IN ENTERTAINMENT, there are few people who are successfully able to mix comedy and music. Henry Phillips stands as one of them: a comedian and singer/songwriter who has blurred the line and made a niche of his own in the comedy world. Having begun his journey eighteen years ago, the comic has become a heavily favored touring act for both his spoken-word material as well as his songs. His 2009 film, “Punching the Clown,” remains one of the purest, most truthful stories of the traveling comedian. It is also praised by many of those within the industry.
Phillips talks to TSJ about his music, “Punching The Clown,” and how the line between comedy and song has begun to fade today.
The Smoking Jacket: Obviously your background is music — did you start out as a singer/songwriter?
Henry Phillips: I always wanted to be a musician. Earlier in life it was rock music and then it was a singer/songwriter approach. I was always a fan of comedy too. I never thought I would actually do it. But the musicians that I hung out with – and I don’t know if this is true of all musicians – they were some of the funniest people. We’d crack jokes all the time and encourage each other.
Eventually I started screwing around with some of my songs and my friends would push me. They’d say, You need to go to open mics and do it for people. For some reason they thought it would work. So I started doing that and all of a sudden I noticed something I had never noticed before with my music – people were paying attention. [laughs] So I rewrote some old songs and turned them into comedy songs. Now, here I am eighteen years later making hundreds of dollars a year doing it. [laughs]
TSJ: [laughs] So did you notice they weren’t paying attention or did you really start it all for fun?
HP: It was completely for fun. I think every decision I made throughout my twenties was based on how I could have the most amount of fun with the least amount of expenses.
TSJ: That’s a good way to think about it.
HP: I never thought about having a career but it ended up happening. A few years into it I started getting radio airplay in LA and got a little bit of a following. I also started meeting other comedians who would bring me out as their opening act. That’s when it started becoming a career.
TSJ: Were they other guitar comics?
HP: No, usually stand ups enjoyed bringing me out because I wasn’t really stepping on what they were doing. It was sort of a fun interlude, doing music.
TSJ: Have you found that people tend to give shit to comedians who use instruments?
HP: Oh, yeah. That was especially common when I started. I’m noticing it less and less now. Every once in a while there’s something that pops up but not as much. Doug Stanhope, he was a good friend, he didn’t want to watch my act for three years because he just assumed it would suck. He didn’t want to be friends with somebody who sucked. [laughs] Eventually he saw it, it made him laugh, and he invited me to open for him.
I think that stereotype was built on when people are lazy and they use that guitar or instrument to bail them out of writing funny material. I do think it’s ironic that there’s a market out there for music and a market for comedy and by combining them both I wound up pissing off both sides. Musicians don’t like comedy music much and comedians don’t really like musical comedies so that was a struggle. But there are people who paved the way. There’s Tenacious D or Flight of the Conchords, all these great musical acts; they’re basically doing musical comedy.
As soon as people try to lay down rules about stuff like that it always winds up getting broken. And that’s what you realize as you get older, saying something like, Well, I hate musical comedy. It’s almost like saying you hate impressions or juggling. Like, you mean it’s impossible for somebody to make you laugh if they’re doing those things? It’s such a bold statement to make for no reason.
TSJ: Because of all that, did you ever think about putting down the guitar and just picking up the mic?
HP: Yeah, I’ve always wanted to do that. And the reason is because I feel like when I’m holding the guitar, doing stand up-type stuff, I feel that just because I have the guitar sort of takes away from what I’m saying. Everyone assumes it’s just a filler bit in between the songs. So the last couple of years I’ve made a concerted effort to start my sets with jokes and stories, like stand up, because that’s an art form I also love. If I do that with a guitar, I can’t seem to sell it as much.
TSJ: I’m not trying to kiss your ass here, but I think your film “Punching The Clown” might be one of the best films I’ve seen about stand up. It shows the difficulties of the road but also the importance of it.
