Vic Damone, a pop crooner whose creamy baritone and heartthrob good looks propelled his success at the jukebox and on screen in the post-World War II era, and for five decades more in nightclubs and concert halls, died Feb. 11 at a hospital in Miami Beach. He was 89.

The cause was complications of respiratory failure, said his son-in-law William Karant.

Mr. Damone lacked the outsize personality of fellow Italian American pop singers Frank Sinatra and Dean Martin, but he nonetheless flourished on a rung just below greatness. He made more than 2,000 recordings, as well as dozens of movie and TV appearances, and sold out live performances until he retired in the early 2000s after a stroke.

He made his professional debut at 17, tying for first place on the radio contest “Arthur Godfrey’s Talent Scouts,” and his 1947 recording debut heralded an enviable new talent. “If I had one wish,” Sinatra was said to have remarked, “it would be for Vic Damone’s tonsils. Vic has the best pipes in the business.”

Music critic Will Friedwald, in his volume “A Biographical Guide to the Great Jazz and Pop Singers,” attributed to Mr. Damone all the hallmarks of Sinatra’s early romantic balladeer phase — “the beautiful voice, the light clear sound, the precise articulation, the impeccable phrasing.”

What Mr. Damone lacked, in Friedwald’s view, was the lived-in vocal shading that Sinatra cultivated over a turbulent life of wine, women and ring-a-ding mischief.

It was not that Mr. Damone led a tumult-free life. He had several rocky marriages, including to actress Pier Angeli and actress-singer Diahann Carroll; he was once dangled out of a New York hotel window by a Mafia kingpin; and he struggled back from bankruptcy after being swindled by business partners.

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But Mr. Damone’s earnest voice could not match Sinatra’s wounded soulfulness or introspective depth, nor did he push the boundaries of the pop form with his sunnily delivered standards, hit-parade titles, show tunes and updated Neapolitan love ballads with syrupy orchestrations.

He never “stood for something beyond a voice itself,” Friedwald wrote. “He was part of an era; Sinatra created one.”

Mr. Damone’s early string of hits included “I Have but One Heart,” “Again,” “You’re Breaking My Heart” and “Angela Mia,” but he was especially known for the ballad “On the Street Where You Live” from the Broadway musical “My Fair Lady.” He also had top-selling records with title songs from movies such as “An Affair to Remember,” “War and Peace” and “Gigi.”

Mr. Damone was signed to Metro-Goldwyn-Mayer studios and appeared in lighthearted early-1950s musicals such as “Rich, Young and Pretty,” “Deep in My Heart,” “Hit the Deck” and “Kismet,” in the last as the caliph who sings “Stranger in Paradise.” In a rare departure from form, he took a supporting role as a leatherneck in the 1960 World War II drama “Hell to Eternity,” co-starring Jeffrey Hunter and David Janssen.

The advent of rock-and-roll drove Mr. Damone from his perch atop the pop charts, but he made two of his finest albums during that phase of his career — “Linger Awhile with Vic Damone” and “The Lively Ones,” both in 1962 and featuring the singer at ease with jazzy, up-tempo standards such as “The Most Beautiful Girl in the World” and “Soft Lights and Sweet Music.”

Mr. Damone hosted two short-lived TV musical-variety programs and made a steady run of guest appearances on “The Andy Williams Show.” A favorite of President Ronald Reagan’s, he sang at the White House at least three times during the 1980s.

Mr. Damone — he took his mother’s maiden name — was born Vito Rocco Farinola in Brooklyn on June 12, 1928. As a singer, he accompanied his ­music-loving parents from a young age and took vocal lessons until his father, an electrician, was disabled in a workplace accident.

At 16, Mr. Damone left high school to support his family as an usher and elevator operator at the Paramount Theatre in New York, while aspiring to a career like Sinatra’s.

“I found the timbre of my voice was similar to his,” he told the Fort Lauderdale Sun-Sentinel decades later. “I was singing Sinatra songs to girls, and they loved it. I thought, this is what I want to do.”

After Mr. Damone’s triumph on “Arthur Godfrey’s Talent Scouts,” comedian Milton Berle helped him get an important nightclub date in Manhattan and a contract with Mercury Records. He sold millions of albums while serving a two-year Army stint in Germany during the Korean War.

With author David Chanoff, Mr. Damone wrote a memoir, “Singing Was the Easy Part” (2009), a title that alluded to his dramatic private life.

There was the hotel window incident, apparently provoked by Mr. Damone’s decision to call off an engagement to the daughter of a Mafioso. A sit-down brokered by Luciano crime family boss Frank Costello spared his life.

The singer subsequently squired screen goddesses including Ava Gardner. On one occasion, the usually teetotaling Mr. Damone downed at least four double vodkas to keep her interested. “Ava Gardner could make you do terrible things,” he quipped in the memoir.

In 1954, he married the troubled starlet Angeli, with whom he had a son, Perry. The marriage crumbled quickly, and Perry became the subject of a custody battle that drew international headlines. Years later, Angeli died of a barbiturate overdose. Perry died in 2014 from lymphoma.

Mr. Damone’s second marriage, to actress Judy Rawlins, produced three daughters but ruptured amid his bankruptcy in 1971. Two of his business partners had fled to Beirut with $250,000 from a bank loan he had co-signed.

He climbed out of the red through $25,000-a-week performances in Las Vegas. The dire need for income led him to turn down the role of singer Johnny Fontane in “The Godfather” (1972) — the part went instead to singer Al Martino — because of the comparably paltry compensation. It was not, in the movie’s parlance, an offer he couldn’t refuse.

Mr. Damone’s later marriages to Becky Ann Jones and Carroll (“Her priorities were show business, pure and simple,” he said) also collapsed. In 1998, he married fashion designer Rena Rowan, a co-founder of the apparel company Jones New York; she died in 2016.

Survivors include three daughters, Victoria Damone of Palm Beach, Fla., Andrea Damone-Brown of Dallas and Daniella Damone-Woodard of Scottsdale, Ariz.; two sisters; and six grandchildren.

Mr. Damone, long bothered by his lack of formal education, completed the coursework required for a diploma from his old Brooklyn high school in 1997. The same year, he received the Songwriters Hall of Fame’s lifetime achievement award.

He settled in Palm Beach County, Fla., focusing on his golf swing and practicing the Bahai faith that he said brought him “balance” in a profession plump with egos.

“You know, I never wanted to be a superstar,” he told the Palm Beach Post in 2009. “The entourage, four or five guys walking everywhere with me. None of that. I just wanted to pack up the bag, go to the airport and go do my job. I was happy with what I was doing.”