10. “Mack the Knife” by Bobby Darin
In 1959, Bobby Darin scored an unlikely international smash hit by updating “Mack the Knife,” a 1920s-era murder ballad from Bertolt Brecht’s Threepenny Opera. Unlike the pernicious moritat that provides the source material, Darin’s swinging upgrade is fun and refreshing. The song continuously changes key to ratchet up the tension, culminating in a glorious climax full of jazz and rock ‘n’ roll.
9. “Crying, Waiting, Hoping” by Buddy Holly
Featuring a folk rock arrangement foreshadowing The Byrds and early Beatles, “Crying, Waiting, Hoping” was one of Buddy Holly’s greatest technical accomplishments. Based on this posthumous single, it’s clear that Holly was well on his way toward reshaping the history of rock ‘n’ roll music. Instead, that trajectory was tragically altered on the day the music died, yet songs like this are a brilliant reminder of what could have been.
8. “I Loves You Porgy” by Nina Simone
Possessing a piano style to match Bill Evans and the most expressive contralto since Billie Holiday, Nina Simone’s show-stopping Porgy and Bess ballad is a masterclass in craft and emotion. The penultimate track on her 1959 debut LP, “I Loves You Porgy” seems to take more influence from Richard Wagner’s “Liebestod” rather than George Gershwin’s 1935 opera. Lush and extravagant, it’s a tune that encapsulates all of Simone’s greatest qualities.
7. “Misty” by Erroll Garner
While diminutive in stature, Erroll Garner’s piano playing was impossibly large, full of thunderous swells and vast reverberations. “Misty,” his most famous ballad, was inspired by a cross-country flight from San Francisco to Chicago. Through the haze of a thunderstorm, a rainbow peeked out, which prompted Garner to begin composing “Misty” on the spot, humming the framework of his greatest song. The passenger in the seat next to him summoned a flight attendant to make sure he was alright.
6. “You’re Gonna Miss Me” by Connie Francis
Soaring strings, doo-wop chord progressions and a soulful vocal performance all make Connie Francis’ “You’re Gonna Miss Me” the definitive 1950s pop song. Sometimes, a great song is a great song because, well, it’s just a great song. “You’re Gonna Miss Me” is catchy, seductive and the melodies are simply irresistible.
5. “My Ship” by Miles Davis
Miles Davis may be the most influential musician of the entire 20th century, which is why he appears more frequently than any other artist in this list. Choosing a favorite song from such a prolific artist is nearly an impossible task, but “My Ship” is my definitive choice. The song drifts by relaxed and unhurried, yet still carrying an aura of mystery and ambiguity. Just like with the rest of the Miles Ahead tracks, “My Ship” is a quiet masterpiece, one that requires patient attention and close concentration. It’s amazing that such a hushed sound could come from such a large ensemble.
4. “Get Thee Behind Me Satan” by Ella Fitzgerald
Not often in a popular song do you invoke Satan by name, yet Ella Fitzgerald’s rendition of this Irving Berlin tune stands out for this very reason. Featuring a lush string arrangement that contrasts the lyrical subject matter, “Get Thee Behind Me Satan” is eerie, sultry, haunting and mysterious — evil in all the right ways.
3. “Willow Weep for Me” by Frank Sinatra
Frank Sinatra Sings for Only the Lonely is, as the title describes, filled with solitude, seclusion and withdrawal. Even “Willow Weep for Me,” which features beautiful orchestrations and complex structural arrangements, has a desolate feeling of isolation. Nevertheless, Sinatra’s amazing vocal performance brings the song to vivid life. The greatest contrast of all is how effortlessly Sinatra is able to share his loneliness with the listener.
2. “Stairway to the Stars” by Serge Chaloff
“Stairway to the Stars” is a song completely at odds with its creator — a heavenly tune crafted by a hellish persona. Serge Chaloff was a brilliant baritone saxophonist who lived a chaotic life filled with drinking, drug abuse and dangerous excess. Yet “Stairway to the Stars” is an astonishing moment of clarity, an expressive and emotional interlude that floats in from another world. It’s a miracle that such a destructive personality could create what might be the single greatest jazz song ever made.
1. “Everyday” by Buddy Holly
When I first set out to compile this list, one thing was certain: “Everyday” by Buddy Holly would claim the number one spot. Everything about the song is perfect, from the celesta-tinged main melody to the deceptively mature lyrics. Nostalgic, hopeful, tender, melancholy, subdued and lovelorn, Holly encapsulates the dreams and desires of an entire era of American history in only two minutes and nine seconds.
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