C.W. Headley

CW Headley is a stand-up comic and musician currently based out of New York City. It’s hard to choose which order to put that in to be quite honest, so let me say that again. CW Headley is a musician and stand-up comic currently based out of New York City. I first had the privilege to see CW perform stand-up years ago and was delighted by his ingenious timing and outstanding jokes. There is a part of me that knows he may even wince reading that statement for its boorish sincerity, or worse flattery, but that doesn’t deter me in the slightest. It’s a joy to watch him perform as he navigates audiences’ raucous laughter or even nervousness as he takes them through a world of his own design.

Later when he started incorporating his guitar into his act, it started with small with bits like “racist Bob Dylan”, who was a huge inspiration to him when he was beginning to play music. When I asked him who his other influences were he said, “Definitely Bob Dylan, the Pixies and I’d have to say Danny Brown, Courtney Barnett but mostly those two.” This marriage of folk, rock, and hilarious dark imagery are a signature for CW as he now pursues comedy and music in tandem. The two go hand in hand when you write lyrics like the following:

♫ I’ll get debt and probably Parkinson’s disease

I’ll lose my house and my motor abilities

Cause Michael J. Fox is gonna happen to me ♫

One of my favorite verses from “Old Cartoons”, which describes physical, mental, and emotional destruction over top of bright chords while mulling over the mundane repetition of life like a hybrid of “Blowin in the Wind” and “Waves of Mutilation”. Throughout each of these songs it’s apparent that CW is a very talented songwriter, his musicality shines through with progressions and riffs that are easy to overlook sometimes because of the irreverence of the subject matter. I wondered to myself how he approached these songs in terms of intent, did he classify them as jokes that are also songs? Or songs with jokes? CW responded,

“I try to do like everyone other one, so like the first song (on his latest album Tiny Aliens) is a song with jokes in it, and then “I Think Your Mom is Racist” is like a funny song. I try to do back and forth.”

That blend makes each song feel like a cocktail of sorts where the humor is the booze and the music is the mixer, some are stronger than others but it’s a good time either way.

The last two years has seen CW’s catalog grow with the release of his debut album last year “Holy Smoke: Mountain of DooDoo” and now the recently released Tiny Aliens. After listening to the songs and seeing him bring them to the stage as well, there’s a fantastic quality to how CW approaches performing his music on the record versus in front of a crowd. I went to see him perform on a stand up show and was delighted by the small pauses and punchlines he added to his set which consisted of 3 songs he shortened for a quick spot. The crowd quickly fell into a frenzy with each verse. We were all delighted by the jokes but if you’re really paying attention, you could see CW smoothly adding in small trills on his guitar. Details that feel like he adds in to make things more interesting for himself, and after he exited the stage I was lucky enough to sit down with him to talk. This is how it went:

Did you start playing music young or was this something you picked up later in life?

I was 15 and would just do like Jimi Hendrix covers. You know everyone was, you remember the Guitar Hero and Rock Band era. All of these 15 year olds were into these sexist 80’s bands for ten years. They didn’t know what they were singing, but the guitar just kind of stuck with me. Then over the pandemic I released an earnest music album and I hated it. I did like making music again though, so I thought if I could come back to it and make it funny that would be cool.

When you’re writing song lyrics is it different than writing a joke to you?

What I do is I’ll make a progression first and then I’ll listen back to it. I’ll write jokes to the song first, and then I’ll go back and put a melody to it.

So you’re just creating the framework for a good pop song…

And punching it up with jokes, yes. [We both laugh]

Do you find one more difficult than the other? Music or comedy?

I think performing music comedy is definitely easier, but I think writing them is a little harder because I do shows now and some of them are straight up music shows and I feel really insecure around real musicians a lot of times. Nothing is worse than when you’re on a show and somebody is like earnestly singing about like they’re dead mom or something. I go up there like, “Wack-a dack-a doo” (singing). I feel like a fucking asshole. It reminds me of a time when I was in high school, and it was a performing arts high school, and we had to do a presentation for the Day of the Dead on someone who died. This one girl did her dead mom, she made a poem for her dead mom. This other girl did a painting of her grandfather who died. I drew Batman for Bob Kane who had died like 20 years prior, and I went up last.

