Frank Sinatra dies - May 14, 1998 - HISTORY.com

On this day in 1998, the legendary singer, actor and show-business icon Frank Sinatra dies of a heart attack in Los Angeles, at the age of 82.

Sinatra emerged from an Italian-American family in Hoboken, New Jersey, to become the first modern superstar of popular music, with an entertainment career that spanned more than five decades. In the first incarnation of his singing career, he was a master of the romantic ballads popular during World War II. After his appeal began to wane in the late 1940s, Sinatra reinvented himself as a suave swinger with a rougher, world-weary singing style, and began a spectacular comeback in the 1950s.

In addition to his great musical success, Sinatra appeared in 58 films; one of his earliest was Anchors Aweigh (1945). Playing a cocky Italian-American soldier who meets a violent death in From Here to Eternity (1953), co-starring Burt Lancaster and Montgomery Clift, Sinatra won an Academy Award for Best Supporting Actor. His film career flourished after that, as he starred as Nathan Detroit in the movie musical Guys and Dolls (1955) and played a heroin addict in The Man With the Golden Arm (1955), for which he was nominated for the Oscar for Best Actor. He also starred in the musicals High Society (1956) and Pal Joey (1957) and turned in a memorable performance as an Army investigator in the acclaimed film The Manchurian Candidate (1962).

By the late 1950s, Sinatra had become the epitome of show-business success and glamorous, rough-edged masculinity. He even headed up his own entourage, known as the Rat Pack, which included Sammy Davis Jr., Dean Martin, Peter Lawford and Joey Bishop. The group had originally formed around Humphrey Bogart, who died in 1957. The Rat Pack first appeared together on the big screen in 1960’s casino caper Ocean’s Eleven. They would go on to make Sergeant’s Three (1962), Four for Texas (1963) and Robin and the Seven Hoods (1964). Onscreen and in real life, the Pack’s famous stomping grounds included Las Vegas, Los Angeles and New York (notably the Copacabana Club).

Sinatra worked steadily in film throughout the 1960s, though many of his performances seemed almost perfunctory. His last major Hollywood role came in 1980’s The First Deadly Sin. A famous heartthrob, Sinatra married four times, divorcing his longtime sweetheart Nancy Barbato after a decade and three children (Nancy, Frank Jr. and Christina) to marry the actress Ava Gardner in 1951. Their marriage lasted less than two years, and in 1966 Sinatra married the 21-year-old actress Mia Farrow, 30 years his junior; they were divorced in 1968. In 1976, he married Barbara Blakely Marx (the former wife of Zeppo Marx), and they remained together until his death.