Saluting Sinatra’s Centennial With a Look Back at 5 Iconic Songs

On December 6, CBS will air “Sinatra 100 — An All-Star GRAMMY Concert" to celebrate the late icon's 100th birthday. We're getting the party started with a roundup of some of Ol' Blue Eyes' classic tunes.
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Frank Sinatra Photo

Music fans are celebrating the musical legacy and centennial of Frank Sinatra, who was born on December 12, 1915. Pop singer Frank Sinatra poses for a portrait in circa 1958 in Los Angeles, California. (Photo by Michael Ochs Archives/Getty Images)

Francis Albert Sinatra, also known as Ol' Blue Eyes, The Voice, The Padrone of Popular Song and the Sultan of Swoon, came into this world on December 12, 1915. Although he passed away on May 14, 1998, his legacy lives on and continues to inspire a wide variety of musicians. 

So the Recording Academy, AEG Ehrlich Ventures and CBS have decided to honor the nine-time GRAMMY winner by presenting Sinatra 100 — An All-Star GRAMMY Concert to celebrate the late icon's 100th birthday. The live concert will be taped tonight at the Wynn Las Vegas Encore Theatre and broadcast on CBS on Sunday from 9–11 p.m. ET/PT.

Performers announced for the tribute include a wide range of popular musicians and Grammy winners, including Tony Bennett, Alicia Keys, Lady Gaga, John Legend, Carrie Underwood, Seth MacFarlane, Trisha Yearwood, Harry Connick Jr., Garth Brooks and Usher, who will sing Sinatra's instantly recognizable songs that were originally orchestrated by renowned arrangers Don Costa, Gordon Jenkins, Quincy Jones and Nelson Riddle

The event plans to integrate their tribute performances of his classic songs with rare archival footage narrated by the Chairman of the Board himself. The set list was kept under wraps until the show, but it’s likely that a few of the following tunes will make the cut. So here’s a look at the stories behind some of the songs Sinatra made famous, from his very first hit to his last live performance.

“I'll Never Smile Again”

In 1940, Frank Sinatra (backed by vocalist The Pied Pipers) and Tommy Dorsey and His Orchestra scored their first No. 1 hit with this 1939 song written by young Canadian songwriter Ruth Lowe. The song also has the distinction of being the inaugural No. 1 hit on the very first Billboard magazine chart, which eventually became America's defining measure of commercial success in the music business: the Billboard Hot One Hundred. The recording remained at No. 1 for 12 weeks, from July 27 to October 12, 1940. The song was inducted into the Grammy Hall of Fame in 1982 and, upon her death, Sinatra nominated Lowe for an honorary Grammy Award.

“New York, New York” 

Start spreadin’ the news: Sinatra actually had two hits titled, "New York, New York." Leonard Bernstein, Adolph Green, and Betty Comden wrote the first one, which salutes the Big Apple as “a helluva town where the Bronx is up and the Battery’s down.” Sinatra sang it alongside his fellow sailors on shore leave, Gene Kelly and Jules Munshin, in the 1949 film, On the Town

Thirty years later, Sinatra cut "(Theme From) New York, New York," by John Kander and Fred Ebb. Originally sung by Liza Minnelli in Martin Scorsese's 1977 bomb New York, New York, Sinatra transformed it into his signature song and concert closer. He reportedly angered lyricist Ebb by adding the climactic phrase "A-number-one." In 1993, Sinatra recorded a new version of the song as a duet with Tony Bennett

“Fly Me to the Moon” 

Bart Howard wrote the popular, upbeat standard “Fly Me to the Moon” in 1954. Originally titled “In Other Words,” Felicia Sanders first introduced it to the chic New York Nightclub, The Blue Angel. After a few years, the publishers officially changed the title. It became a bona-fide hit after Peggy Lee sang it on The Ed Sullivan Show in October 1960. However, Sinatra recorded the best-known version on the album It Might as Well Be Swing (1964), accompanied by Count Basie. Quincy Jones, who handled the arrangement, changed the time signature from 3/4 waltz-time to 4/4 and gave it a looser, swing feel. 

“It Was a Very Good Year” 

In 1961, composer Ervin Drake penned "It Was A Very Good Year," which Sinatra winningly recorded in 1965 as though it had been written explicitly for him. In fact, it was Drake’s attempt at writing a folk song; indeed, one of the decade’s most famous folk groups, the Kingston Trio, cut the track first. By happenstance, Sinatra heard this version while driving in car in 1965. To celebrate his 50th birthday, he had decided to make an album about a man contemplating "The September Of His Years." Though the version he heard sounds nothing like a Sinatra song, Sinatra heard the possibilities within the wistful lyrics and his singing is beautifully framed by Gordon Jenkins' masterful arrangement.

“My Way” 

Rat Pack hanger-on Paul Anka wrote the lyrics to what is arguably the song that most people associate with Sinatra. While vacationing in France, Anka acquired the rights to the original 1967 song (then titled, “Comme d'habitude (As Usual)” from its French composer, Claude François. Anka didn’t do anything with it until Sinatra told him in 1969 that he was retiring from the music business. He demanded that Anka write something for his swan song. Anka complied, using the original melody but writing all-new lyrics in just one night. Anka has recounted: “I started typing: ‘And now, the end is near...’ and it wrote itself from there.” 

As a living legend, Sinatra’s own experiences gave him the moral authority to really sell the song, which is likely why it remains such a signature tune. Yet more than 100 different artists have also covered the song, and some, such as Dorothy Squires, Elvis Presley and the Sex Pistols, found much success with their versions. It also continues to regularly top karaoke charts around the world and is one of the most popular songs requested at funerals.

“The Best Is Yet To Come”

With music by Cy Coleman and lyrics by Carolyn Leigh, 1959’s “The Best is Yet To Come” was originally written for Tony Bennett. However, Frank Sinatra, accompanied by Count Basie, under the direction of Quincy Jones, recorded it on his 1964 album It Might As Well Be Swing, and made it popular. On February 25, 1995, Frank sang this song for a group of 1,200 people on the last night of the Frank Sinatra Desert Classic charity golf tournament in Palm Springs, California. It would be the last song Sinatra ever sang in public, and the words “The Best Is Yet to Come” are inscribed on his tombstone.