Do you find it different performing a song live for an audience versus recording it for an album?

Yeah, I’d love to do a live album one day. The things you can do with pauses and interactions, you can’t capture that with a regular recording. The hope is that you put out this studio stuff, that gets some attention and someone gives you money to make a live album instead of me giving my friend twenty bucks.

A lot of your songs play with ideas that are dreary but in a sunny way, is that a tone you look for?

I think being absurd is the idea, but even dramas and every good movie has to be a little bit funny or have a sense of humor about it. Then the other stuff people can interpret and take whatever they want to from it, while you try keeping it true to yourself.

When you post a clip of some of these songs, do you worry about how it will be received with little to no context?

It’s a tough thing, I used to post the full songs but a friend of mine told me people scrolling are going to see a four minute video and think, “I don’t want to deal with that.” It’s best shot you have though, and people are going to misinterpret but people are going to hear it. You have to think what’s the funniest part of this and just go for it. Hope that people understand you’re trying to be funny.

How do you know which parts to pick, are you just choosing your favorites?

That never works, ever. {Laughing] It’s always people who like it that make it work, so you have to go with something that kills every time. I’ve noticed the audiences and the internet are rarely on the same page also, like you’ll post something and think this is going to be a sure thing and it’ll totally bomb on TikTok or Instagram and vice versa. I think the audience’s sense of humor is different online then it is in real life.

Do you think that’s the difference between hearing something around other people versus hearing it by yourself?

I think you get a better sense of someone’s personality when you’re seeing them live. That’s another thing that’s so important to live performances that sometimes you can’t define something like “I know what this guy is about”, you know. Where online there can be that separation and you take the words for what they are and nothing else. Everything’s way funnier if you know the person for sure. Even in that 5 minutes of talking to people (on stage) ahead of time can make it funny, but you don’t get that online.

If aliens are real and you wound up abducted, but they let you leave a voicemail to Earth, what would you say?

I’d say that they’ve chosen me because apparently I’m the best human. Out of all of the other humans, I am the most moral man. That’d be my legacy, they can’t refute that. You can’t prove me wrong, what are you going to do, find and ask them?

Do you ever wonder how the song’s will age with time?

I think music comedy is tricky because most people will roll their eyes when they see it, but to me it has the most opportunity for lines and jokes. You can do something in between (verses), the music itself can be funny like I have a song called Dr. Leibowitz where I have this OCD line and I’ll do it eighteen times. You can play with the format so much, the other side is that it also has the highest potential to be really corny.

If you had to choose would you rather the jokes bomb or for them to feel this is your musical expression and just not care?

Bomb any day of the week. I’d rather them say the jokes suck instead of being heartbroken for me. I mean the show I did before this one was a music show, and I was three songs in and they were just kind of not reacting. As a comedian you do self-deprecating stuff to get people to laugh, but with music they don’t know that you’re kidding so it just looks like you’re having a meltdown.

I was trying to be funny the whole time, but to them this guy just went up there, whined about his girlfriend’s mom and then got mad at us. It really comes off like the portrait of a maniac.

**As we wrapped up the interview another comic came and approached us**

It’s good that he’s here, he’s also been a victim of my crazy insecurity. I sent him an early version of the album but he didn’t get back to me fast enough, he’s been my friend for years, I thought that he hated it so I blocked him on everything.

You know how people will always have stories about skipping out on something to go see a really famous band? What would you want someone to cut to come see you?

Probably a funeral I guess.. [We all laugh] You know that Berry Gordy quote, like he said he wants to make records where if you only have enough money for a sandwich or the record, you buy the record. That’s insane to me, but we could take it one step further. You loved your aunt, but you love my music more.

Later on I arranged the photos you see here, spending time with CW seemed to fly by as we talked about the story and Tiny Aliens having just come out. He did admit to being nervous about the interview, and even still he was extremely gracious with his time. I’m listening to the album as I write this, the track “Honey” plays as I type away on my keyboard. It feels like the end of an episode of television I lived and in a nice way I feel hopeful. This track has no jokes whatsoever, and I’m loving it. A single cocktail if you will. I can’t wait to see what’s next for CW Headley.