Winky McG of 9 Mile

When I was struggling to find employment after college, I took a chance on a job as a life insurance agent.  The first of possibly three interviews went well, so I bought myself a navy blue pinstripe pant suit to look extra sharp at round two.  After acing the second interview, I went over to the mall where an elderly man sitting on a bench pointed out that we were wearing the same pants.  We walked a lap around the mall together, and then he bought me a Mrs. Fields cookie.  

The investment into my pant suit was already paying off.

After making it through the third and final interview, the final step was to actually get licensed.  This involved a week of classes that culminated with an exam that had to be passed.  Since the school was about an hour and a half from where I lived, my dad helped me find the perfect hotel to stay at while attending class.  By “perfect,” I mean dirt cheap and super close to the school.

I arrived on a Sunday night.  The gentleman working at the front desk was friendly but didn’t seem to speak much English.  I managed to check in and got to my room, which wasn’t at all impressive, not that I had expected much.  The room was very dark, which wasn’t helped by the fact that the lamp by my bed didn’t work.  I swapped a working bulb from another fixture to see if I just needed a bulb but then concluded that the wires dangling down probably had something to do with it.  I called the front desk, and our call mainly went like this:

Me: “I don’t expect you to do anything about it right now, but I just wanted to let you know that the lamp mounted on the wall by the bed doesn’t work.”

Him: “I bring you new lamp!”

Me: “Well, it’s mounted to the wall, so I don’t think you-”

Him: “I bring you new lamp!”

Me: “No, I just wanted to let you know-”

Him: “I bring you new lamp!”

Me.  … “Okay, thank you.”

Of course, I never got a new lamp.  I was just happy that by Tuesday, I was able to unjam the control panel door on the furnace so that I could turn on the heat and not have to sleep in my winter coat (February in Michigan with no heat is brutal).  The heat problem probably could have been fixed with a simple phone call to the front desk, but I’d already used all my nerve to let them know about the lamp, which accomplished nothing.  I had decided to just keep to myself after that point.

One night, I heard some yelling in Spanish outside my door.  I looked through my peephole just in time to get a fisheye view of someone getting punched.  

Yep, I’m just gonna keep to myself.

Friday morning, I checked out.  My day’s plan was to go to class, take the exam, and then drive back home.  I was feeling defeated and drained and unsure of myself.  I felt like I was not absorbing the information in my class, and most of my classmates were older than me and male.  What the heck was I doing?  Did I even belong here?  I feared I was going to fail my exam.

It had snowed the previous night, so I had to brush off my car and then scrape the ice off the windshield.  I had started my car to get the defrost going.  My CD picked up where it left off, blaring Ryan Adams’ cover of “Lovesick Blues.”  I was singing that song quietly to myself, while working on cleaning my car off.  “Well, I’m in love, I’m in love with a beautiful gal…”

“That’s what’s the matter with me!”

Apparently, I was not alone.

Shocked, I turned around and found myself facing a tall, thin black man with a huge, bright smile. Normally, I would have been embarrassed that someone heard me singing in public, but I was just so surprised by this man’s presence.  

“Heeeeeeeeeeeeeeeeeeey!” He smiled.  “What’s your name?”

I paused for a second.  “Um, Katherine…”

He continued, “I’m Winky McG of 9 Mile!”

“Oh, hi,” I said, wondering if I was supposed to know who he was.

“You know Eminem, right?”  he asked me.


“Well, Eminem made 8 Mile famous!  And I’m gonna do that for 9 Mile.  It’s not all about 8 Mile!”

“Oh,” I said, trying to think of more to say.

As if reading my mind, he continued.  “Some people think I’m crazy.  But I’m not crazy.  It’s good to dream, to have goals.  I’m gonna make something of myself.  Everybody will know my name.  I have the passion, the drive…”

He continued to ramble for a while, smiling the entire time.  Part of me still thought this guy was kind of nutty, but it was also really inspiring.  The more I listened, the more uplifted I felt.  I thought to myself, yes!  I’m gonna go crush this last day of class!  And I’m gonna ace my exam!  And I’m gonna be the best gosh darn insurance agent ever!  THIS IS THE FIRST DAY OF THE REST OF MY LIFE!  I AM UNSTOPPABLE!!

I told him that I needed to go, but it was nice to meet him.  He started walking away backwards from me, telling me to not forget his name.  He was going to be big someday, him and 9 Mile.

YES, I thought to myself.  SO AM I!  Well, minus 9 Mile Road.  Hey, why limit myself to a road anyway, right?  I can do anything!!

“Goodbye, Winky!  Thanks!  I will remember you!”


That was over 14 years ago.

I admittedly have Googled his name occasionally throughout the years, even trying different spellings.  Winkie, Winkee, Winkey.  McG, McGee, MacG.  But there’s no sign of him.  He might have just been a friendly weirdo who never spoke of such a name to anyone else.  I don’t even know if he had any talent.  I assumed he was a rapper, what with the Eminem and 8 Mile talk.  But he never rapped.  And I’d been too caught off-guard to ask.

Whoever this guy was, he lit a fire under me that morning.  I went to class and then easily passed my exam.  I felt like I was on the verge of something amazing!  His enthusiasm had filled me with confidence and gave me so much hope about my future.  I was positive that great things were ahead!

I failed at my job, finally quitting after working 60 hour weeks for 4 weeks and making no money, other than the penny that was deposited into my checking account to test the direct deposit setup.  I remember offering my boss a two week’s notice of quitting but also noting that I didn’t see how it was going to do him or me any good.  He told me I could just leave. After that, I got a job for the same clothing chain I worked for while in high school and lived at home with my dad for another two years while continuing the struggle to do better for myself.


I remember sometimes thinking about him, getting bitter at this total stranger for getting my hopes up about life.  But I also appreciated him just popping into my life for a few minutes and brightening my day.  He had effortlessly built me up, motivated me.  If Winky could have such an upbeat attitude about life, so could I!  What went wrong???

In retrospect, I probably shouldn’t have glossed over the fact that as I had driven away that day, I saw him peeing on the side of the hotel while screaming.