The Awkward Musical Comedy of Henry Phillips

When I catch up with Henry Phillips via phone, he’s at home in Los Angeles, getting ready to leave for a road gig and looking for new recipes for his web series Henry’s Kitchen. “That’s pretty much most of my days,” he says. Phillips, a classically trained musician-turned comedian, has been honing his awkward, downcast blend of standup and musical comedy for the last two decades. In that time he’s released four albums, starred in the semi-autobiographical cult hit Punching the Clown, and appeared on Jimmy Kimmel Live and Comedy Central Presents. Phillip’s new album, Neither Here Nor There (available in wide release today), captures him at his career best, a level of accomplishment that creates an interesting juxtaposition when held up next to the very character he plays onstage. We talked about his fascination with failure, his rocky relationship with music, and the effect that success would have on his stage persona.

I’ve been watching a bunch of Henry’s Kitchen episodes on YouTube. Do you actually enjoy cooking?

In 2011 I was at a particularly depressing point of my life, going through a breakup and sort of a stalled career. I was cooking a lot for myself as a bachelor. I don’t necessarily enjoy it, but every time I wanted to cook a dish I would go to YouTube and, for example, type, “How do you make chili?” I would see these obscure ones with a middle-aged guy in his attic, with a really crappy camera, going off on a diatribe about chili that he read on Wikipedia. I thought, “I’ve got to start making these myself.” I did the first one and all my friends liked it. The second one I did actually went viral. I was like, “Maybe this will be how I occupy my time in between waiting for the phone to ring for the big stuff.” I think it turned out to be a good idea.

There is always a problem in every video. Either you don’t have the right ingredients, it’s not plating well, or you have other people try it and they don’t like it. The general theme is somebody with an interest in a hobby that they consistently fail at. That’s a theme that you implement in a lot of your material.

That’s true. It’s a little bit cringe-worthy to some people. I’ve always liked it. Albert Brooks has always been one of my favorite guys. Modern Romance defined my sense of humor at that time. Completely clueless optimism. Trying so hard and failing miserably over and over again. Garry Shandling was another one. He was always the victim in his act. His face always looked so funny to me. It made me feel good. To a certain extent, that’s kind of what we’re all like. That’s how my whole act started in the beginning. I used to go to music clubs and perform songs that I wrote, singer-songwriter type of ballads, stuff like that. It was always funny to see every third or fourth performer at a music open mic be so hilariously pretentious, over the top, or sharing way too much personal information. I wanted to do a version of that where I was making fun of it. I started out doing the songs where, for the first minute and a half, you would think, “This is just another one of those guys doing a serious song.” But then it would take a turn. It was fun for me to watch the audience go, “Oh, I think we’re getting played right now.” All of the comedy things I do are based on seeing somebody try something and fail and then trying to express my version of that.

You used the phrase “cringe-worthy.” I enjoy embarrassment, for myself and for other people. I think humiliation is a place where we can find our truest selves. There’s a humanity to failing in front of people.

Absolutely. When somebody fails and they try to play it off like everything is cool, not only does that make me want to laugh harder at them, it also says a lot about that person. Failure is funny. I think earlier in my career I was a little bit afraid of showing that. But as you get older you’re sort of like, “What the hell? We’re all clowns.” No one wants to pay money to see somebody who has the whole world figured out and is just going to preach it to you. I mean, they do, but that’s like a motivational speaker or something. People aren’t laughing at them. I mean, I’m laughing because I think they’re weird, but…

You’re a classically trained musician, right?

Yeah, that was my whole thing. Ever since I was 8 years old I’ve been a guitar player. I learned classical guitar, went to music school, learned how to read music and charts, orchestrate, all that stuff. I do try to use it. It’s hard because it flies in the face of what we were just talking about. It’s not necessarily funny to have musical talent. But in my kitchen videos I’ve tried to use what I’ve learned about music, using lush orchestral arrangements for the silly and depressing videos I have. I try to create little outlets for myself. At one point in my latest special I go to the piano to sing one of the songs. I think that the nicer the piano sounds, the more it smashes up against the lyrics. That’s an important thing with musical comedy: you have to have a little bit of irony there.