HP: That’s great! Thanks man! Well, there’s a couple of things I think we did accidentally with that film. We always enjoyed the script and were so excited when we were making it, but I think there’s some things we did that we might not have known we were doing, and the director might disagree with me here. People say write what you know. So everything from the beginning to the end is just a recreation of a conversation or a real thing that happened to me in life. Of course we’d exaggerate things like the bagel situation. I wasn’t railroaded out of LA for being a racist but the funny start was true. I think we ended up with a very honest movie. I actually lived it for fifteen years and I’m just retelling the story as opposed to someone who imagines what it must be like and then writes about it.
The other thing that came from it: most of the films you see about LA are about the big LA. Things like “Entourage” with major agents and movie stars and hot girls. I’ve never seen that world; I’ve never been a part of that. The only people I’ve dealt with have been small-timers. So here we have this movie where we’re saying I “make” it on a smalltime record label, everything in the film is small-time. That part wasn’t intentional; we were just trying to recreate these events. We just had realistic, everyman situations. Those power agents do exist; I just don’t know them.
“THE END OF THE WORLD”
TSJ: So since the film is pretty true, I have to ask if you performing in front of the Christian group actually happened…
HP: That’s a combination of a couple of things. I did a gig at a college in Texas. When I showed up I found out it was parents day, where parents come and check out the school. I didn’t know that. I also didn’t know that the school was a Christian school. I had one act at the time and I had to do an hour. So I knew I could do about twenty minutes of family-friendly material but after that nothing was suitable for kids or families. But they already paid me and I was obligated to do an hour.
I didn’t misrepresent myself; they had my CD’s and could have listened to them before hiring me but I guess they didn’t. It was a disaster! One lady said you were awful and you need to apologize to the woman who booked you. I found that odd because I was called and asked to do my act. That’s what I did. But I went back and this girl was crying. That’s where that story came from.
TSJ: You’d think they’d research the act they hire.
HP: It’s amazing how many club owners do not do that. If I owned a club I would watch an entire 45 minutes of whoever I was booking before I had them there instead of having them show up and realize they’re offensive to everyone there. It’s crazy that so many don’t do that.
TSJ: I remember when we met up in Boston, we were chatting about the road. Do you enjoy doing the road?
HP: I do. I feel like I’m getting a little tired of it at this point in my life. I’ve always enjoyed it and have always said that if I ever stop doing it I’d probably have to leave home once a month and take some trip to get away. There’s a part of me that feels like I need to get away to different locations, and the road helps me do that. That trip to Boston was fantastic for me. I’d never been and it’s really nice.
Doing what I do, I’ve gotten to see things that I never would have seen if I hadn’t become a comic. Things like Mt. Rushmore, I never would have seen that. But I’ve been, and I’ve seen Niagara Falls and all these other things. They’re things people do once in a life time but because I’m playing just outside of these places I get to go pretty often.
TSJ: That’s definitely a perk to doing the road.
HP: It’s a different world. And those people you meet at the clubs – you check in Wednesday and you’re there till Sunday – the staff and who you meet become your best friends for that week. And you’ll see them again the following year. When you’re in your twenties and thirties it’s pretty great because you just wind up getting friends from all over. And a lot of comics you talk to who are road veterans, there’s a certain awareness they have about people throughout the whole country, you know?
TSJ: Oh, absolutely. You guys actually see it.
HP: Exactly. You meet people firsthand. You meet single moms in their twenties or people who have worked for the same company their entire lives. You meet all walks of life in different places. I think you develop an understanding of people that a lot of other people don’t get if they are constantly surrounded by the same demographic.
TSJ: That’s true. You guys experience all of this firsthand. What we have is just what we read or hear or assume.
HP: Yeah! And we have to make all those people laugh, too. Lately, I think there’s more of a division of comedy across generations than there is geography. You and I were talking about Marc Maron before. If I go to Peoria, Illinois, everyone knows Maron if they’re under thirty or are a comedian. They’re of that age and demographic. And that’s the same in Boston.
