No vocalist ever sang with more conviction, passion, and authority about love and romance than Francis Albert Sinatra. Outside a recording studio, concert hall, or nightclub, he was the ultimate paradox: kind, overly generous, and affable one moment, menacing, confrontational, and bullying the next. But when he sang, even those who cared little for him as a person were overwhelmed by the magnificence of his tone and the majesty of his sound.

Sinatra’s career mirrored changes in the American musical landscape: from the heyday of the big band and the ascendancy of radio through the rise of Las Vegas, the growth of nightclub culture, and the advent of television. He witnessed the recording industry’s evolution from 78s to 45s to 10-inch LPs and then 12-inch albums. And, like many of his colleagues, Sinatra had to adjust to the rock ’n’ roll revolution.

His finest numbers were written and arranged by America’s premier tunesmiths and wordsmiths, among them Cole Porter, Harold Arlen, Johnny Mercer, and Jule Styne. It’s no accident that numerous Sinatra staples were originally written for films or theater; to render a song effectively, he had to feel the lyric and act it out mentally. It makes sense that Sinatra would become a fine screen actor; his best tunes were often little scripts in which he played the starring role.

There was occasionally silly controversy over whether Sinatra was a popular vocalist with a jazz influence or whether he was a true jazz singer. He didn’t scat or improvise wordless lyrics, and he didn’t place much emphasis on the blues in his approach, though Billie Holiday was among his favorite singers. (Others included Bing Crosby, Ella Fitzgerald, and Mabel Mercer, as well as pals Dean Martin and Sammy Davis Jr.) But no one with Sinatra’s taste, love for big bands, or intuitive phrasing could not be classified as a jazz singer.

His appeal transcended era, age, gender, and race. Performers as different as Miles Davis, David Bowie, Bobby “Blue” Bland, Jack Jones, B.B. King, and Smokey Robinson all professed ardent admiration for his music. Spike Lee once astounded a group of film critics who’d come to interview him at his home by having a Sinatra album playing in the background.

Born in Hoboken, N.J., Sinatra first started singing professionally in the late ’30s, working at the Rusty Cabin nightclub in New Jersey. He later appeared alongside Dinah Shore and Dennis James on WNEW-AM in New York City, where trumpeter and bandleader Harry James heard him in 1939 and subsequently hired him to be his “boy singer.” A year later, he bolted James’ orchestra to join Tommy Dorsey. He cut his first hit single, “I’ll Never Smile Again,” and made his first public appearance at New York’s Paramount Theater.

While with Dorsey, Sinatra perfected many of the elements that made his work so unforgettable. He learned the secret of circular breathing, which enabled him to sustain notes, hold tones, and glide across lengthy passages and progressions with ease. His intonation and enunciation became impeccable. He didn’t simply mouth words or fake emotions—Sinatra made the audience believe in what he was singing because he never chose a number he couldn’t render with credibility.

By 1942, Sinatra was already an icon, too popular to be contained within a big band. When Jack Benny introduced him as a solo act at the Paramount, the screams and cries of young female fans signaled the rise of the bobby-sox era, not to mention Sinatra’s ascension to the ranks of romantic superstar. He continued scoring hits throughout the ’40s and became a regular on the syndicated Lucky Strike Hit Parade radio program in 1943.

In 1949, a vocal cord hemorrhage coincided with declining record sales for the singer; Mitch Miller, the head of Columbia Records, Sinatra’s label at the time, openly questioned whether he would ever be successful again. But by 1953, Sinatra was on the rebound: He joined Capitol Records, releasing a series of spectacular singles and albums. On each of his long-players for the label, he embodied the essence of swing, charm, irony, and arrogance, and he even helped to pioneer the art of the concept album. In 1953, he also purchased a percentage of the Sands hotel in Las Vegas, where he would eventually become the most popular performer in the city’s history.

In 1960, Sinatra started his own label, Reprise, where he stayed for 30 years, even after he’d sold his interest in the business. He continued working with acclaimed arrangers and conductors, among them Johnny Mandel, Quincy Jones, Sy Oliver, and Billy May. Despite the onslaught of the Beatles and Motown, Sinatra remained a potent commercial force through the ’60s and into the early ’70s. He opted to retire in 1971, after producing Ronald Reagan’s gubernatorial inaugural ball. That retirement lasted only two years, however, ending when he mounted a classic television special, “Ol’ Blue Eyes is Back.” It was the first of several TV specials he’d make during the next two decades.

Even as Sinatra hit the ’80s, he proved to be a relevant and important performer. He opened the decade with a three-record set, Trilogy, which included one of his signature songs, “New York, New York.” His appearance in Maracana Stadium in Rio de Janeiro set an attendance record for a solo performance, attracting 175,000 people.

Sinatra again hit the charts in the ’90s, with the LPs Duets (1993) and Duets II (1994). To purists, the recordings seemed more like publicity stunts than legitimate works, particularly since none of the vocal duets were cut with both performers in the studio at the same time. But the first collection proved so popular that CBS commissioned Sinatra’s daughter Tina to film Sinatra: The CBS Mini-Series in 1993. In 1994, he received the Grammy Legend Award, but he suffered the indignity of having his acceptance speech cut off by time-conscious producers.

Throughout the course of his career, Sinatra was a multiple Grammy winner, and he won an Oscar in 1953 for his performance in From Here to Eternity. He was a good actor, but ultimately, his music will be his legacy. Nicknames are sometimes inaccurate, but two of Sinatra’s best-known tags were unerringly on the mark: “The Voice” and “The Chairman of the Board.” American music won’t be the same without him, and we certainly won’t see anyone like him again.

Selected discography

Frank Sinatra recorded more than 200 albums and over 1,400 songs in a recording career that lasted from 1940 until 1995. The following list is highly subjective, but if you’re looking for a good collection, any of these will do.

Songs for Young Lovers (1954)

In the Wee Small Hours (1955)

Songs for Swingin’ Lovers (1956)

Only the Lonely (1958)

Sinatra-Basie (1963)

Days of Wine & Roses (1964)

A Man & His Music (1965)

Sinatra-Basie: Sinatra at the Sands (1966)

Francis A. and Edward K. (1968)

L.A. Is My Lady (1984)