Soul-Crushing R-Rated Comedy Will Break You If You’re Not Ready For It

Most stand-up fans will be the first people to tell you that comedy comes from a dark place. Just like being a musician, writer, or filmmaker, honing your craft requires a person to spend a considerable amount of time alone working on their art, which can lead to an expected level of social awkwardness or straight-up questionable behavior. It’s one of those things that comes with the territory, and you just have to be built for it.

Some people are able to assimilate better than others and live normal, healthy lives when they’re not on the road trying to get good and win over audiences across the country. Some people change for the worse, which is the subject of 2015’s Entertainment, starring Gregg Turkington as a somewhat subdued version of the Neil Hamburger character his act is built around.

If I had to compare Entertainment to any similar media, I’d point your attention to a two-episode run of Louie from the fifth season known as “The Road,” which tackles a lot of the same subjects, but without nearly as much heaviness. Don’t get me wrong, both pieces of media are total bummers, but they each have their own distinct flavor.

Despite its comedic backdrop, Entertainment is not a comedy, but rather a sad exploration of one man’s life as the road swallows him whole and he becomes a stranger to everyone he loves. It’s not afraid to show you just how lonely this kind of life can be, and Gregg Turkington deserves all the praise he gets here for leaning into the darker side of a life so many people would like to glamorize.

On The Road Again …

Entertainment tells the bleak story of a man known only as The Comedian (Gregg Turkington). We follow him from gig to gig alongside his opening act, known only as Eddie the Opener (Tye Sheridan). Like the Louie episodes, our protagonist is suffering an existential crisis, and “depressed” is his default resting state, while his hack opener is having a great time schlepping across the country and performing his set.

When The Comedian isn’t humiliating himself on stage with his questionable brand of humor met with silence, he’s watching soap operas in whatever run-down motel he’s staying at for the night and leaving voicemails for his daughter. As time passes, it becomes heavily implied that he has an estranged relationship with her because she never once picks up the phone.

During the day, The Comedian kills time by going on tours and carrying himself like an unpleasant person nobody wants to be around. The whole thing is a total bummer, but Turkington sells it. He’s simply going through the motions, whether he still wants to or not, because it’s the only life he knows. You can tell he wants something more fulfilling, but he sells the misanthropy and malaise so well that, as a viewer, you can also tell he’s pretty much a lost cause.

Great If You Need To Be Knocked Down A Couple Pegs

If there’s one piece of advice I’d give you before sitting down with Entertainment, it’s to make sure you’re ready for it. It’s an excellent film that’s executed flawlessly, made even better by smaller roles from John C. Reilly and Tim Heidecker (who also contributed to the screenplay). But I’d be lying if I said this movie wasn’t dark as hell. If you’re not in the best headspace while watching Entertainment, it’ll probably leave you worse off, and I mean that as a compliment of the highest order.

Having spent a considerable amount of my formative years consuming all the stand-up comedy I could get my hands on, Entertainment feels like essential viewing. It shows you exactly what happens when somebody who’s known for their jokes doesn’t find anything funny anymore. It’s a slow descent into misanthropy and nihilism that has the potential to put you in a terrible mood if you’re not ready for it.

But if you’re having too good of a day and think you can handle it, Entertainment is currently streaming for free on Tubi, and it’s a total bummer in the best kind of way.