Frank Sinatra, whose unique crooning style traversed several generations and who became an Oscar-winning actor, died Thursday night of a heart attack. He was 82.

Sinatra’s publicist said the singer was pronounced dead at 10:50 p.m. at Cedars-Sinai Medical Center. His wife, Barbara, was with him when he died.

Sinatra had a life punctuated by peerless success as a performer, but his off-screen behavior held almost equal fascination with the public. He was linked to Presidents as well as mobsters; he was an unstinting philanthropist who also had a reputation as an ungenerous womanizer and public brawler, especially with the press.

Sinatra was, in every way, a phenomenon. His monikers “Chairman of the Board,” “Ol Blue Eyes” and “The Voice” were as unmistakable as the expert phrasing that was the signature of his mellow baritone. He was an original who continually spawned imitators and whose style weathered numerous changes in popular tastes.

His careers had its peaks and valleys, but the lows were never as pronounced as the highs. And well into his eighth decade, even after his voice had long lost its luster and he had “retired” several times, Sinatra was packing auditoriums and nightclubs. The popularity of his more than 100 vintage recordings never waned, and his newer albums like “Duets” — the first of three albums teaming him with a wide variety of contempo singers — sold very well, despite heavy rock competition.

Novelist William Kennedy once wrote about attending a Sinatra concert: “A lifetime of staying young at center stage: how can anybody be so good for so long? … (He) fades down the stairs and out, and you follow him with your eyes because he is carrying the sound of your youth, the songs of your middle age.”

In his prime, from the ’40s to the ’60s, Sinatra was also a potent film star, winning a supporting-actor Oscar for his perform-ance in “From Here to Eternity” and capturing a best actor nomination for the harrowing drug drama “The Man With the Golden Arm.” Among his 58 films there were such standouts as “On the Town,” “Guys and Dolls,” “Pal Joey,” “High Society,” “Some Came Running” and “The Manchurian Candidate.”

Success did not come overnight for Sinatra, which in part explains why he was never able to fully leave his “mean streets” origins completely behind. Francis Albert Sinatra, the only child of Italian immigrant, was born Dec. 12, 1917.

Had it not been for Bing Crosby, Sinatra might have followed other careers, such as boxing or journalism (he worked as a copy boy for the Jersey Observer). But in 1936, he and his then fiancee Nancy Barbato saw Crosby perform at a Jersey City vaudeville house. The glow of the evening changed his life.

He quit his job, and with no formal training, he and three local musicians appeared on Major Bowes’ Original Amateur Hour (as the Hoboken Four). They took first prize which included a national tour with Bowes’ company.

For the next few years Sinatra performed for free on local radio stations and was paid $15 a week for a gig at a North Jersey roadhouse, the Rustic Cabin. In 1939, he married Barbato, with whom he had three children, Nancy Jr., Frank Jr. and Christina.

His career went into high gear when, for $75 a week, he joined Harry James, who was starting a new orchestra. He didn’t stay with James for long, soon becoming part of the vocal group the Pied Pipers for Tommy Dorsey’s orchestra.

Over the next three years, Sinatra’s popularity grew to rival that of his employer, after he made hits of such songs as “I’ll Never Smile Again,” “Night and Day” and “This Love of Mine.” Sinatra said he developed his unique style of phrasing, pauses and glissandi through listening to Dorsey’s trombone playing. “I figured if he could do that phrasing with his horn, I could do it with my voice.”

In his book “Sinatra,” published in 1984, writer John Rockewell wrote that “what gives Sinatra his distinctive quality and what makes it easier for him to declaim conversationally, is his vocal ‘edge’ — the focused sharpness of attack that defines every note. Unlike many singers, classical or pop, his voice rarely slips back into his throat.”

In 1942, Sinatra went from rising star to idol. His eight-week solo engagement at New York’s Paramount Theater created near riots of swooning bobby-soxers with lines of 30,000 girls outside the 3,500-seat house. And if some of it was orchestrated through hype and publicity, Sinatra more than delivered on his promise.

His popularity was solidified by his radio appearances on “Your Hit Parade.” After he appeared briefly as a singer in two films, Hollywood starred him in such RKO musicals as the 1943 “Higher and Higher” and 1944’s “Step Lively.”

MGM quickly bought out his RKO commitment for $1.5 million over seven years and starred him with Gene Kelly in 1945’s “Anchors Aweigh,” where he sang the Oscar winning “I Fall in Love Too Easily.” Most of what he followed for MGM was strictly lightweight: colorfully produced, but undemanding pics, like “The Kissing Bandit” and “Take Me Out to the Ballgame.”

By 1947 he was releasing a single a month and selling 10 million records annually, commanding royalties of $250,000 in ad-dition to $200,000 from films and almost $500,000 from his weekly radio program. Each personal appearance brought in a minimum of $25,000.

In 1949 he was reteamed with Kelly in one of his best movies, “On the Town,” adapted from the Leonard Bernstein/Comden & Green movie. But then Sinatra hit on a major career slump exacerbated by vocal hemorrhages. MGM dropped him and he began a tempestuous affair with Ava Gardner (whom he married briefly following his divorce from Nancy in 1951) marked by constant tantrums and public brawls with the press.