It seems that that demographic is spread throughout the country, and I don’t know if it’s always been like that. I think it’s just because of the globalization of things, you know? In England, they watch so much stuff that it’s not even hard for an American comedian to do well. They are already onto our sense of humor.
TSJ: And I’d imagine things such as YouTube and the Internet has helped with that immensely.
“I think every decision I made throughout my twenties was based on how I could have the most amount of fun with the least amount of expenses.”
TSJ: In terms of the road, are there areas in the country that you enjoy working in more so than others?
HP: Now that I’ve been doing it for so long, I like to pick and choose. When I was younger I was excited to be anywhere, didn’t matter if it was Evansville, Indiana, or the San Francisco Punchline. Now I’d rather just spend a week at the San Francisco Punchline. [laughs] And that is nothing against Indiana; it’s just me getting older. There’s a little more to do in a place like San Francisco.
And when I got to make the trip where I met you, I played Boston and New York, and that was just incredible. To actually perform in New York was great.
TSJ: There is something to cities, I think most would agree. Especially if that city is prone to have good comedy, places like New York, Boston or San Francisco.
HP: Yeah, exactly. But the only thing I don’t like, and I think a lot of comics would agree, the club matters more than the location. Sometimes you have clubs in the same city that cater to different audiences. It can be a mismatch. You could be in New York or New Jersey but if that particular club has a clientele that are used to a certain kind of comedy or have gotten free tickets because the club was just trying to get a few drinks out of them to make money, that’s not going to be too great. You won’t get comedy fans.
I don’t want to mention club names but there’s a very hip town in the Midwest where there’s two clubs. One, for some reason, every comedian claims it to be their favorite club ever and the other, everybody hates. It’s the same city but two totally different vibes. It’s people wandering in from the streets VS people who actually enjoy comedy. It’s a tough thing.
TSJ: That club that you’re speaking of, I would imagine the club owner has a great deal to do with it. That particular owner is a huge fan of comedy, they want good acts; they want good comedy audiences, people who will listen and such.
HP: It’s about who they cater to. There’s a lot of situations like that all throughout the country.
TSJ: You mentioned that people weren’t listening to you in the early days when you were going for that singer/songwriter dream. Now that you’ve built an audience, have you ever thought about doing an album that isn’t comedy?
HP: I’ve been thinking about doing that recently because I love music and every once in a while I would like to be taken seriously as a musician. But somehow or another comedy always creeps in there. I always try to make a subtle joke.
To me, serious music that works, it’s just got to be so incredibly good. A song like “She’s Always a Woman to Me” by Billy Joel or pretty much any early Dylan, all that kind of stuff is so good. If it’s that good then it’s worth not making any jokes. But for some reason, if it’s any less than that, I always feel: well, I’m probably better at making a joke version than doing the real thing.
I feel like I’m a satirist first and foremost, whether I’m satirizing music or comedy. I do these kitchen videos on YouTube that have this over-the-top music. I’m always pushing to get the funny out of it, I guess. But in short, no, I don’t think I’ll be doing any real serious music anytime soon. But I might get a little more subtle with it.
TSJ: I think I heard you mention something about Ben Folds once, saying his songs are often funny.
HP: Right. When I started listening to Ben Folds, like twelve or thirteen years ago, I started noticing there was a line that was being blurred between serious songwriting and comedy. They have songs like “I Want My Money Back Bitch.” The lyrics jump off the page. The musicians are aware of the jokes and I like that. I might go a little more for the comedy where as he goes more to the music, but it seems the line is being blurred, and I really, really like that.
TSJ: Is it harder for you to write the song or the comedy?
HP: I think finding the funny part is usually harder. I had to learn how to do it. With a song you’re used to repeating a chorus over and over. That makes it memorable. But you’d never say the punchline of a joke over and over again. It’s a difficult thing but I really love it.