Gregory Isaacs, reggae’s “Cool Ruler,” whose aching vocals and poignant lyrics about love and loss and ghetto life endeared him to fans of Caribbean music, died on Monday at his home in London. He was 60.

The cause was lung cancer, said his wife, June Isaacs, who lives in Kingston, Jamaica.

Cat Coore, the guitarist and cellist for the seminal reggae band Third World, has called Mr. Isaacs “the Frank Sinatra of Jamaica” for his elegant vocal phrasing. But as the singer’s friend and former manager Don Hewitt observed, “It goes further than that, because Sinatra was not a songwriter.”

Mr. Isaacs’s nuanced compositions eschewed sentimental cliché and boastful machismo in favor of a sensitive, even vulnerable point of view. But on songs like “Slave Master” and “Hand Cuff,” he revealed a more militant side.

“Gregory used to sit and go through his lyrics with a dictionary,” his wife, a secondary-school teacher, said in a telephone interview. “He was very clean with his lyrical content and his grammar.”

Born on July 15, 1950, in the rough Kingston neighborhood Denham Town, Mr. Isaacs picked up the nickname Jah Tooth after a policeman broke one of his teeth. Inspired by the American soul singer Sam Cooke, he got his start on a local radio talent show, “The Vere Johns Opportunity Hour.” He was briefly a member of the vocal trio the Concordes before making his name with the solo single “All I Have Is Love” in 1973. Although he established his own Jamaican label and record shop, African Museum, with his fellow reggae singer Errol Dunkley, Mr. Isaacs was later signed to the British labels Virgin and Island.

While true mainstream success eluded him, few recording artists in any genre could rival his prolific output. He recorded hundreds of albums’ worth of original material, starting in the ’70s and concluding in 2008 with his final CD, “Brand New Me.”

Mr. Hewitt said of Keith Richards of the Rolling Stones that when he was introduced to Mr. Isaacs, “he carried on like he’d met Jesus.”

Mr. Isaacs was best known for his 1982 release “Night Nurse,” on which he was backed by the renowned band Roots Radics, which he organized in the 1970s. His 1988 album “Red Rose for Gregory” proved that he was equally at home singing over the hard-edged digital rhythms of reggae’s dancehall era.

He was also renowned for his fashion sense; he performed in the 1978 film “Rockers” wearing a powder-blue tuxedo and black fedora. “He was always dapper,” Mrs. Isaacs said. “Very proud, very tidy, very laconic, a man of few words.”

But he could be an aggressive businessman, she added. “He always stood up for what he deserved in whichever way he could,” she said. “When it came to what was due to him, he had to get that. No ifs, no buts, no maybes.”

When he and his wife were arrested for illegal possession of a firearm in 1983, she said, “he took the rap so I could go free” and served time in Kingston’s General Penitentiary. He was also arrested repeatedly for possession of cocaine and struggled with addiction for many years.

In addition to his wife, he is survived by his mother, Enid Murray; a brother, Sylvester; 12 children; and a grandson.

In a 2001 interview, Mr. Isaacs reflected on his legacy. “Look at me as a man who performed works musically,” he said. “Who uplift people who need upliftment, mentally, physically, economically — all forms. Who told the people to live with love ’cause only love can conquer war, and to understand themselves so that they can understand others.”