CBS canceled his two-year TV show (he would have another on ABC in 1957-58), Columbia Records let his contract lapse and even his agent, MCA, abandoned him.

Like a phoenix, Sinatra roared back with 1953’s “From Here to Eternity”; through his new William Morris agent Abe Last-fogel, he fought hard to get the role, even submitting to a screen test. (However, there were no dead horses’ heads in Harry Cohn’s bed, as was later suggested in a fictionalized version of the incident by Mario Puzo in “The Godfather.”)

Sinatra did practically beg the Columbia chief for the role of Angelo Maggio, which had already been cast. Eli Wallach, who had been set for the part, opted to do a Broadway show and Sinatra agreed to take the role for $8,000, a deep cut from his normal $150,000 per film.

The Oscar he won for the role threw his career back into high gear.

It was followed shortly thereafter by his searing performance as a drug addict in Otto Preminger’s 1955 “The Man With the Golden Arm.”

That same year, he appeared in “Guys and Dolls,” and the following year he was in “High Society” (with another Oscar-winning song, Cole Porter’s “True Love”). He walked out of the film version of “Carousel” right after shooting began.

By 1956, Sinatra was one of the top 10 boxoffice attractions in the country and he stayed there for the next four years. He held interests in a Beverly Hills restaurant, the Sands Hotel in Las Vegas (which reportedly only furthered his friendship with mafiosi types) and several musical publishing companies. By 1957 he was earning $4 million a year, more than any other entertainer.

He appeared in the ’57 tuner “Pal Joey,” followed by dramatic roles in Vincente Minnelli’s 1958 “Some Came Running,” and Frank Capra’s 1959 comedy/drama “A Hole in the Head,” which had the Oscar winning song “High Hopes.”

In the 1960s, after 10 years of recording with Capitol Records, Sinatra started his own label, Reprise, later selling his interest to Warner Bros. for $27 million.

Though he continued to star in films throughout the decade, few of them were well received, except for John Frankenheimer’s 1962 “The Manchurian Candidate,” and 1968’s “The Detective.”

Sinatra’s cocky persona was now coming to the fore, as can be seen in the self-indulgent “Rat Pack” films such as “Oceans 11,” “Sergeants Three” and “Robin and the Seven Hoods,” which featured his constant cronies Sammy Davis Jr., Dean Martin, Peter Lawford and Joey Bishop.

In all, he appeared in nearly 60 films, including his sole attempt at directing, the 1965 “None But the Brave.”

But the hit records never abated in the 1960s, even with the flourishing of rock ‘n’ roll and the onset of the British invasion.

“That’s Life,” “Strangers in the Night,” and most significantly, “My Way,” were huge bestsellers, both with those raised on Sinatra and a new generation more comfortable with Elvis Presley and the British bands. Three of his recordings won Grammys for best album: “Come Dance With Me,” “September of My Years,” and “Sinatra: A Man And His Music.”

In 1971 he suddenly retired, only to return two years later with the album “Ol’ Blue Eyes is Back” and a Main Event world tour. His 1988-89 tour with Liza Minnelli and Sammy Davis Jr. broke B.O. records, grossing $1.8 million for one night in Tokyo alone.

In 1990, he celebrated his 75th birthday with a CBS special and in 1992, after suing Kitty Kelly for her unauthorized bio, he allowed himself to be somewhat unflatteringly portrayed in a miniseries produced by daughter Tina. One of his last great triumphs was the album “Duets,” in which he sang with such contemporary greats as U2’s Bono, Barbra Streisand and Aretha Franklin — though he never worked in the same studio as any of his partners. The album spawned two sequels.

Sinatra never stopped touring and his audience remained loyal. When on March 6, 1994, he collapsed on stage from heat ex-haustion, the event was front page news. It came right on the heels of his lifetime achievement award from the National Academy of Recording Arts & Sciences, presented by Bono. Sinatra’s acceptance speech was interrupted by his handlers, who were afraid he would ramble and embarrass himself.

Sinatra was an avid Franklin Roosevelt supporter and continued to back Democratic candidates through most of his career. He was a close friend of President John Kennedy, although the President’s brother Robert, then Attorney General, later froze Sinatra out.

His fraternization with mobsters, Robert Kennedy believed, could tarnish the President’s image, especially since the Attorney General was on a crusade against organized crime. Sinatra shifted toward Republican candidates such as Richard Nixon and Ronald Reagan in later years.

His frequent public outbursts were dutifully recorded by the media, who were often the targets of his anger. However, Sinatra was a major philanthropist, raising, by some estimates, $1 billion. His causes included the Red Cross, Police Athletic League and the National Multiple Sclerosis Society. He also won numerous awards, including the Academy’s Irving Thalberg award for his charitable work and the Kennedy Center lifetime achievement award.

He is survived by his fourth wife Barbara (his third wife was Mia Farrow), his three children by Nancy and ….grandchildren.

Timothy M. Gray contributed to this story.