Its a lot of ways Black dudes describe their best friend.

  1. My day 1
  2. My ace
  3. My nigga if I dont get no damn bigger
  4. My “brother from another mother”

All of them apply to my homeboy; comedian, writer, actor, nice guy, Will Miles. We’re both graduates of Whitney Young High School, Morehouse College, and have been telling jokes for roughly the same amount of time, yet the dividing line for us, as with many Chicagoans, are regions called the “northside” and the “Southside.” As a native south sider, I subscribe to a slightly pettier, confrontational, and “the-f**k-he-looking-at” attitude because of the environment I was raised in. That edge being exclusive to people from my neighborhood isn’t a simple conclusion for a middle-class Black Northsider like Will.

“I had trouble relating to my friends and family that grew up in housing projects like Cabrini Green…but I tried, but I also couldn’t relate to many of my white friends who lived in Lincoln Park…but I tried.” Between sips of Jameson and Ginger Ale, he adds.  “That whole era of my teenage years was like, me not fitting in. Its like that Earl Sweatshirt line “too white for the Black kids, too Black for the White kids. We first met during a rap cypher, you were rapping, and I was beat-boxing, every rapper needs a beat.”

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Thank God for hip-hop. And also thank God for people who don’t always have to be out front, but even that gets tired after a while. “I almost named my album “Guy in the Back” but I feel like I’m evolving more to the front of the room.”

He ultimately went with “Good Year” (Comedy Dynamic, 2016).

Will Miles “Good Year” Available on Amazon, iTunes, Google Play and out of somebody’s trunk.

“Because I had a good year. (laughs hard). I had gotten a writing job on the Chris Gethard Show, I moved in with my girlfriend, and I felt a turned a corner with my comedy, in addition to co-hosting Comedy at the Knitting Factory, one of the best comedy shows in the city, fuck it, country.” Will laughs a lot. Like, a LOT. It’s a bit of a trademark. He greets you with a welcoming disposition that makes people around him feel more welcomed, more important, and even more entertaining than they are with other people.

“I don’t think people know how many close friends I have lost to various real life shit. Some people respond with hostility, and Ive seen that lead to more violence, or more negativity in life. Its a different way to handle challenges. I smile a lot because I feel no need to be hard all the time. Im also high a lot. So I think there’s probably something there.”

Will and Giulia Rozzi not only date, but they run a podcast called “Hopefully We Dont Break Up” #bold #brave

Just when you think you’re going to crack through to a serious Will Miles, the former CPS teacher deflects back to the jokes. But nobody’s life is peachy keen. It would also be a little sociopathic to have NOTHING that pisses you off.

“I try not to dwell on it too much, but people get me fucked up all the time (laughs)  ‘if you live a certain way, then you’re not as black.’ Because I have a white girlfriend…and Ive seen this specifically from my barber…he was talking about Jordan Peele, and how he doesnt respect the ‘black lens’ of brothers who are with white women . But my lens is my lens, so I have the same Black lens, thought its shaped differently. So because [Peele] and I both fell in love with Italian Americans means ours is different? Theres a common misconception that still exists that says if you date a white woman, then all of a sudden you’re assimilating to THEIR culture, instead of a mutual appreciation of each other. I’m still the same person Ive always been.”

This I’m a witness to. In two decades of knowing Will, I’ve repeatedly seen him use comedy to defuse situations. Whether potential physical fights, to a young woman friend punching him in college over another girl, to the time during freshman orientation when we were caught with alcohol on “dry” campus and thought knew we would be expelled. “welp, college was the best three days of my life” he joked, as we were escorted off the premises by Spelman College police. The nigger stays ready with a punchline. Though Black men use comedy as a way to deal with the challenges of existing, that doesn’t mean it never weighs on him.

Speaking on raising children in this crazy world, he ponders “The biggest challenge right now is watching the news. If we have kids, our son or daughter will be Black and then the numbers will skew to my favor. But having children worries me because there will be parts he my girlfriend wont understand, two parts if we have a son. Thats the biggest concern.”

But we had a Black President, didn’t that make everything better?

“I think it was a mask to make it seem like shit is cool for us. But Black folks knew that racism still wasnt over because its so ingrained in society. It was just a mask. hopefully it inspires younger generations. I honestly never thought it’d be a Black President, but I was glad he ‘survived’ it 8 years. It was a good symbolic victory, because of the inspiration to future generations. I think no matter what, I’ll keep my unit strong. we’re all pretty strong and understand where we are in life.”

He also acknowledges his dad and brother as constant examples of how to handle whatever adversity he faces.

“My brother was like dad number 2. I could watch him. And my dad didnt sugarcoat anything. I know they both had dreams of the arts. But they had other inspirations and all I have is the art. My dads a lawyer because he enjoyed politics as well and became a lawyer. My brother had aspirations to be a teacher. Ive only ever wanted to be a comedian since as far as I could imagine. The attitude of the Black dude, a classic one anyways, is one of being resilient but not afraid to ask for help, specifically from the women in his life or significant others.”

“Three classic things: Dave Chappelle “Killin em Softly”, “Midnight Marauders” by ATCQ, and the Harlem Rennaisance.”

“I think we listen to Black women more, I  listen to an Italian woman a lot but I also listen to my mom a lot (laughs). As a society we should listen to Black women a whole lot more. They’re a hushed group of people. Within every movement, there are too many overlooked. The people I see on TV don’t reflect the people I know in real life, and definitely not the young dudes I used to teach (rapper Vic Mensa is one of his former students) Theres a backwards mindset I see from pundits and media figures and celebrities.”


What About Chance the Rapper and Vic?

“Chance is great. Vic is great. When they talk, I feel like every race listens. Thats important.”

What are you listening to?

“Thunderkat. Khalid. I love J. Cole. Saba. No Name is killin shit. and also DRAM.”

Whats next for Black dudes in entertainment?

“Black boy joy! (smiling), people having fun is whats next. Those people I mentioned are care-free and I feel like I fit into that, on the outside Im pretty happy. Its important to show young Black men that you can be happy and there’s nothing wrong with that. I saw too many of my friends try to be hard and it didn’t turn out well.”


Whats your message to young black dudes pursuing a career in the arts, which can be so risky?

“Follow your dreams and just be yourself. The main thing I got from Morehouse was I could be myself, and things will still be alright.”

Family Ties: Sister, Dad, Girlfriend, Nieces, Mom, Brother.

Sage advice from a guy who is not only enjoying another good year for himself, but between joints, being in love, and enjoying the fruits of working hard and having a positive attitude, wants everyone around him to have themselves a good year as well.