It's not an overstatement to say that Frank Sinatra is the voice of a generation. Arguably the most important American musical figure of the 20th century (save perhaps for Elvis Presley), Sinatra's legendary career lasted a golden 60 years. He took off in the 30s and 40s, defined the "sing era" of the 40s and 50s, and still attracted listeners despite the popularity of the rock era in the mid-50s and 60s. He's nothing short of classic.
Sinatra's death day recently passed (May 14). The iconic singer would be 106 years old if he were alive today. We've already done a Top 10 list of Sinatra's greatest love songs, so in celebration of his life and legacy this year, we're kicking it up a notch and counting down his Top 10 best songs of all time! We know – it's a difficult feat, but we're up for the challenge.
Practically every Sinatra song has enough gusto to make this list, but today we're picking the best of the best based on their commercial and critical success, lyrical content and music production, and of course, legacy. We hope some of your favorites make the cut. Without further ado, here are our picks!
10. "Love and Marriage"
One of the best wedding songs ever made! "Love and Marriage" feels grand, bouncy, and includes a plethora of cute, playful rhymes. While it's not the most modern song in Sinatra's discography (love and marriage don't neccessarily need to go together like a horse and carriage in the 21st century), it's still fun to sing along to.
"Love and Marriage" was first introduced by Frank Sinatra on an episode of the 1955 television series Producers' Showcase. Sinatra went on to record two versions of the song. The first was recorded for Capitol Records on August 15, 1955 and became a major chart hit, while the second version was recorded for the Reprise Records album A Man and His Music ten years later. The Capitol version was eventually used as the theme song for the 1987–97 Fox TV sitcom Married... with Children.
9. "I've Got the World On a String"
Originally written and composed by Ted Koehler and Harold Arlen for the 1932 Cotton Club Parade, this song has been covered by Michael Buble, Louis Armstrong, Ella Fitzgerald, Barry Manilow, Diana Krall, and more greats. "I've Got the World On a String" was released in 1953, and according to Genius, has been called “one of the most aggressively cheerful songs to come out of America’s most dismal decade.”
The arrangement was made by Nelson Riddle, a frequent collaborator of Sinatra's. Alan Livingston, who felt Sinatra needed a new sound that his previous arranger Axel Stordahl was unable to provide, cleverly introduced Riddle as a substitute conductor. Sinatra was unaware of who Riddle was before their first recording session, but the moment he heard Riddle's “I’ve Got the World on a String,” he knew he'd struck gold.
We think Riddle's arrangement perfectly captures the upbeat nature of the lyrics. And, Sinatra’s joyous interpretation of this song fits right into the groove, with his playful baritone voice adding an extra hopeful whimsy feel to this classic ditty.
8. "I've Got You Under My Skin"
This ballad from Ol' Blue Eyes feels like it comes from the heart. The tune was originally written by composer extraordinaire Cole Porter in 1936, and Sinatra made it more popular with this rendition in 1946.
Once again, Nelson Riddle handles the arrangement. (Behind every great singer, there's an even greater producer/arranger!) It's got a bit of his magic in its mix along with a jazzy flair. We love the swelling strings, Sinatra's lower notes, and the playful brass. This is a bop we included on our Sinatra love songs list, and we still believe it's one of the most romantic songs ever made.
7. "Strangers In the Night"
We think it's hilarious when an artist absolutely hates a song from their catalogue, only for the song to become a #1 hit. It happened to Kurt Cobain of Nirvana with "Smells Like Teen Spirit", and it happened to Frank Sinatra with "Strangers In the Night." Sinatra had nothing but bad things to say about this tune, calling it a "piece of sh--," and per Frank Sinatra by Jean-Pierre Hombach, the “worst f---ing song that I have ever heard.”
Even so, "Strangers In the Night" would become Sinatra's first #1 hit since 1955’s “Learning the Blues.” It was based on the song “Broken Guitar” by Avo Uvezian and rewritten by Bert Kaemphert with English lyrics by Charles Singleton and Eddie Snyder. It was also the title track for Sinatra’s most commercially successful album, Strangers in the Night, which earned him three Grammy Awards in 1967.
While Sinatra hated this tune, we love it for its beautiful orchestration, gracefulness, and romantic tones.
6. "Summer Wind"
"Summer Wind" can conjure up a lot of images for people thanks to its poetic lyrics. Perhaps it makes you think of golden sand on a beach, or a hot evening strolling down a bustling seaside town. With a combination of lively saxophones, slow and steady drumming, and Sinatra's building vocals, "Summer Wind" remains a beloved classic. No matter what season you listen to it in, it makes you excited for the warmer months.
This song, written by Heinz Meier, was originally released in Germany as "Der Sommerwind" with German language lyrics by Hans Bradtke. Johnny Mercer re-wrote the song in English with the same themes as the original, which talked of the changing seasons using the Southern European sirocco wind as a metaphor. Wayne Newton was the first American artist to record the song, with Bobby Vinton and Perry Como also recording a rendition before it got into Sinatra's hands. We think "Summer Wind" is one of Sinatra's most relaxing tunes.
5. "Luck Be a Lady"
Doing covers of Broadway showtunes was pretty common back in the 40s, 50s, and 60s. "Luck Be a Lady" is a song written by Frank Loesser in 1950 that's featured in the musical Guys and Dolls. Being from the musical, the song's lyrics tell a tale about a character from the show trying to win a dice game to win the girl of his dreams.
