The roads not taken: Owen Benjamin, Neil Hamburger offer wildly different visions of life on the road as a comedian

These last weeks of the calendar year can be delicate times for comedians.

Do you have family obligations? Do you not have family to go home to? Do you have to work on Christmas or New Year’s Eve? Are you forever scanning the Internet to see if your name pops up on a year-end list of reviews? No matter how you answer those, you may find yourself assessing, re-assessing and having your career called into question by friends, family and even yourself.

Two new movies may help refocus you, or at the very least offer a fresh perspective for you or your comedian friends moving forward into 2016 and beyond.

Owen Benjamin launched an ambitious idea last month called #60minutes7days, in which he asked friends and fans for new premises with the promise that a week later, he’d have written a completely new hour of stand-up material.

Benjamin posted the results in an hour-long documentary last week. 60 minutes 7 days ostensibly is about his effort, but really is more about the day-to-day business of grinding out a comedy career over the course of one’s lifetime. Heck, the first 12 minutes of his documentary (which he edited and narrated himself) tracks his life story leading up to his self-imposed joke challenge. By the time the Day 1 title card appears, Benjamin is off and driving, or sitting in his car after a show receiving notes and feedback from his new wife. By Day 3, we see Benjamin posting a Facebook video calling on fans and friends to upload their requests for topics he should write about. Various unknown fans and well-known friends chime in — including David Koechner, Sal Vulcano, Roy Wood Jr., and Kunal Nayyar.

Not everything goes well, or even as planned. Benjamin talks straight to the camera above his steering wheel in a parking lot after he has just bombed in one club show.

Other times, too, Benjamin allows his narrative to go off course in surreal tangents, diving deep into his psyche and the recesses of his mind as he contemplates his next career move. Or even just his next joke.

“I tried 60 minutes,” Benjamin concludes. “A lot of it was garbage.”

But he still learned a lot about himself along the way.

And then there’s Neil Hamburger.

Sometimes described as the ultimate anti-comedian, Neil Hamburger actually is a fully realized comedic character concocted by Gregg Turkington, who loves nothing more than to take down hack comedians while sporting a tux and toting as many drinks in his arms as possible.

What if Neil Hamburger continued living offstage, though? That’s the fever dream suggested in the new movie Entertainment from director Rick Alverson.

It opened in November in cinemas in New York City and Los Angeles, and can be found On Demand via cable/satellite, iTunes or YouTube wherever you are. In Entertainment, we find Neil Hamburger playing a hellish series of one-nighter gigs in dive bars, pool halls and other makeshift venues somewhere in the desert deep in inland California. In this world, Hamburger has an estranged daughter he’d desperately love to reconnect with, but the only things he finds to connect with on the road are tourist trap landmarks and a Mexican soap opera that plays on his motel TV.

Can Hamburger keep himself together, mentally and emotionally? Or will he suffer a complete breakdown before making it home to Hollywood?

“What’s different from my live performances was that we were seeing the offstage comedy world — one that was only implied in my previous work,” Turkington said.

Turkington and Alverson wrote the script with their mutual friend Tim Heidecker (of Tim & Eric). Alverson said he’s not a fan of stand-up comedy. “I’ve always found it kind of figuratively pornographic and insular. Even as a young Catholic boy I found it vain and repulsive, there was almost something dirty about comedy to me. When I saw Gregg perform for the first time as Neil Hamburger, I found an affinity with him because his act exacerbated and magnified all the things I found problematic about that kind of performance. It was liberating to watch him, and it felt indicative of everything we know about pop entertainment in America in terms of its history — the idea that it would reach a sad and exhausted state eventually. Also there’s a kind of disconnect between his character and the audience. But there’s also this simplicity in their exchange — the fact that an attempt is still being made, even though the performer doesn’t connect in the way that he used to.”

For his part, Turkington said Entertainment allows you to see inside the darker side of show business and performers on the bottom rungs of the ladder. Whether they’re just starting out and paying their dues, or on their way down from their career peak.

“The notion of low-level entertainment, where there are small bursts of acclaim and applause, situated amid shitty hotels and bars within barely rewarding circuits — there’s a flip side to what people think of as fame and Entertainment is situated in this realm,” he said. “You can be as famous as Tiny Tim and still play the smallest of bills, but people aren’t so aware of this side of show business. Performers are working this circuit for the love of it, even when there are real financial needs not being met, and I think this kind of circuit can break people’s spirits — especially if they are working hard while on their way down.”

Watch 60 minutes 7 days by Owen Benjamin on YouTube; Entertainment starring “Neil Hamburger” is available On Demand.

Sean L. McCarthy

Editor and publisher since 2007, when he was named New York's Funniest Reporter. Former newspaper reporter at the New York Daily News, Boston Herald and smaller dailies and community papers across America. Loves comedy so much he founded this site.

View all posts by Sean L. McCarthy →