Top 20

Top 20 Singer-Songwriters of All Time

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Wed, May 7, 2014 at 8:56 AM
click to enlarge Johnny Cash - COURTESY OF THE LABEL
  • Courtesy of the label
  • Johnny Cash
There's something about the singer-songwriter, the self-contained musical artist whose compositions succeed largely on the strength of his or her imagination. When determining our top 20, we considered both solo artists, and singers who were the primary songwriters for their bands. -Nicholas Pell 

  • Screencap from The Midnight Special performance
  • Gordon Lightfoot
20. Gordon Lightfoot
There are two kinds of people in this world: Gordon Lightfoot evangelists and people who've never actually bothered to listen to him. His champions include Bob Dylan, Vincent Gallo and the entire nation of Canada. Even his most recognizable hits, "Sundown" and "The Wreck of the Edmund Fitzgerald" run rife with darkness. "10 Degrees and Getting Colder," is a tale about what are perhaps the last minutes of a hitchhiking failed country singer. Quit the ironic snickering and head down to the local dollar bin - ten bucks will grab you most of his catalog. -Nicholas Pell

click to enlarge Dolly Parton - COURTESY OF THE ARTIST
  • Courtesy of the artist
  • Dolly Parton
19. Dolly Parton
All through the '80s, Dolly Parton was a boob joke. Then, in 1992, Whitney Houston belted out "I Will Always Love You," and the world was reminded that Dolly had written this epic end-of-an-era tune about Porter Wagoner, and that she had written thousands of songs and sung them with more blonde ambition than Madonna could ever dream of. And, Jack White? You will never achieve Dolly's level of Nashville swagger, no matter how hard you riff on "Jolene." -Cristina Black 

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click to enlarge Elliott Smith - COURTESY OF THE ARTIST
  • Courtesy of the artist
  • Elliott Smith
18. Elliott Smith
Good Will Hunting. American Beauty. The Royal Tenenbaums. Each film has at least one character struggling with depression. So it's probably no coincidence that each soundtrack features hauntingly beautiful music from the late Elliott Smith. An ever-evolving musician - compare the instrumentation on Roman Candle and Figure 8 - he was also capable of conveying gut-wrenching emotion without sounding disingenuous. His soft, plaintive voice and harrowing lyrics are perfect for whenever sorrow looms. -Max Bell

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