linguistic:paraphrasing, structural:summarization, information:highlighting, structural:scholar_edition
1982–1998: Later career and final projects

Santopietro stated that by the early 1980s, Sinatra's voice had "coarsened, losing much of its power and flexibility, but audiences didn't care." In 1982, he signed a $16 million three-year deal with the Golden Nugget of Las Vegas.

Kelley notes that by this period, Sinatra's voice had grown "darker, tougher and loamier," but he "continued to captivate audiences with his immutable magic." She added that his baritone voice "sometimes cracked, but the gliding intonations still aroused the same raptures of delight as they had at the Paramount Theater."

That year, he made a reported further $1.3 million from the Showtime television rights to his "Concert of the Americas" in the Dominican Republic, $1.6 million for a concert series at Carnegie Hall, and $250,000 in just one evening at the Chicago Fest. He donated a lot of his earnings to charity. He put on a performance at the White House for Italian president Sandro Pertini, and performed at the Radio City Music Hall with Luciano Pavarotti and George Shearing.

Sinatra was honored at the 1983 Kennedy Center Honors, alongside Katherine Dunham, James Stewart, Elia Kazan, and Virgil Thomson. Quoting Henry James, President Reagan said in honoring his old friend that "art was the shadow of humanity" and that Sinatra had "spent his life casting a magnificent and powerful shadow."

On September 21, 1983, Sinatra filed a $2 million court case against Kitty Kelley, suing her for punitive damages, before her unofficial biography, His Way, was even published. The book became a best-seller for "all the wrong reasons" and "the most eye-opening celebrity biography of our time," according to William Safire of The New York Times. Sinatra was always adamant that such a book would be written on his terms, and he himself would "set the record straight" in details of his life.

According to Kelley, the family detested her and the book, which took its toll on Sinatra's health. Kelley says that Tina Sinatra blamed her for her father's colon surgery in 1986. He was forced to drop the case on September 19, 1984, with several leading newspapers expressing concerns about censorship.

In 1984, Sinatra worked with Quincy Jones for the first time in nearly two decades on the album L.A. Is My Lady, which was well received critically. The album was a substitute for another Jones project, an album of duets with Lena Horne, which had to be abandoned. In 1986, Sinatra collapsed on stage while performing in Atlantic City and was hospitalized for diverticulitis, which left him looking frail. Two years later, Sinatra reunited with Martin and Davis and went on the Rat Pack Reunion Tour, during which they played many large arenas. When Martin dropped out of the tour early on, a rift developed between them, and the two never spoke again.

On June 6, 1988, Sinatra made his last recordings with Reprise for an album that was not released. He recorded " My Foolish Heart ", " Cry Me a River ", and other songs. Sinatra never completed the project, but take number 18 of "My Foolish Heart" may be heard in The Complete Reprise Studio Recordings (1995).

In 1990, Sinatra was awarded the second "Ella Award" by the Los Angeles-based Society of Singers, and performed for a final time with Ella Fitzgerald at the award ceremony. Sinatra maintained an active touring schedule in the early 1990s, performing 65 concerts in 1990, 73 in 1991, and 84 in 1992 in seventeen countries.

In 1993, Sinatra returned to Capitol Records and the recording studio for Duets, which became his best-selling album. The album and its sequel, Duets II, released the following year, would see Sinatra remake his classic recordings with popular contemporary performers, who added their vocals to a pre-recorded tape.

During his tours in the early 1990s, his memory failed him at times during concerts, and he fainted onstage in Richmond, Virginia in March 1994. His final public concerts were held in Fukuoka Dome in Japan on December 19–20, 1994. The following year, Sinatra sang for the last time on February 25, 1995, before a live audience of 1200 select guests at the Palm Desert Marriott Ballroom on the closing night of the Frank Sinatra Desert Classic golf tournament.

Esquire reported of the show that Sinatra was "clear, tough, on the money" and "in absolute control". Sinatra was awarded the Legend Award at the 1994 Grammy Awards, where he was introduced by Bono, who said of him, "Frank's the chairman of the bad attitude... Rock 'n roll plays at being tough, but this guy is the boss – the chairman of boss".

In 1995, to mark Sinatra's 80th birthday, the Empire State Building glowed blue. A star-studded birthday tribute, Sinatra: 80 Years My Way, was held at the Shrine Auditorium in Los Angeles, featuring performers such as Ray Charles, Little Richard, Natalie Cole and Salt-N-Pepa singing his songs. At the end of the program, Sinatra performed on stage for the last time to sing the final notes of the "Theme from New York, New York" with an ensemble. In recognition of his many years of association with Las Vegas, Sinatra was elected to the Gaming Hall of Fame in 1997.