Letter From Milo: Working for a Living

Gary, Indiana, in the mid 1960s, was a booming factory town, a thriving rust belt city in the very early stages of oxidization. Its steel mills, foundries and auto plant worked around the clock, three shifts a day, every day of the year.

As a result of the three-shift system, many of the businesses in town – taverns, diners, groceries, bowling alleys, pool rooms, barber shops, pawn shops, beauty salons, movie theaters, used car lots, gambling dens, whorehouses and houses of worship – kept their doors open 24-hours a day.

The time of day meant nothing in Gary. The rhythms of daily life were regulated by the demands of the factories. Swing shifts were a fact of life and many of the millworkers had to adjust their inner clocks by eight hours every seven days, often resorting to uppers and downers to make the transition easier.

Fueled by alcohol, pills and the relentless ticking of the factory time clock, Gary was a wide-open town where the term “anything goes” should have been engraved on a plaque at City Hall. . It was a gritty, hustling, noisy, corrupt, smelly and often brutal blue-collar town.

And there was a time, in my mid-teens, when I thought Gary was the most exciting, stimulating and interesting place on earth.

My favorite part of town was the tavern district, a six-block stretch lined with taverns, poolrooms, diners and private “sporting” clubs. Money was the grease that kept the tavern district running smoothly. It paid for whiskey, drugs and women, and kept the cops and judges in blissful, lucrative ignorance.

It was a neighborhood where everyone had a hustle — including me.

When I was a teenager I discovered I had a minor talent for sketching and drawing and used this modest gift to develop my own money-making scam, which I called “tavern portraits.” Here’s how I worked it.

I would walk along one of the busy streets of the tavern district, poking my head in the doorway of every saloon I passed. I was looking for a victim, or, I should say, customer, someone willing to pay me for drawing their portrait.

I remember once making a few bucks at a place called Kaiser’s Old Style Inn. I found exactly what I was looking for, a stout, middle-aged woman sitting alone at the bar. Although the tavern was crowded, there were empty stools on each side of her, which was an ideal set-up for me. I stood on the sidewalk for a few minutes, rehearsing my pitch, then, taking a deep breath, I walked into the tavern.

“Hi pretty lady,” I said loudly, trying to make myself heard over the boozy chatter of the customers and the noise of the jukebox.

The woman looked up bleary-eyed from her drink. “What do you want, kid?” she asked, stifling a yawn. She looked tired and worn, as if she worked too hard, for too many hours, on too little sleep.

“I was just passing by and I couldn’t help noticing you,” I said, giving her my best smile. “Your facial structure is a perfect example…”

Interrupting my well-rehearsed sales pitch, she tried to brush me off. “Get lost, kid. You’re too young for me.” Turning back to her drink, she added, “Try again in a couple of years.”

Thrown off stride, I tried to recover my momentum. “You don’t understand. I’m…”

“Give it up, kid.”

“Wait, listen. I’m an art student and I was captivated by your classic…”

She looked up. “Art student? Where?”

“At the, ah, the, Triple A College of Fine Art, over in, ah, East Chicago.”

“Never heard of it.”

“Doesn’t matter,” I said, getting back on track. “The thing is, when I saw your face it reminded me of the ancient Greek and Roman statues of goddesses that I saw at the famous Love Art Museum in Paris, France. You’ve got the same classic bone structure and your profile is almost exactly the same as the Mona Lisa de Milo, one of the most famous pieces of art in the world.”

I could see that I had caught her interest. “You’re shitting me, right?”

“I’m absolutely 110% serious. As soon as I saw you I knew I had to draw your portrait.”

She stared at me curiously for a few moments, then, her eyes narrowed in calculation. “You’re saying you want to draw my picture, right?”

“That’s right. It would be an honor.”

She smiled knowingly. “And how much is this going to cost me?”

“Normally, for a portrait of this superior quality, I charge 50 dollars. But, like I said, I’m so captivated by your classic features that I’ll do it for five dollars.”

“Five dollars, huh?” She thought it over, then, after making me sweat for awhile, she agreed. “OK, why not. But it better be good or you won’t get shit.”

When I first started hustling barroom portraits, I made the mistake of drawing people as they actually appeared. What I discovered, soon enough, was that very few people are satisfied with their appearance. They want to be thinner, heavier, taller, shorter, darker, lighter, younger, older, handsomer, prettier – almost anything other than what they are. What they really want is a portrait of the way they would have looked had the world been a better, more equitable place.

It took me half an hour to complete the woman’s portrait. I could have finished in 10 minutes, but I wanted her to feel like she was getting her money’s worth.

I flattened the bump on her nose and smoothed out the wrinkles on her forehead, around her eyes and upper lip. I softened her thin lips and brought out non-existent cheekbones. I tightened her sagging jowls and reduced her chins by one. I put some color in her ashen, grainy cheeks and placed her close-set eyes a little farther apart.

While I was working on the woman’s portrait, I made it a point to talk to her. I had discovered a while earlier, that my models liked it when I talked to them. As I flattered the woman, telling her what a wonderful model she was, how pleased I was to be drawing her portrait, I could see she was becoming more interested. She sat up straighter on her barstool, asked me to stop for a moment while she applied lipstick and said she wished she had done something with her hair. She even bought me a Coke.

When I handed her the finished portrait, she stared at it a while then broke into a raucous laugh. “God damn, kid, I’ve never looked like that in my life.”

Thinking she didn’t like it and worried about my five dollar fee, I tried to salvage the situation. Maybe she’d settle for giving me three dollars.

“The thing about fine portrait work,” I said, quickly, “is not only getting the physical features right, but also capturing the inner beauty and spiritual…”

“That’s enough bullshit, kid,” she said, cutting me off. “I love it. It’s great. I’ve never looked this good in my life. Matter of fact, I might have it framed.”

Turning to the bartender, she called out, “Hey, Angelo, take a look at this.”

The bartender came over, glanced at the portrait, and said, “Damn, Helen, is that you?” When the woman nodded, the bartender leered at her. “You’re looking real good there, babe. What are you doing later tonight?”

The woman laughed. “Staying far away from you is what I’m doing tonight.”

“OK, sweetie, you want another drink?”

“Yeah.”

The woman not only paid the entire five dollars, she added a five dollar tip. As I thanked her and prepared to leave, she said, “Hold on, aren’t you forgetting something?”

“What?”

“You forgot to sign it.”

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