20. “Train Whistle Blues” by Jimmie Rodgers
Before Jimmie Rodgers invented country music, he worked on the railroads throughout Mississippi. Trains weren’t seen as a sign of escape; in fact, they symbolized the opposite. For Rodgers, a train was nothing more than another dead end. That’s why many of his best songs were lonely blues tunes inspired by his life as a brakeman. “Train Whistle Blues” builds on the mythos of the lonesome railroad by combining a rickety arrangement with Rodgers’ ghostly train-whistle yodeling.
19. “Devil Got My Woman” by Skip James
The gloomy, minor-key sound of Skip James’ guitar was quite unique in the world of Delta blues. Likewise, his classically-influenced fingerpicking style shared more in common with the Piedmont blues of the East Coast than his Mississippi contemporaries. “Devil Got My Woman” captures James at his best — a haunting spiritual that wallows without pretense.
18. “Lazy River” by Louis Armstrong
“Lazy River” opens with a memorable trumpet line. The music then pauses so Louis Armstrong can interject: “Yeah, Uh-huh, Sure, Uh-huh, Way down, Way down.” He then sings the first verse as if he were playing a syncopated solo. Pretty soon, he breaks out into a full-fledged scat. A second trumpet solo finishes the song with a rousing climax. By the end, there’s no doubt that “Lazy River” is the entire Armstrong experience, a seminal example of his groundbreaking artistry.
17. “Stormy Weather” by Ethel Waters
Ethel Waters debuted “Stormy Weather” at Harlem’s Cotton Club in 1933. Waters’ career as a jazz singer was just about to take off, while the Cotton Club’s reputation as America’s most influential jazz hub was waning. “Stormy Weather” remains the greatest landmark for both: a signature song for the genre’s first female star, and a historic moment for the venue which first gave the genre a home.
16. “Twilight on the Trail” by Bing Crosby
Bing Crosby was a pop master adept at all genres: swing, Christmas songs, Hawaiian music, etc. But he was often at his best when he set his sights on the American frontier. Crosby’s first solo album, the 1939 collection called Cowboy Songs, featured some of his most sincere renditions. For whatever reason, he always seemed at home in the West. The highlight is “Twilight on the Trail,” a dreamy ballad that was President Franklin D. Roosevelt’s all-time favorite tune.
15. “Hellhound on My Trail” by Robert Johnson
Robert Johnson’s acoustic guitar playing was the stuff of legend, and to this day he remains one of the instrument’s most talented performers. But that’s just one half of his artistry. His strangely soulful voice, which easily glides from the upper register down to low baritone and everywhere in between, changed the trajectory of 20th century pop. Johnson’s vocal versatility communicates a wide range of emotions in every song. It’s the perfect complement to his guitar, which provides an entire orchestra unto itself.
“Hellhound on My Trail” is a magnificent example of everything that made him the “King of the Delta Blues Singers.” He delivers a world of detail into every note and inflection, making for a masterpiece that always reveals something new.
14. “Strange Fruit” by Billie Holiday
Billie Holiday’s “Strange Fruit” was uncompromising when it was released in 1939, and it still holds that same revolutionary power over 80 years later. The mournful dirge ushered in the civil rights movement, but that’s not the sole reason for its success. Nobody could emote like Holiday, and her evocative vocal performance in “Strange Fruit” is heartfelt and profound. She means what she sings. More than anything, the song is haunting — a stark portrayal of racism in its evilest form.
13. “Over the Rainbow” by Judy Garland
Lyricist Yip Harburg was inspired to pen “Over the Rainbow” by a single idea (according to Wikipedia): “a ballad for a little girl who… was in trouble and… wanted to get away from… Kansas. A dry, arid, colorless place. She had never seen anything colorful in her life except the rainbow.” Composer Harold Arlen had a similar moment of clarity coming up with the song’s music while parked on the side of the road. And Judy Garland memorably brings it to life as Dorothy in The Wizard of Oz. Even when setting aside the film, “Over the Rainbow” is as perfect as pop songs get.
12. “Just One More Chance” by Bing Crosby
Bing Crosby’s voice was never better than in his 1931 hit song “Just One More Chance.” His voice is deep and full-bodied, yet still youthful and flexible. The crooning is confident and passionate. He expertly controls his pitch and timbre, lending a triumphant swagger to the apologetic lyric. Meanwhile, a plaintive string section backs his longing vocals, making for a song that is striking on all fronts.
11. “Love in Vain” by Robert Johnson
In “Love in Vain,” Robert Johnson relegates the guitar to the background. With the spare accompaniment, the elegiac lyric and vocal take center stage. The end result is the most tender tune to ever come from the Delta blues. Johnson breaks his heart over a lost lover, whom he cries out for by name toward the end. Never before had the blues been laid so bare. Prior to “Love in Vain,” pop songs were simply passed down from one performer to the next — Johnson was the first singer/songwriter to take things to a more personal level.
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