Paring it down with Drew Michael

There is a punchline that really delivers at the end of this interview.

Don’t scroll down, jerkface. Read the informative, insightful, enlightening Q and A I did with Chicago-born stand-up comic Drew Michael and arrive at his final, funny line organically. That is how I wrote it and that is how you should read it.

Michael, who lives in New York City, and I discussed how much he wants to escape winter, what occasional failure does for personal progress and why the bio on his website is the best bio on any website, in my opinion.

Dive into the interview, follow Michael on Twitter and don’t forget The Best Tweet I Can Find In Five Minutes at the end.

TC: You’re headed to Los Angeles soon. Are you looking forward to some warmer weather?

DM: I am. The weather was kind of an incidental bonus. I was just setting up shows and I wanted to take another trip out there so it just worked out, but yeah, that’ll be fun. It’s fun to hang out there for a week or so.

TC: The Chicago and New York winters have been brutal from what I’ve heard and seen.

DM: I haven’t been outside today. (interviewer, Michael laugh because the interview began at 2 p.m.) You kind of have to sit in your apartment and really convince yourself that you want what it is you say you want.

TC: On your podcast about the Chicago comedy scene and the New York scene, you talk about how important failure, and not being afraid to fail, is to a comic’s development. Do you think that applies to people in all walks of life?

DM: Sure. When I talk about comedy, I apply it to my own life and how it has a lot of parallels to life, but I don’t want to necessarily speak for anybody (else). Life itself is a pretty creative endeavor. We’re kind of told that it shouldn’t be, that if you just follow the script everything will be OK, but creativity is uncertainty and that poses a threat to whoever is running this nonsense. In any sort of creative endeavor, you’re going to want to find out where your limits are and the way to do that, at the core, is not being afraid to fuck up or do something like, “Ah, I wasn’t quite ready for that” or “That was out of my element.”

TC: It’s almost like the first time you go to the deep end of the pool. You don’t know what’s going on there. It’s scary as hell, but once you get there and find out you can survive, it opens up a whole new world.

DM: The only issue with that analogy is you can’t fail there, because you’ll die. (interviewer, Michael laugh)

It’s part of figuring out what works for you and in order to do that, you have to be willing to fail. I get it. When I’m here in New York, or in L.A. especially, you have this idea that there are people watching and everything is an audition and there’s a lot of pressure on every single move you make.

You even see that with politicians or celebrities. People who are always in the spotlight no matter what they do. If they go get gas in their car, they’re in 16 magazines with pictures of them with hats over their heads. They have to sort of capitulate to what they know the public will accept. That’s why you get such canned responses and it’s very disingenuous because they can’t fail.

I think it is important to find environments where you can (mess up) because otherwise, you’re just kind of this caricature of yourself.

TC: Yeah, and that’s why, when you do find somebody who is an outlier — a public figure who isn’t afraid to speak their mind — they seem so different, yet all they’re doing is being themselves.

DM: If you see someone doing comedy and they’re saying something that sounds kind of crazy but they’re able to make it work for an audience, in my mind, that isn’t that crazy. What’s crazy about it is how far from our standard narrative it is. The fact that people are responding to it shows that it’s not that far from our own internal monologue.

TC: I’ve read some pretty good bios on comedians’ websites, but yours is definitely my favorite. Please tell me an actual ex-girlfriend wrote it or at least contributed to it.

DM: I think I’m going to leave that ambiguous because I like it. My mom has pretty strong feelings on that in one particular way so I’m going to leave it ambiguous, but I’m glad you enjoyed it.

TC: Your bit about love being the craziest drug is truer than most people are probably willing to admit. Does being in love change your material or affect the way you perform?

DM: You start a relationship with somebody and it’s intense and you’re like, “Holy fuck!” She’s an awesome person and you’re having the best time and we spend all day just staring in each other’s faces. When I’m feeling like that, that affects the way that I live, sure. You might see some slight shift in how I perform or how I’m prioritizing performing at all.

I’ve found my best comedy is when I’m not in a relationship. I’m kind of the best when I’m coming out of it, when I have some perspective on it and when I have time and the drive and almost the desperation — the need — to go out and turn it into something. It compels me to kind of uncrack whatever that experience was and share it with people in a way that is honest, relatable and I’m not pandering to anybody.

Are these answers meandering? I hope I’m answering your questions, but I just kind of talk about stuff. I could go on for three hours with one question and we’ll just end up with this weird, esoteric cloud.

TC: I think we’re doing fine. You’ve answered every question I asked and meandering is good because it gives me more stuff to write about.

DM: You pare it down however you want. Just don’t make me look like an asshole.

Here it is, The Best Tweet I Can Find In Five Minutes: