Diamond Teeth Mary McClain
Singing for the Lord, on the darker side of town.
@ Tobacco Road
(Miami’s Oldest and Most Notorious Bar)



Since it was taken (1986), the photograph of Mary McClain standing in front of Tobacco Road, with downtown Miami in the background, hung on the dark red walls of Tobacco Road’s upstairs, until the bar closed (after 103 years) in 2012.

1986  — Pete Gallagher was a well known Florida journalist, who had written for Cocoa TODAY, the Miami Herald, Tropic Magazine, and at the time of his adventure with Mary McClain, was writing for Chief James Billie’s Seminole Publications.

Once a member of Chitlin’ Circuit Royalty, and now, at 84, limiting her performance to occasional Sundays with the Church Choir.

Stepping Out
by Pete Gallagher
Alligator Staff Writer

It was four hours into a dark Friday evening when my battered red van stopped in front of Diamond Teeth Mary’s house. Her ancient Bradenton, Fla., neighborhood was sound asleep, a still portrait broken only by a sweep of leaves scratching up a snoozing street hound. I knew the world’s oldest performing blues singer was all packed and waiting inside, staring down some snowy late-late TV movie, and welling up with a mighty irritation over the fact that we were a couple of hours late. I knocked lightly.
The door opened and a small, grandmotherly woman quickly turned her back to me. Even the framed pictures of her mother, Bessie Smith and John F. Kennedy seemed to be muttering. Something about where in hell had I been. The Juicy Fruit foil on her gums glistened off a naked yellow living room bulb.

I pondered an explanation as we packed her ancient performing gowns into the van. Should I tell her we had a flat tire? Or take the easy way out and blame it on the Skyway Bridge? Or should I give her the truth and blame our tardiness on Octopussy?

Should I let her know that her band of gentlemen had performed country punk music under that assumed name Thursday evening in St. Petersburg? Would she understand that we were all broke and that was the quickest way we could earn enough money to make her performance in Miami? How could I tell her about Looney Larry Cole crashing his unicycle on a beer spill while playing his accordion in the pub? “He managed to save his accordion by breaking the fall with his arm,” I thought about saying, “which is why he can’t play drums with us tonight.”

Of course, then I would have to get into the whole incredible last-minute frenzy. I’d have to explain how the only drummer we could find was her 58- year-old son Yogi, a professional contortionist. She would understand how Yogi forgot his suitcase and how we had to wait 20 minutes while he banshee- screamed at his deaf girlfriend to open the door of his apartment (located above a tavern where drunken handgun shooting is popular on weekends).

The more I thought about it, the more appropriate it seemed to let Yogi tell her. Besides, this was all beginning to sound like one of Mary’s own tales about life on the traveling minstrel-show circuit. “I pulled Big Mama Thornton off a garbage truck and put her on stage for the first time,” begins one of her stories.

“. . . And there was my sister Bessie lying there dying, her arm mostly cut off, red blood dripping in an old pan. The white doctors in Mississippi wouldn’t treat her because she was black,” is the climax of a saga about her famous half-sister, legendary blues singer Bessie Smith. >>>

Mary was kicked out of her church for singing “the devil’s music.”


— dave.

New Band For The Ornery Lady

Erik Hokkanen was 17 years old when he was crowned the Fiddle Playing Champion of Florida, and had since moved to Austin, Texas. At the time of his meeting Mary, Erik was struggling to make a just-above-poverty living playing Country-Punk in roadside, and strip-mall across the Southeast, between Texas and Florida. (Mofro/Hank Williams III)


>>> NEXT TO THOSE STORIES, MY EXCUSES SEEMED A LITTLE FLAT. Sure, Erik Hokkanen the guitar player had to fly in from Texas and Obie the bass player had cut his fingertips in a saw accident and Blind Willie James the piano man had the sunglasses stolen right off his face. 

I knew it would all disintegrate on the burning ears of an 84-year-old woman who swears she has never been late for a job in 70-plus years of professional performing. Besides, no matter what excuse I gave, she would stay committed to an old blues tradition: blame it on the manager. Me.

“You know I’m always late, Miss McClain,” I said, giving her my best Jamaican cane-cutter glare. “You ride with Erik.”

I WAS A NEWSPAPER REPORTER WHEN I FIRST MET DIAMOND TEETH MARY SMITH DANIEL MCCLAIN. Researchers for the Smithsonian Institution and the Florida Folk Arts Program had discovered her, penniless and bored, in the little Bradenton neighborhood where she had retired in the early ’60s. No one in her neighborhood (including Clifford, the husband she married in Bradenton) had any idea she was anyone other than a hellacious voice in the Sunday choir. In truth, she was one of those surviving links to America’s rock-‘n’-roll beginnings, a headline performer at the Cotton Clubs of the day, the last of the original blues “shouters” who gave definition and precedent to the Aretha Franklins, Ella Fitzgeralds and Eartha Kitts of the next generation. With diamonds surgically imbedded in her teeth, she performed alongside all the greats, including Louis Armstrong, Big Joe Turner and Fats Waller.

HER REDISCOVERY WAS AN ANTHROPOLOGICAL MILESTONE; she was quickly invited to sing at prestigious festivals such as the American Folk Festival at Wolftrap (Washington, D.C.) and the Florida Folk Festival (White Springs). An elegant octogenarian with facial skin smooth as silk, she captivated stunned audiences with a vocal range and inner fire that belied her age.

Mary McClain was national caliber, I deduced. So I gathered all the background material I could find and began booking her at nightclubs and festivals around the state.

MY IMPULSE HAD TURNED INTO AN OBSESSION. Soon she had a band and a regular income, was hired to star in an off-Broadway musical and began filming a documentary movie. But, just as the Diamond Teeth Mary express began to cruise, it derailed. She was kicked out of her church for singing “the devil’s music,” her handicapped husband died, bill collectors began to hound her, her faithful band broke up, she kept losing money and purses, and was forever forgetting to pay her phone bill.

During this period, Mary was the subject of numerous ill-fated promotions, including shopping center gigs and a concert to raise money to “put the diamonds back in Diamond Teeth Mary’s mouth.” The crowning blow came last year when she was spirited to Europe, where a trio of backers began knocking on bistro doors for work. But the effort to achieve overseas stardom failed, and finally the blues legend was shipped back to Bradenton, no richer than before.

My reputation smarting, my bank account depleted, my time wasted and my bitterness acute, I swore I would never associate with Diamond Teeth Mary again. True, I had learned a lot about the blues from Mary McClain, especially about the various abuses she and other black performers experienced in those cruel yesteryears. She was, I figured, an old dog that had simply been kicked too many times.

But, man, that dog could sing! And that was the dilemma.

WHEN THE TOBACCO ROAD NIGHTCLUB CALLED, I WAS OUT OF WORK AND COMMITTED TO STAYING AWAY FROM MARY. I knew the place. Located near the South Miami Avenue bridge, it has Miami’s liquor license No. 1 and serves the best late- night food in South Florida. Upstairs is a concert room unchanged from the pre-war era when “The Road” reigned as the city’s premier speakeasy. They wanted Diamond Teeth Mary to perform on an upcoming weekend.

Something stirred within my soul. It was like the feeling a compulsive gambler gets when he is thrown into a casino. What ghosts, I mused, could this electric old woman awaken from the red felt walls of Miami’s oldest bar?

The odd rationalizations, the lucid shots in the dark, the attractive maybes began to bombard my senses: Perhaps the old lady would gain the attention of some wealthy South Florida sheik. Maybe Larry King would be in town and catch her show. She would be great on Miami Vice. I called and gave her the club’s offer: a couple of hundred bucks and a motel room.

I knew she would be dying to perform. Still, she remained in character: suspicious, mysterious and manipulative – three qualities gleaned during her first few years in show business (she ran away at age 13 to join a circus and masqueraded three years as a man). “That’s all we get for Miami?” she spat, the first substantial sentence she had directed toward me in more than six months. “We were getting a thousand dollars a night there back in 1932.”

Truth was, the few hundred bucks and the motel room was their top offer. “That’s what we gave Mose Allison and John Hammond,” said the club’s agent.

So we negotiated. Mary wanted to know if they would give an advance. The club said no. She allowed as she might do it and warned me that agents like to rip off black performers. “All right, I’ll do it,” she agreed finally. “Can you bring me some rhinestones for my fingernails?”

THE TWO-CAR Diamond Teeth Mary caravan pulled into Miami at 10:30 a.m. on “gig day” after driving all night and morning. Though the band and I were blue-blind paralytic bleary, Mary looked exactly as she had when we left, wrapped in her fur, gum foil sparkling in the sunlight. We arrived at the motel where the club had made reservations. Located on Dixie Highway in the teeming gut of Miami’s most active streetwalking district, the motel lacked one room for us. Without thinking, I lapsed into a familiar routine. My voice full of righteous indignation, I asked the woman at the registration desk, “Where is Mr. Charles supposed to sleep?

“Mr. Charles?” The woman searched the looseleaf notebook in front of her, then glanced behind me with a start. I turned and saw Blind Willie the piano man climbing out of the van to stretch his legs. Three hookers were talking to him. “Hey, Ray!” I screamed out the door. “Ray, hold on tight and we’ll have a room in a minute.”

Willie stood to attention, rolled his head back like Stevie Wonder and let out that uncomfortable throaty chuckle which always overtakes him when we pull the Ray Charles scam.

“Mr. Ray Charles? The famous singer?” The registration desk began to tremble. I learned a long time ago that nearly everyone is a Ray Charles fan. “My God, ma’am,” I responded, “we can’t have him and Diamond Teeth Mary in the same room. What would the National Enquirer say?”

That did it. A maid was summoned: “Tell the party in Room 5 he’s going to have to move out!”

IN THE MUSIC business we call it “The Hell Carry.” The sound equipment, including a full-sized upright piano, had to be carried up a nearly vertical fire escape – barely one person wide – all dinged and bloodstained from years of people tripping, I presumed, and falling (to their death, amputation or paraplegia) beneath huge speaker cabinets. A hurricane stabbing a paper straw into a palm tree is the only phenomenon which can compare with getting that piano upstairs.

Naturally, the piano went out of tune. The local tuner would not come down on a Friday to tune it. After all that work we had to borrow a tiny electric keyboard for Blind Willie to play.

Somehow, the show began on time. The club was packed. Like all of Diamond Teeth Mary’s shows, the excitement built as the night went on. She entered from the back of the room, singing This Little Light of Mine, weaving through the standing-room-only crowd until she reached stage center. Then she stopped the band and gave the practiced disclaimer that allows her to keep membership in her current Bradenton church. Blues singing is not something she does anymore since she became a Christian but sometimes “I am made to do some things I do not want to do,” she said, and moved her head in such a way that the entire audience glanced at the guilty-looking man standing behind the sound board. Me.

Then Mary wailed, “I hate to see-ee-ee the eve-nin su-u-un go down,” she wailed as the band kicked into St. Louis Blues. Strafes of Mary’s voodoo lasered through the crowd as she turned to direct the band, pointing here, pointing there, wiggling her hips in sultry ways that Whitney Houston could not conceive. Later, the din died to a whisper as she crooned an a-capella Amazing Grace, imploring the house sinners to join in on the “Praise God” final verse.

The audience swayed back and forth, mesmerized by Mary’s energy. She seemed to glow gold, like some Star Trek creature about to vanish. The walls began to loosen their hold on the ghosts of the blues past. My head felt light and I knew my eyes were high. Then when the thunder died down to mere applause, Mary began her finale: a rousing version of When The Saints Go Marching In.

As usual, she kept screaming, over and over and over, to “Turn the house lights on! Turn the house lights on!” The agitated crowd felt all over the walls for a light switch. The bartender tried to shout instructions but the din carried away his words. At least 10 people galloped downstairs to find the manager. Lighters began to flick. “Turn the house lights on!” Mary screamed again.

I went onstage and informed her that this particular “house” had no bright overhead lights to illuminate her exit. The guitarist squealed a note and Mary jerked back into action with a frightening breakdance. It went on like that until 5 a.m.

That kind of musical high, we all agreed later, must be why we do it.

IT ALL WENT away at 10:01 a.m. when a great door shaking commenced in my brain. I covered my eyes with the pillow. From within the cotton womb, I heard the phone ringing. It was check-out time.

When I opened the door, I stared in disbelief. There was Diamond Teeth Mary, wrapped up in her fur, standing with her bags next to the highway, all hunched over and unmoving. A police car was parked on the corner, surrounded by an entire squadron of stunned Dixie Highway hookers. I doubt they had ever seen anything like Diamond Teeth before. For a brief moment, the streets of Miami were clear of crime.

Back at the club, after everything was packed, my exhausted body was surrounded by a ballet or outstretched hands. The agent wanted $80; the equipment men got $40. So much for my profit as manager.

The bar was empty of all sheiks. Larry King was nowhere in sight. Sonny Crockett had never shown. The ghosts had been re-plastered behind the red velvet walls.

The Diamond Teeth Mary express limped home in a silence as absolute as the applause which had bellrung our ears the night before. I thought of a blues guitar player named Little Juke who loved to play with Mary because of all this pain and glory. The man used to exult in misfortune, embrace bad times, yearn for despair, because “That’s the blues, man.”

And, recalling the morning’s events, I thought, maybe Juke is right. Maybe that wasn’t really 84-year-old Diamond Teeth Mary Daniel Smith McClain, last of the great blues shouters, wrapped in fur though it was 80 degrees, silent in an air full of profanities, absolutely unmoving though the vicious wind of Miami traffic had dust-covered her ancient black high heels. No, that wasn’t Mary. That was the blues, man. And, by the grace of God, this blues woman has had it all her live long days.

— 30 —


— Miami Herald (1986)

The Miami Herald (Doug Clifton), unwilling to publish a photograph of Mary McClain, at Tobacco Road, walking down the narrow stairs, from the red room (bar and stage), with a bordello-like painting of a buxom, bare breasted, blonde woman, stretched out on the expected brass bed, but there was no problem with 16th Century weenies of the Renaissance.



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