Writing Jokes with Will Miles (The Knitting Factory, MTV)

My favorite rom-com is Forgetting Sarah Marshall.

[@MrWillMiles on Twitter]

What’s your name and where did you grow up?

My name is Will Miles and I grew up in Chicago, Illinois on the North Side.

What’s interesting or uninteresting about the North Side?

I grew up in Boys Town, a predominantly gay neighborhood, which is right next to Wrigley Field, where the Chicago Cubs play, and most known for having a lot of frat dudes around. My elementary school was between my neighborhood and the Cabrini Green Housing Projects, one of the most well known housing projects in the country before it was torn down. Growing up around all of these extreme differences made it hard to fit into an exact social group group, but it also made me a chameleon in terms of my friendships in life.

What did your parents do for a living when you were a kid?

My dad was a lawyer, politician, and is currently an investment banker. My mom worked in politics, was a nurse, and now works at an elementary school in the office. When I stop by her office, it appears the entire school relies on her in some way.

What was the first bit or joke you performed on stage?

The first bit I performed on stage was a bit about how one time I was high before bed with the Food Network on, and I dreamed about having a penis so large I could have sex with Rachael Ray in one room while being in the other room watching TV. It went over well at first, but I’m so happy it started bombing early on, so i had to stop doing it.

No-frills Boystown pub with an old-school jukebox & a weekly music & comedy open-mike night.

When and where did you become a regular?

The first places I became a regular were Town Hall Pub and Zanies. Town Hall Pub was a bar that used to have big punk and house-hip-hop parties with groups like Flosstradamus and Matt and Kim, and then turned into a comedy venue where I was a regular along with comedians like Jena Friedman, Beth Stelling, Hannibal Buress, and many more. One of my best friends, Julia, was the bartender during both the parties and the comedy shows. Zanies Comedy Club in Old Town is one of the oldest comedy clubs in Chicago. It’s my home club and Bert Haas is one of my favorite people in the world.

The Knitting Factory seems to be a great space for comedy. How did your relationship with them begin?

It originally began as a show hosted by Hannibal Buress, who I’ve known since before I was a stand up comedian. He built up the room for about five years and then got really busy so he handed it off to me, Clark Jones, and Kenny DeForest. We had all come and done it when he hosted throughout the years, and we moved here when he was ready to hand it off. I first did the show in about the second or third month it existed, so it was essential in my comedic growth over the last five years, as well. Its always been a great space and I love hosting with two of my best friends every week. We owe Hannibal a bunch for giving the show to us.

What do you like or dislike about the comedy scene in New York City?

I love the comedy scene because of the access to stage time. There are so many chances to work on your act in any given night. Even when network people or agents come to shows, they come because they are actually enjoying the process of stand up comedy. They even stay to watch the whole show. The only thing I dislike is the NYC open mic. I came from Chicago, where real people come to see open mics and you can get good responses from actual audience. In NYC, open mics are all comics, so its a little harder to judge what will work on a club or showcase stage.

Do you prefer forming jokes on paper or onstage?

I prefer building a skeleton offstage on paper but I have to work it out onstage to understand the punches and lock down the structure of what I’m trying to say. When I throw a new joke in the middle of a set, I understand my voice better and figure out the right word economy I need to make the joke funny. I read once that Louis CK starts with his closer when he’s developing an act, so I’ve been doing that. It really helps me write in my best comedic voice.

Any thoughts on where we are currently in the Drake-Meek Mill battle?

I love rap. I grew up listening to Pharcyde, NWA, Tribe Called Quest, etc, and my daily life is influenced by having grown up on that music. Currently, Drake has been completely destroying Meek Mill and will be the reason Meek Mill’s album sales drop from now on. I feel bad for how horribly he is treating Meek Mill, but I’d be lying if i didnt say I enjoyed watching it from afar. I mean, Drake got Will Smith and Kanye West to join in on the ridicule. That’s downright mean.

What are your three favorite romantic comedies and why?

My favorite rom com is Forgetting Sarah Marshall. I think it is a really great story about how when you try to make love happen, it’s probably the wrong choice, but when it just happens, you know in your heart that you’ve made the right choice. Every cameo is excellent and its a realistic journey to the “right one.”

This is why I also love “The Wedding Planner.” Beyond the fact that I think Matthew McConaughey is one of the best actors around, the Wedding Planner is a great story of how he was with the wrong woman but ended up falling in love with the his soul mate completely on accident. When you find your soul mate, its undeniable, and I think that really comes through in this story.

Three old friends — Mike (Omar Epps), Roland (Taye Diggs) and Slim (Richard T. Jones) — recount memories of their shared childhood in Inglewood, Calif., as they prepare for Roland’s wedding to his fiancée, Lisa (Lisa Raye).

My other favorite is The Wood. While it’s mostly a coming of age tale, the fact that Omar Epps’ character had to go through his entire life journey before he realized he has been in love with the same girl since the day he first laid eyes on her in 7th grade is a really beautiful love story. The supporting cast from the adults to the children really give their best performances, and the movie has always been one of my favorites.

Who is the funniest person you know?

My grandfather has never cared about saying the right thing, and that always makes me laugh. He is proof that if your intent is not to hurt someone, your words can still be very funny. He has a good heart, so I know he would never hurt anyone, but he also doesn’t watch what he says, and I laugh hard whenever he says things that could be taken as politically incorrect.

What’s the dumbest superhero name you can think of?

Asparagus Man

Why are jokes funny?

Jokes are funny because they are thoughts we wish we could have all the time. If everything could be looked at through a humorous take, life wouldn’t be so hard. Most comedians have at least a little bit of anxiety, narcissism, or depression, so looking at the humorous side of things is the way we cope internally and help others externally.


Will Miles is a comedian. writer. actor (truTV, Fusion, MTV2). friend of a friend. Knitting Factory every Sunday at 9PM.

Visit willmilescomedy.com


For more, follow @jokewriting on Twitter

Interview/Zuri Irvin (@withzuri)