10 Things to Know About Frank Sinatra, Who Died 25 Years Ago Today (2023)

The great singer died on May 14, 1998. His music never will.

10 Things to Know About Frank Sinatra, Who Died 25 Years Ago Today (1)

Sunday (May 14) marks 25 years since Frank Sinatra died at the age of 82. That’s hard to imagine, because he remains an icon and a cultural force. His compilation Nothing but the Best reached No. 2 on the Billboard 200 in May 2008, a decade after his death. Jay-Z gave him a shout-out in “Empire State of Mind,” his 2009 smash with Alicia Keys: “I’m the new Sinatra, and since I made it here/ I can make it anywhere, yeah, they love me everywhere.”

Sinatra had major hits spanning 40 years, from “I’ll Never Smile Again” in 1940, which he recorded with Tommy Dorsey and His Orchestra, to “Theme From New York, New York” in 1980, in which he took a song Liza Minnelli had introduced three years earlier in the film of the same name and simply took it to another level. It became his final top 40 hit on the Billboard Hot 100.

Sinatra had four No. 1 albums on the Billboard 200 (which originated in 1956): Come Fly With Me (1958), Frank Sinatra Sings for Only the Lonely (1958), Nice ‘N’ Easy (1960) and Strangers in the Night (1966).

He topped the Billboard Hot 100 (which originated in 1958) twice — with “Strangers in the Night” (1966) and “Somethin’ Stupid,” a duet with his daughter, Nancy Sinatra (1967).

Sinatra won nine Grammys and an Oscar. His classic 1965 TV special Frank Sinatra: A Man and His Music won an Emmy for outstanding musical program, but he didn’t personally win for it and never officially won an Emmy. (I hate it when that happens!)

Here are 10 facts you should know about Sinatra.

  • He was the first artist to win the Grammy for album of the year twice — and also three times.

    Sinatra won the most prestigious Grammy with Come Dance With Me!, September of My Years and A Man and His Music. To this day, no one has won in that category more than three times, though Stevie Wonder, Paul Simon and Taylor Swift have equaled his record. (Swift could set a new record at the 66th Grammy Awards if Midnights is crowned the winner.)

  • He amassed seven Grammy nods for record of the year — which stood as the record for decades.

    Sinatra received seven Grammy nods for record of the year, winning once for the sumptuous “Strangers in the Night.” That was the record until Beyoncé set a new mark (eight nods) when the nods for the 65th Grammys were announced late last year.

  • He won an Oscar for a dramatic role.

    Sinatra won best supporting actor for a dramatic role in Fred Zinnemann’s From Here to Eternity (1953). Two years later he was nominated for best actor for another dramatic role as a drug addict in Otto Preminger’s The Man With the Golden Arm.

    He also received two honorary Oscars. He received a 1946 award for The House I Live In, a short in which he starred which called for tolerance of those of different faiths. This was a year before the Oscar-winning feature film Gentleman’s Agreement, which dealt with the same issue. In 1970, he received a Jean Hersholt Humanitarian Award.

  • He introduced three Oscar winners for best original song.

    He was the first to sing “Three Coins in the Fountain” (1954), “All the Way” (1957) and “High Hopes (1959), all of which won Oscars for songwriters Sammy Cahn and Jimmy Van Heusen. He also introduced four other songs that were nominated in that category but didn’t win — “I Couldn’t Sleep a Wink Last Night” (1943), “I Fall in Love Too Easily” (1945), “(Love Is) The Tender Trap” (1955) and “My Kind of Town” (1964).

  • He won his first Grammy as an art director, not a singer.

    Sinatra was the leading nominee at the inaugural Grammy Awards, with six nods. But his only win was as art director of Frank Sinatra Sings for Only the Lonely. History does not record if Sinatra was amused that one of the greatest singers who ever lived won his first Grammy for art direction. Let’s hope so.

    Sinatra had two of the five nominees for album of the year that year — Frank Sinatra Sings for Only the Lonely and Come Fly With Me. As a result, it seems likely that his support was split, which worked to the benefit of Henry Mancini’s Music From Peter Gunn, which won the award. (The rules have since been changed so an artist couldn’t have two album of the year nominees as a solitary lead artist.)

  • He lost an Emmy and a Grammy to the same popular singer.

    Sinatra’s first Emmy nod was for best male singer (1956). He lost to Perry Como. Two years later, he also lost again to the smooth, relaxed singer at the inaugural Grammy Awards. Como’s “Catch a Falling Star” beat Sinatra’s “Witchcraft” for best vocal performance – male.

  • He received three major honorary awards from the Recording Academy.

    He received a lifetime achievement award in 1965, a trustees award in 1979 and a Grammy Legend Award in 1995. The Grammys cut away to a commercial during his acceptance speech for the latter award. Sinatra was starting to slip and the Grammy producers and Sinatra’s own people didn’t want himself to embarrass himself on live television. Even so, the moment could have been handled more gracefully.

    Sinatra was only the second artist to receive a lifetime achievement award from the Academy, following Bing Crosby. The award was given to Sinatra “for his continuing dedication to the highest of musical standards, both as a performer and as a recording executive, and for his unswerving faith in and devotion to the beauty in music.”

    The reference to Sinatra as a recording executive pertains to his leadership of his own label, Reprise Records, after he left Capitol Records.

  • He received many other lifetime achievement awards.

    He received the Cecil B. DeMille Award at the Golden Globes in 1971, the Life Achievement Award from the Screen Actors Guild in 1972, the Pied Piper Award from ASCAP in 1979, was inducted into the National Broadcasters Hall of Fame in 1982, received the Kennedy Center Honors in 1983, a lifetime achievement award from the NAACP in 1987 and the American Music Award of Merit in 1998.

    In addition, he received the Presidential Medal of Freedomfrom President Reagan in 1985 and the Congressional Gold Medal posthumously in 1998.

    And he has three stars on theHollywood Walk of Fame — one each for motion pictures, recording and television.

  • Bette Midler won an Emmy for a TV special which parodied the title of a Sinatra special.

    Midler won her first Emmy in 1978 for Ol’ Red Hair Is Back. The title was a parody of the title of Sinatra’s 1973 special Ol’ Blue Eyes Is Back. In 1992, Midler serenaded Johnny Carson with “One for My Baby (And One More for the Road),” a song made famous by Sinatra, on the next-to-last episode of The Tonight Show Starring Johnny Carson. That brought Midler her second Emmy.

  • He sang songs that are forever identified with two of America’s greatest cities.

    Sixteen years before he recorded “Theme from New York, New York,” Sinatra sang “My Kind of Town,” a robust salute to Chicago, in the film Robin and the Seven Hoods. As noted above, the song received an Oscar nomination. Sinatra was named an honorary citizen of Chicago in 1975.

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