Frank Sinatra starred in the 1955 movie version of Guys and Dolls alongside Marlon Brando, Jean Simmons, and Vivian Blaine. While Brando sang this song in the movie, Sinatra later recorded his own version of "Luck Be a Lady" for the 1965 album My Kind of Broadway.
The orchestration and Sinatra's voice on this version of the song are lush and full of emotion. While "Luck Be a Lady" is a popular song in musical theatre, laypeople unfamiliar with the stage know this song as Sinatra's.
4. "Theme From New York, New York"
It's always a happy moment whenever you hear this song play after the New Year's Eve ball drops during Dick Clark's New Year's Rockin' Eve. This track, along with Jay-Z and Alicia Keys' "Empire State of Mind," is considered the unofficial anthem of New York City. Take a trip to the city, and we can promise you there's a good chance you'll hear a tourist's car blasting this jam out into the streets.
The song, composed by John Kander with lyrics by Fred Ebb, is originally from the 1977 Martin Scorsese film New York, New York. It was written for and performed in the film by the legendary Liza Minnelli. Frank Sinatra didn't touch it until he started performing it at concerts, particularly at Radio City Music Hall in October 1978. In 1979, Sinatra recorded "Theme from New York, New York" for his 1980 album Trilogy: Past Present Future.
It's a song still closely associated with him today, it's not hard to know why: the twisty melody is one of the most recognizable in history. "Theme From New York, New York" brings out the city's glitz, glamour, and hopefulness, and Sinatra's grand voice fits perfectly into that mix.
3. "Fly Me to the Moon"
Another song included on our Sinatra love songs list. "Fly Me to the Moon" is an undisputed classic. It's a popular standard song written by Bart Howard in 1954, but Sinatra's version is easily the best there's ever been.
"Fly Me to the Moon" was originally titled “In Other Words,” and was introduced by Felicia Sanders in cabarets. The song became known as its current title thanks to the song's first line, and after a few years, the publishers changed the title to "Fly Me to the Moon" officially.
With help from Count Basie, Frank Sinatra recorded this version of the song for his 1964 album It Might as Well Be Swing. This version was arranged by Quincy Jones, who changed the time signature from ¾ waltz-time to 4/4. It gives the song a looser, swing feel – which helps make it more memorable and flirtatious. This rendition fills our heart with song. In other words, we love it!
2. "That's Life"
This song's been popularized in recent years thanks to its use in the movies Joker, A Bronx Tale, and Casper. Outside of film work, "That's Life" is notable for its poignant commentary about life as an entertainer. For those trying to make it in the industry, this is an enduring theme song.
But more than that interpretation, "That's Life" communicates the inspiring message of not giving up despite ups and downs. The orchestration is cheerful yet paced, as if to say, "hey buddy, we know things have got you down right now, but there's no reason to worry!" We particularly love the wordplay with alliteration during each chorus, specifically the lines, "I've been a puppet, a pauper, a pirate, a poet, a pawn and a king / I've been up and down and over and out, and I know one thing."
"That's Life" was written by Dean Kay and Kelly Gordon and first recorded in 1963 by Marion Montgomery. After hearing a cover by O.C. Smith, Sinatra recorded his version in 1966, and named his subsequent album after the track. The song proved successful and reached No. 4 on the Billboard Hot 100 chart.
Following the success of Sinatra's version, it was recorded by many other artists, including Aretha Franklin, James Booker, Shirley Bassey, James Brown, Van Morrison, David Lee Roth, Michael Bolton, Michael Bublé, Russell Watson, Deana Martin, and Holt McCallany.
1. "My Way"
Although this song has a reputation for being the "universal anthem of a--holes everywhere" according to John Oliver, we still think "My Way" is moving enough, iconic enough, and just enough of a masterpiece to take the #1 spot on our list. This power ballad is nothing short of theatrical. It starts off slow and contemplative, but then explodes into a sea of pride and strength with a roaring orchestra behind Frank's belting. It all makes you think about memories, living life to the fullest, and finding strength in yourself.
Written by Paul Anka specifically for Frank Sinatra, it uses the chords of “Comme d'habitude” by French singer Claude François. Anka bought the rights for this song for only a dollar! “I flew out to Vegas where he was at Caesars," Anka said once, describing the moment he first played the song to Sinatra. "I played it to him. I knew that by the reaction he gave me he was going to do it. I’m in New York two months later. The phone rings, Mr. Sinatra on the phone. He says, ‘Kid! Listen to this.’ Took the phone, put it up to the speaker. I heard ‘My Way’ for the first time and I started crying."
The song spent 75 weeks on the U.K. Top 40 singles chart and was also successful in the U.S., peaking at #27 in May 1969. The track was a success for not only Sinatra, but also Elvis Presley and The Sex Pistols' Sid Vicious, who released their own renditions, too.
But despite all its major success, "My Way" was another song Sinatra hated. According to his daughter Tina, "He always thought that song was self-serving and self-indulgent. He didn’t like it. That song stuck and he couldn’t get it off his shoe." Even though "My Way" can be used as a tune of selfishness when it's in the wrong hands, we still believe it's a motivating ballad about living life to the fullest and owning the choices you make before your final curtain.
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Article Image: A black and white photo of the cover and CD of Frank Sinatra's "Best Of" album. (Kraft74 via Shutterstock.)