Tony Middleton: From Fighting to Singing

The sports heroes and the music of our youth have a particularly evocative hold on us as we grow older.

Recently, I was watching The Willows – one of the quintessential 1950s doo-wop groups – on YouTube. They were performing at a revival concert in the late-1990s, singing their signature song: Church Bells May Ring. I wanted to know more about their lead singer, Tony Middleton. So I Googled him.

And this came up: “As a teenager, he was working toward becoming a Golden Gloves boxer.”

That piqued my interest. A week later, I was sitting opposite Middleton at a diner on the east side of Manhattan.

Middleton was born in Richmond, Virginia, in 1934 and moved to New York with his mother in the mid-1940s.

“I used to fight in the streets all the time,” he says. “I didn’t look for fights. They just happened. Guys would bother me after school. Or something else would happen. That’s the way things were. There was always somebody fighting. I was good on the street. I picked up some moves. I had fast hands. Guys would say, ‘Nobody can beat Tony.’

When Middleton was sixteen, he began to explore boxing more seriously and started training in the basement of the Salem Crescent Church in Harlem. For the uninitiated, in 1934, the year Middleton was born, a 13-year old named Walker Smith Jr. began training in the same basement under the tutelage of George Gainford, who coached the Salem Crescent Athletic Club boxing team. Smith was later known to the world as Sugar Ray Robinson.

“I could fight,” Middleton recalls. “But I could sing too. There was a group called The Dovers. Someone told them, ‘This guy can sing.’ They asked me to join them, and I did. I couldn’t fight and sing at the same time, so I put fighting aside. I could have been a professional boxer. I really believe that. I was good at singing and boxing, but there are no regrets. The only thing I felt bad about was, after I quit boxing, I gave my equipment to a guy named Curtis. I don’t remember his last name. He died. His sister came and told me, ‘He’s gone. It’s your fault.’ I felt bad, but I didn’t see it that way.”

Middleton joined The Dovers in 1952. The group soon changed its name to The 5 Willows and, after one of its members left, to The Willows. Church Bells May Ring, which Middleton wrote and sang lead on, was released in 1956 and reached #14 on the Billboard Charts. It would have gone higher. But many radio stations in the 1950s wouldn’t play rock and roll sung by black recording artists, choosing to play white “cover” versions instead. An all-white group called The Diamonds recorded Church Bells May Ring for those who preferred the old order.

Middleton left the Willows in 1957 to pursue a solo career. He worked with numerous world-class performers and had significant roles in several major theatrical productions. Movers and shakers like Quincy Jones sought him out. He also sang with later incarnations of The Platters, The Crests, and several other groups from the Golden Age of Rock and Roll. Trivia buffs might be aware that, when Middleton was on Broadway in the musical, Purlie, his understudy was Morgan Freeman.Decades later, the Willows reunited and toured throughout the 1980s. There were occasional concerts until 2009. Middleton is their only surviving member.

Meanwhile, Church Bells May Ring is the equivalent of a world championship in boxing. It’s there forever. Middleton’s place in history is secure. It can never be taken away from him. And he can look back on a lifetime of extraordinary memories.

“Malcolm X used to preach on the street on a soapbox under my window,” Middleton reminisces. “I spent time with James Baldwin at a bar called Juniors in the Alvin Hotel and got to know Lena Horne. I ran with a lot of big people and liked being around, but I never made it my business to hang in their lives. I never played the game to stick with them. One time, I was playing a club called Dionysus and Frank Sinatra came in for the show. Another time, I was at the Rainbow Room to hear Duke Ellington and he stopped the show to introduce me. You remember things like that.”

There are also memories of boxing.

“I had a drink with Joe Louis at Wells’ Restaurant on 132nd Street and Seventh Avenue [in Harlem]. Just the two of us, talking at one o’clock in the afternoon at the bar. And I had a conversation with Rocky Marciano at the Copa one night when Sam Cooke was playing there. Rocky told me he didn’t want to fight Joe Louis. He said knocking Joe out felt like beating up his own father.”

“I liked Ali,” Middleton continues. “But I was skeptical about him in a lot of ways. When Ali and Joe Frazier fought, I was rooting for Joe. Joe was my man. We were together from time to time.”

Asked about Frazier’s singing, Middleton responds diplomatically, “Joe had a rough voice, but he sang with enthusiasm. And he had a good band.”

Then Middleton’s thoughts turn to boxing today.

“I watch boxing on TV now,” he says. “But most of the fighters get in the ring without knowing what they’re doing. They’re not trained the way they used to be and they don’t give what they should give. The last really great fighter I saw was Sugar Ray Leonard. He was the best since Sugar Ray Robinson, better than Ali.”

Singers, like fighters (and the rest of us), get old. At 83, Tony Middleton can’t hit the high notes the way he once did. But he still has an active career guided by his manager, Phyllis Cortese. And whatever else is on his calendar, he sings every Sunday at noon at the Kitano Hotel at 66 Park Avenue in New York, where he has been a fixture for ten years.

On a recent Sunday, accompanied by a bass player and pianist, Middleton sang a dozen songs at the Kitano’s “jazz brunch.” He began by introducing himself to the audience: “I’m Tony Middleton. I’m Kate Middleton’s uncle.”

That got a laugh. A dozen timeless standards followed.

Middleton’s voice is still strong. He has style. His timing is impeccable. And he puts his emotions into the lyrics, telling a story with each song.

When Middleton sings Almost Like Being in Love, one gets the feeling that he’s remembering a special person and there have probably been more than a few special ladies in his life. When he sings All of Me, the audience knows that he has been hurt after falling in love.

Jazz, blues, ballads. Middleton does it all.

“He has a sexy voice,” the attractive blonde sitting next to me said.

“There’s probably two thousand songs I can sing,” Middleton noted afterward. “But I can’t do them all in one show.”

One advantage to singing over fighting is that practitioners can do it longer. Tony Middleton has been singing professionally for 65 years. He has lived a long full life. And he’s still living it.

“Making people smile is happiness to me,” Middleton says. “I love singing. When I’m onstage, the audience belongs to me and I can make them happy. What I always wanted out of life was to have a place to live, pay the rent, be happy, and leave something for my children. I live in a house now [in suburban New York]. It has a yard. I own it. It’s nice to own something. I plan on being around for a long time. My mother is 106 years old and still here, God bless her. So get used to me. I am the way I am. Always have been, always will be.”

To hear Tony Middleton, click here: https://www.youtube.com/watch?v=Oa0HmlPR5k0

Thomas Hauser can be reached by email at thauser@rcn.com. His next book – There Will Always Be Boxing – will be published this fall by the University of Arkansas Press. In 2004, the Boxing Writers Association of America honored Hauser with the Nat Fleischer Award for career excellence in boxing journalism.

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