Of the more than 125 portraits that Bruce Elliott has painted of regulars at the Old Town Ale House, one of his favorites is of a friend named Howie Grayck. It took Elliott a long time to get it right: he finishes most of his portraits in a few days, but Grayck’s took more than three weeks. “I almost threw it in the garbage,” Elliott says. “He’s a real sweet guy. Everyone loves him. He always has a smile, but he’s got a certain sorrowful look. There’s a sad quality to it. It’s real elusive, and that’s what I was trying to capture.”

After struggling with the painting one day, Elliott decided to sleep on it. When he returned the next morning to his studio in Hyde Park he fiddled with the eyes and smile until finally the face on the cardboard looked like Howie being Howie: a middle-aged man with a receding hairline, a brow like a moon, an ample mustache, and big, dark, soft eyes, smiling like a boozy father during the last hour of his daughter’s wedding reception.

Elliott, 66, has been drinking at the Ale House regularly for nearly 45 years, and for the past four and a half he’s been painting the portraits of his fellow barßies that now cover nearly every inch of wall space there. But last year his stake in the place went from purely emotional to financial: he and his wife, Tobin Mitchell, an administrator for the Dolton school district in suburban Riverdale, took over the business from longtime owner Beatrice Klug, who’d fallen ill with cancer in 2004. (She died in August of last year.) Elliott and Mitchell were old friends with both Beatrice and her ex-husband, Ale House barkeep Arthur Klug, who’d died of a heart attack in January 2005. Shortly after he died, Beatrice bequeathed the place to Elliott and Mitchell on one condition: that they remain adamantly opposed to change. Aside from the ever-increasing mass of Elliott’s artwork on the walls, they’ve kept their word. They fix chairs instead of replacing them and allow nothing but jazz on the jukebox: Beatrice Klug once dated a roadie and joined him on a Rolling Stones tour, after which she refused to listen to rock music for the rest of her life.

Elliott and Mitchell have inherited a Chicago institution: the Ale House opened in 1958 and quickly became a favorite haunt for writers, journalists, artists, and performers at nearby Second City. Arthur Klug, along with a group of investors, bought the bar in 1971, and after a fire less than a year later it moved to its current location at Wieland Street and North Avenue.

Elliott began frequenting the place in 1961, the year the Klugs got divorced. He got to know regulars like Eddie Balchowski, a heroin addict who was a concert pianist until he lost an arm in the Spanish civil war. (Elliott’s portrait of Balchowski depicts him as he knew him, a gray-bearded old man shooting up, tightening a rubber-band tourniquet with his teeth.) He met Mitchell in 1977 and married her in 1983, and over the years the couple stayed close with the Klugs, who continued to run the bar together. Elliott and Mitchell’s daughter, Grace, thought of the Klugs as grandparents, and all three were frequently at Beatrice’s bedside in the months before she died.

Taking over the bar was a major transition for Elliott, who readily admits that he has avoided having a real job his entire life. “I pretty much decided when I graduated high school that I was not cut out for work,” he says. “I’m work-phobic.” Technically it’s Mitchell who owns the bar, handling duties like managing the books and scheduling bartenders, and Elliott’s name isn’t on any documents. He drove a cab for about a year in the mid-60s, but in 1967 he moved to San Francisco to join the antiwar movement. While there he enrolled at Berkeley, where he graduated with a degree in history in 1971, though he says the only place he’s ever employed his knowledge is in barroom conversations.

He’s a little circumspect at first when asked how he earned a living after college. “I just always seemed to have money in my pocket,” he says. When pressed, he explains that over the years he made money through “more than 30 personal-injury lawsuits,” gambling on sports, and liberally using credit cards. He also played a lot of golf. For 30 years he participated in money games nearly every day at the Jackson Park and Joe Louis public golf courses, and in the winter months he’d do the same thing down in Sarasota. With friends he played straight up; with strangers he hustled. He says he once took advantage of his prematurely gray hair and clipped a guy by posing as a 70-year-old with a bad hip and a hearing aid. On the tenth hole he doubled down and began bombing drives 280 yards up the middle.

Elliott says he cut all that out three years ago. His game was going downhill, especially within 70 yards of the hole; he wasn’t practicing enough, and he had knee problems. These days, by midautumn he loses interest in golf and hangs out at the bar or at his house, three blocks away. And he returns to his studio, abandoned in the warmer months, to start painting again.

Elliott was born on the south side and grew up in Downers Grove. He began painting when he was in his late teens, and he’s largely self-taught. What technical education he has he absorbed by sitting in the living room of a Hyde Park town house owned by surrealist painter Gertrude Abercrombie. An uncle of Elliott’s was part of Abercrombie’s circle, which included jazz musicians, writers, and assorted visual artists. Elliott recalls there was usually a party taking place when he visited. “She was a colossal alcoholic,” he says. “And she was mean. You couldn’t ask her any questions, but she would let you sit there and observe.” He picked up some basics from her, and also learned how to economize: Abercrombie would buy old picture frames at yard sales and flea markets, then cut slabs of Masonite to fit them. (Elliott does the same, though his surface of choice for his Ale House portraits is cardboard.)

His paintings explode with color like a parade on a feast day. Though most are straightforward portraits, some depict sordid, noirish milieus that approach the pornographic. He’s painted many ensemble barroom scenes and mock Ale House posters that depict the bar as if it were the Moulin Rouge–a tribute to Beatrice, who was a fan of fin de siecle French poster art. The people in many of his paintings have a sickly yellow green pallor to their faces, suggesting a cartoonish Toulouse-Lautrec.

“It’s hardly avant-garde,” Elliott says. “I know that. But I paint what I like and what I’m interested in. Faces fascinate me, for instance. There are a lot of great faces in this place. I think there’s a lot of truth in these pictures in that way.”

His portraits do not generally flatter. Full of crags, creases, lines, and bags, his faces are studies in the physical effects of spending large portions of one’s life in bars. Sometimes a subject will take offense when he hangs a new picture. Elliott describes a newspaper reporter who waited for years to see his likeness displayed. “The minute it went up, he said if we didn’t take it down he’d bring in his gun and shoot it,” he says. (Elliott took it down.) Another unhappy patron tore Elliott’s portrait of him from its moorings, threw it on the ground, and jumped up and down on it. “The picture survived,” Elliott says. “He was barred for a while, though. It takes me four or five days minimum to do one, so if you do that it doesn’t make me happy.”

Elliott sticks to his principles even when depicting his closest friends. In one painting, local comic and Ale House regular John Fox is chased by a woman wielding a baseball bat while a pair of policemen attempt to restrain her. “Lucky me,” Fox says while looking up at the painting, which hangs prominently above the bar. “Fucking Bruce shows up in his car right behind the paddy wagon, sees the whole thing, and memorializes it.”

Nevertheless, Elliott is badgered by regulars who want their portraits done. But he says he can only successfully complete a piece if he knows the customer well, and he doesn’t accept commissions: “It would be too much like work.” Tourists will sometimes enter the Ale House, take a liking to a picture, and make Elliott an offer–once for $5,000. But he’s too attached to his work to remove it from the walls, and he claims he has no ambition to show his oeuvre outside the bar. (His brother Scott is an art dealer in Benton Harbor, Michigan.) On a recent Tuesday morning, a regular sitting at the bar called out to Elliott. “Hey Bruce,” he said over his beer. “You ever thought about having an exhibit?” Elliott, on his way to the john, waved off the idea. “No,” he said, without breaking stride. “This is my exhibit right here.”

He paints every day when he’s not golfing, and once he finds his groove in the studio he can spend up to nine hours working. “Some days I’ll leave the bar at 11:30 in the morning and won’t get back till 9 o’clock at night,” he says. He works from photographs and from memory; if he’s having trouble with a portrait, he’ll occasionally come back to the bar to study the subject’s face. He picked up painting again about ten years ago, but only in the past four and a half has he pursued portraiture so prolifically. Mitchell suggested he do it as a way to extend the mural that has long adorned the wall of the tavern opposite the bar. Painted in the early 70s by local commercial artist Maureen Munson, it’s a group portrait of 68 Ale House regulars at the time.

“At least 70 percent of the people in that mural have to be deceased,” says Elliott. The Munson mural was part of the past, Mitchell argued. What about the people who were drinking here now?

Many of Elliott’s subjects too have died. One is Michaela Tuohy, a woman everybody called Mike. In the painting she’s wearing a prim business suit, and her hair is steel gray and styled short. It could be a portrait of an upstanding grandmother, but one eye is drunkenly shut. A cigarette dangles from her lips as she attempts to light it; you can almost see her fumbling with the Bic. In Old Town bars Mike had a famous mouth in more ways than one: she took great pleasure in verbal sparring and she often misplaced her dentures. Her sidekick at the bar was a man named Bill “Tracy” Berg. “The two of them together were just vicious,” Elliott says. “When they walked into a bar together, people would cringe.” Berg threw himself out of a window at Saint Joseph’s Hospital in the early 80s, after learning he had AIDS. Tuohy died of heart failure in 1998, at 61; she wasn’t alive to see her portrait.

“She had finally straightened out, kind of got her life together,” Elliott says. “She was working for the city at the department of special events. And she had money and her own place, really for the first time in her life. But she kept the pedal to the metal. Her doctors told her to slow down on the drinking and smoking, and that was not ever going to happen.

“The thing about bar life is this: lives tend to be a lot shorter. But on the other hand, there’s not a night in this bar I don’t have a huge belly laugh. That’s the trade-off. There will be health issues, there will be domestic issues. But then there’s the fun factor that people who live an extra ten years don’t necessarily enjoy.”

The portraits of some of those who’ve passed away occupy what Elliott calls the dead wall. Mike Tuohy and Tracy Berg are there, as is Lazar Vakulin, who died in August from complications following a stroke. Lazar was famous around the bar for burning a $1,000 bill belonging to a wealthy patron named Ernie Kahn after Kahn dared him to do it.

Nearby is a portrait of Hank Oettinger, a retired printer, outspoken leftist, and indefatigable writer of angry letters to the editor. Oettinger often wore handmade political buttons on the lapels of his Salvation Army sportcoats. His latest, from 2004, was his favorite: Redefeat Bush, it read. Elliott had known Oettinger since he started coming to the Ale House and he keeps an archive of his letters in the basement of the bar. “Hank was the gold standard of customers,” he says. “He drank every day till he hit 91, though the last year of his life he slowed down. But he still ordered grapefruit juice.”

Oettinger, who died two years ago at 92, didn’t like his portrait. He thought it was too small. But Elliott has put it in a prime location, in a corner of the dead wall near a bank of windows at the front of the bar. The sun pours in on clear days, warming the area. “This is where he used to sit,” Elliott says. “So I hung him here.”

Art accompanying story in printed newspaper (not available in this archive): Photographs by Yvette Marie Dostatni.