During the late 1950s and early ’60s, Sinatra frequently appeared on stage and in films with his close-knit band of friends known variously as “The Clan,” “The Summit,” or, most popularly, “The Rat Pack.” Peripheral members included actors Peter Lawford, Joey Bishop, and Shirley MacLaine and honorary member John F. Kennedy, but the core group was always Sinatra, Sammy Davis, Jr., and Dean Martin. The trio performed a largely ad-libbed act of boozy humor, captured well in a recording of a 1962 performance at Chicago’s Villa Venice nightclub, The Summit: In Concert (released 1999).

Although the Rat Pack’s Las Vegas act often reveled in racial and misogynist humor, Sinatra had a long history as an advocate for racial integration. His friendship with and championing of Davis (and other African American celebrities, such as Billie Holiday, Joe Louis, and Duke Ellington) was only one aspect of his early liberal politics. A staunch Democrat and supporter of Pres. Franklin D. Roosevelt’s New Deal, in 1945 Sinatra appeared in The House I Live In, a short film promoting racial tolerance that received an honorary Oscar. It also caught the attention of the House Un-American Activities Committee, and some historians trace the first rumors of Sinatra’s mob connections to this time, suggesting they began as a political smear campaign.

Throughout the late 1940s and ’50s, the singer and actor continued to support pro-Roosevelt politics and the Democratic Party. He served as vice president of the Hollywood Independent Citizens Committee of the Arts, Sciences and Professions, a liberal coalition in the film industry, and he hired writers who had been blacklisted as communists. In 1961 he performed at a benefit concert in Carnegie Hall for civil rights leader Martin Luther King, Jr.

It was also about this time that Sinatra generated even more controversy for his connections with organized crime. In retrospect, even his harshest critics now acknowledge that Sinatra’s association with underworld figures was largely one of involuntary servitude, but there is no question that his fraternizing with notorious individuals such as Sam Giancana eroded his fan base and jeopardized his political friendships. In 1960, at the behest of Joseph P. Kennedy, Sr., Sinatra acted as a liaison between Giancana and the Kennedy family during John F. Kennedy’s presidential campaign, in order to ensure votes for Kennedy. (Sinatra’s rendition of “High Hopes” also served as the campaign’s theme song.) Within a few years, however, the Kennedy administration launched its war on organized crime and disassociated itself from Sinatra, while Giancana, having lost a powerful political connection, did likewise.

Sinatra continued to associate with mob figures throughout the years (“If you sing in joints, you’re gonna know the guys that run them,” was Sinatra’s standard defense), but his association with Giancana was perhaps the most publicized.

The Reprise years and Republican affiliation

Sinatra founded Reprise Records in 1960 and was allowed to record there simultaneously with his Capitol contract, which expired in 1962. During the early 1960s, Sinatra recorded at a furious pace, releasing some 14 albums of new material during the years 1961–63. He still worked frequently with Riddle, May, and Jenkins, but new arrangers such as Johnny Mandel, Neal Hefti, and Don Costa contributed fresh ideas to his recordings. Sinatra’s prodigiousness during these years resulted in some quickly recorded albums of uneven quality, but there were also several classics on par with the best of his Capitol work. His two 1960s masterpieces, the Jenkins-arranged September of My Years (1965) and the partnership with Brazilian songwriter Antônio Carlos Jobim, Francis Albert Sinatra & Antonio Carlos Jobim (1967), rank among Sinatra’s greatest albums. He also had chart success during the decade with the hit singles “Strangers in the Night” (1966), “That’s Life” (1967), and “My Way” (1969). The last of these, written for him by Paul Anka, came to be regarded as his signature song, one whose lyrics captured the tumult and triumph of his life and career, although he famously grew weary of performing it. As the decade wore on, his output was increasingly marred by misguided attempts to capture the youth market or by questionable choices of collaborators.

Politically, Sinatra began shifting to the right, perhaps as early as 1970, when he endorsed Ronald Reagan’s reelection campaign as governor of California. Then again, Reagan had been an actor and was counted by Sinatra as an “old friend.” Within a few years, however, he was fully affiliated with the Republican Party. The instigating event is generally agreed to have been a Democrat-led investigation of his mob ties by the House Select Committee on Crime in 1972. At that time the singer was called to testify before Congress and denounced the accusations as a “character assassination.” The following year he performed at the White House for Pres. Richard Nixon. Later Sinatra supported Reagan’s presidential campaign in 1980, and his much-publicized friendship with both Ronald and Nancy Reagan was a significant component of that political era’s celebrity-studded glamor.

The mature years

By 1969 the rock-oriented “Woodstock generation” dominated the music market, leaving Sinatra to lament, “Nobody’s writing songs for me any more.” He announced his retirement in 1971, but by 1973 he was recording once again. In his last two decades as a recording artist, he chose his projects carefully and released only seven albums of new material. His voice grew increasingly gritty and coarse, the product of years of abuse from cigarettes and alcohol. But he had learned to turn vocal shortcomings into interpretive strengths, and some of his later recordings are among his most poignant. His well-regarded albums of later years include volume one of the ambitious three-disc Trilogy (1980), the ballad collection She Shot Me Down (1981), and L.A. Is My Lady (1984), which featured an all-star orchestra. He returned to the recording studio (and to his former label of Capitol Records) after nearly a decade’s absence to record Duets (1993) and Duets II (1994), which paired Sinatra with several contemporary popular singers such as Barbra Streisand, Luther Vandross, and Bono. Though not critical favorites, the Duets albums sold millions of copies and were Sinatra’s final recordings.

In addition to his curtailed recording activity, Sinatra virtually retired from films during his later years. He concentrated instead on live performance and gave hundreds of international concerts from the late 1970s, with his final public performance in 1995. Although he suffered from failing memory and various physical infirmities during his last few years, he remained a compelling showman to the end.

Legacy

Sinatra will probably always remain a subject of controversy, largely because of his association with crime figures and his often belligerent attitude toward members of the press. Of his artistry, however, there is little debate, and the more than 1,400 recordings he made during more than 50 years as a performer are regarded by many critics as the most important body of work in American popular vocal music.

In 2002 his album Songs for Young Lovers (1954) was added to the National Recording Registry, a list of audio recordings deemed “culturally, historically, or aesthetically significant” by the U.S. Library of Congress. He won nine Grammy Awards as well as a lifetime achievement honor (1966) from the Recording Academy. More than a dozen of his recordings have been inducted into the Grammy Hall of Fame. Sinatra was also a Kennedy Center honoree (1983) and received the Presidential Medal of Freedom (1985).

Almost single-handedly, Sinatra redefined singing as a means of personal expression. In the words of critic Gene Lees, “[Sinatra] learned how to make a sophisticated craft sound as natural as an intimate conversation or personal confession.” Beneath the myth and the swagger lay an instinctive musical genius and a consummate entertainer. Through his life and his art, he transcended the status of mere icon to become one of the most recognizable symbols of American culture.