inspiring view of what drives a comedian.

And so, in conclusion…

Is it interesting? It is. It’s an exceptionally compelling story, with a twisting and sometimes heartbreaking narrative.

What does it have to say about comedy? For all of the talk in comedy about the influence of Johnny Carson’s Tonight Show on the careers of young comics, Mazan’s film explores how the next generation of comedians where influenced by Carson’s protégé. In Mazan’s intervies with big names like Ray Romano, Jim Gaffigan, and Kevin Nealon, they all discuss how appearing on Letterman’s show was important both as a career and personal milestone.

Is it funny? Well actually, it’s pretty sad at times. The only comedy shown is clips of Mazan, and it’s often the same bits over and over as he’s working them out. It’s more a heart-warming story than a laugh-a-minute comedy.

Can I stream it on Netflix? No. You can request a screening of the film via TUGG, and it will be available on VOD on December 4th. More information is here.

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

Elise Czajkowski is a freelance journalist in New York City, though she’s currently somewhere over Ohio.

A Man Aims High with His Last Wish in ‘Dying to Do […]