Did you have much success as a professional musician, non comedically?

Not really. As a matter of fact, that’s why I was so excited when I started doing comedy. I was like, “I might have just stumbled on a way that I can actually hold on to my love of music and turn it into a career.” I had various cover bands that would play at various weddings and stuff, but we were slowly getting replaced by DJs. That was a thing back in the early nineties. It was impossible to get somebody to pay even $300 for a band. Some people are doing it well, but I certainly wasn’t. In addition to being a failure at other things, I’m also not very good at business. That’s when throwing my hands up in the air and starting to do comedy at open mic nights became my thing. I was still hanging out with musicians, but then I started meeting a lot of comedians. Before I knew it I would be the opening act for a comedy club. My musician friends we’re like, “Wait, what happens?” I would say, “You just show up. There are already people there.” They couldn’t understand it. I was like, “They show up because it’s a comedy club. It doesn’t matter what your name is.” It was such a different scene. If you were a musician playing original music to 300 people you were probably famous or had a record deal or something. I gravitated toward the comedy thing right away because it looked like an opportunity for me to hold onto doing music, which was my first love.

Your comedy is not just musical. You incorporate a lot of standup. When you were making the transition from professional musician to comedy, did you go straight into musical comedy or did you try standup as well?

I had always been a huge standup comedy fan. It was always something I liked. It just wasn’t something I thought I could do. But when I started doing my act I would do a lot of filler in between the songs. Those sort of became actual jokes, more traditional standup. I was working with a lot of standups, pretty well-known and respected people, and they would tell me, “I really liked your joke about whatever.” I felt like I was a comic just like they were. But it wasn’t until at least 10 years in that I finally got the guts to put the guitar down and just go out and greet the audience and do 15 minutes of standup at the beginning, then pick up the guitar. That was a really conscious decision because when I was telling the jokes and holding the guitar I noticed that people weren’t listening as much. If you’re holding a guitar it always looks like you’re about to play it. Any information you say always looks like a lead-in to a song. I thought, “I won’t even pick up the guitar. I like these stories that I’m telling. I like these jokes. I’m going to get them out and then pick up the guitar and play music.”

A lot of people became familiar with you through Punching the Clown. You now have And Punching the Clown coming out. It premiered at South by Southwest. Is it available to view anywhere now? Do you have plans for wider release?

We’re in negotiations with a distributor now. These kind of things take a lot of time. I imagine if I was a household name and they made a call to the distributor and said, “Hey, Henry Phillips wants to do a thing,” they would say, “Okay, let’s do it next week.” But if you’re me, you just have to wait a long time because there’s a lot of trepidation. You don’t want to do it incorrectly. You don’t want to make decisions out of desperation. I remember signing a record deal way back when because I just wanted to get things out there. It’s one of the biggest regrets I’ve ever had.

What else do you have coming up that we can keep an eye out for?

I’m not sure how much I can talk about it, but let’s say that before the end of the year there will be some animation content that will be coming out. That’s a new world for me, but I think it’s going to work really well.

You built a stage persona that a lot of people describe as “hapless.” What happens if you continue to have success and you become more of a household name? Have you considered what that means to the character you created?

That’s a great question. I always thought that myself. I was always a big Tom Waits fan, but I was like, wait a second, “There’s no way that when Tom Waits is playing at The Wiltern theater he’s staying in some crappy hotel. What’s he going to write songs about?” I noticed that his stuff did change. He doesn’t sing about the same stuff he did when he was younger. But I think there will always be content. I would love to become successful enough to be able to ditch the essence of being a failure. That would be fantastic. I don’t see it happening anytime soon.

The Awkward Musical Comedy of Henry Phillips