Henry Phillips: The Comedian Who Makes Cringe an Art Form

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There’s a very specific, very peculiar sensation one feels when queuing up a Henry Phillips video on YouTube, if you know what to expect. Here’s a man, standing in front of you in a poorly lit kitchen, with a sappily optimistic-looking expression on his face, but unmistakable fear bubbling up just under the surface. He’s going to try and cook something for you. And it’s not going to go well. What you feel, then, is anticipation and preemptive pity—the expectation of humor, but a simultaneous quickening of the pulse, because you know you’re about to witness something that is truly, uncomfortably, painfully awkward. That’s Henry Phillips’ wheelhouse.

The pain truly is the most important part, and it’s his commitment to uncomfortableness that separates Phillips from other self-deprecating comedians. Henry would never dream of stopping at simple self-deprecation—he’s not the subject of his jokes so much as the victim of them. His stand-up comedy and multiple web series, of which “Henry’s Kitchen” is the most notable, revolve entirely around punishing the characters he plays with awkwardness and resulting depression that go far beyond what a normal human being would be able to withstand. If you’re able to watch his videos without thinking “oh god, this is going to be bad,” then he’s off his game.

Phillips is a comedian who has been most visible in the last few years, but the roots of his performances stretch back to when he was a sincere singer-songwriter in the ‘80s and ‘90s. By the late ‘90s, however, a certain jadedness with the entertainment industry transformed Phillips’ act into one blending music with stand-up, singing satirical songs that parodied the singer-songwriters and folk musicians he once identified with.

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“I feel like that’s when I struck a chord with the frustration people feel,” said Phillips on the phone, in advance of the release of his new album Neither Here Nor There on Friday, Aug. 19. “Most of what I’ve been doing is trying to express failure, human failure, and laugh at it. That’s where my music act came from; I thought ‘Wouldn’t it be funny if one of these super sincere singers was up there, just giving way too much personal information away every night?’”

The comedian’s material works across multiple formats, whether he’s singing or telling more traditional jokes on stage, or appearing in bizarre YouTube playlets. They all contain the same quintessential “Henry” character that Phillips has carved out for himself, a man who is desperate for the barest affection or affirmation, but is the constant victim of both terrible luck and his own inability to read people and connect with them in a normal way. Both aspects of failure are captured wonderfully in his other web series, “You and Your Fucking Coffee,” a sequence of shorts where Henry simply plays himself, perpetually searching for the seemingly simple request of a cup of coffee while actively ruining the lives of anyone around him unlucky enough to be drawn into the vortex of despair.

Still, it’s definitely “Henry’s Kitchen” that has brought Phillips the most attention, along with his 2009 feature film Punching the Clown, which taps into experiences from his earlier musical career. The parodic cooking show, meanwhile, came about after Phillips stumbled onto similar shows via YouTube and was blown away by the pathos on display.

“I’ve never been a good cook, so I’d go to YouTube and watch videos, and there would be one that would just kill me; some middle-aged guy in an attic staring into his camera with a diatribe about what chili is and isn’t,” he said. “The real story for me is why does this guy feel like it’s important that he teach people something? What is happening in his life right now?”

That was about five years ago now, and Phillips has produced the series off and on ever since while continuing to write and tour, making everything from “Thanksgiving vegetable turducken” to his most recent “chutney cheese weenie bites,” always challenging commonly accepted standards of edibility and video production values. He estimates that almost half of the crowd at any of his current stand-up shows are people who were first exposed to him via Henry’s Kitchen, with no other knowledge of his career. It gives him the motivation to continue destroying his kitchen and dredging up new recipes in the name of executing them disastrously.

“It’s always the first time I’ve made something, what you’re watching on screen, so the unexpected really can happen,” he said. “I really don’t know what’s going to happen when I start trying to cut a tomato with a butter knife, but I assume it won’t be good.”

Phillips’ new album, meanwhile, catches him performing at L.A.’s Lyric Theater, in front of a hometown audience. It functions as something of a retrospective or best-of in terms of his material, especially in the songs, which collect some of the wickedly satirical and bawdy tunes he’s been honing on the road in the last few years. Even moreso, though, Phillips is proud of the opening segments of traditional stand-up comedy, which key into some of the same distilled moments of extreme awkwardness. He can take a simple exchange that he overheard—in this case, a guy at a wedding asking someone else “Hey man, I thought you died?”—and spin it off into territory that builds further and further into absurdity.

“I wish I could avoid the cliche, but most of that just writes itself,” he said. “More and more, I’m starting to feel the stand-up as my career progresses. I don’t know why, but it feels like a very pure form of expression. And I think it’s a perfect time to put out this album, because it encapsulates me at my best. I couldn’t be happier with it.”

Jim Vorel is Paste’s resident staff writer, and he’s a much better cook than Henry Phillips. You can follow him on Twitter.