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 

Gordon Lightfoot; Credit: Canada Hall of Fame

Gordon Lightfoot; Credit: Canada Hall of Fame

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

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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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

Hank Williams; Credit: Courtesy of the label

Hank Williams; Credit: Courtesy of the label

17. Hank Williams
With apologies to Jimmie Rodgers, Hank Williams is country music, and not just because handlers followed him everywhere, keeping his drug addiction under wraps. His slim corpus represents some of the finest songwriting ever, genre be damned. Though mainstream country threw him under the bus, Hank continues to inspire today's traditionalists such as Whitey Morgan, Sturgill Simpson and Lydia Loveless. Hank taught us it takes a world of hurt to play country like it's meant to be played. -Nicholas Pell

David Bowie; Credit: Album cover art

David Bowie; Credit: Album cover art

16. David Bowie
It's hard to even know what to call David Bowie: Ziggy Stardust, The Thin White Duke, Aladdin Sane, The Man Who Sold The World, or (my personal favorite) Jareth the Goblin King. All of those characters were responsible for classic material, but perhaps the most groundbreaking of Bowie's identities was his sexual one. Openly bi-sexual, he successfully proselytized Mick Jagger into a love affair. Playboy playmate Bebe Buell claims the two often propositioned her to join them in orgies with “four gorgeous black women” or “four gorgeous black men.” Also, the fact that a British bloke wrote a song with as much plastic Americana soul “Young Americans” is a testament to Bowie's abilities. -Kai Flanders

15. Johnny Cash
Cash was the original country outlaw. If Elvis was the flashy extrovert of the 50s, Johnny Cash was the sullen brooder. As we know, he was never stuck in Folsom Prison and he never shot poor Delia down. You'd be forgiven for believing that he did, though, with his mournful vocals ringing over his slow-and-steady “boom-chicka-boom” sound. His later catalog holds up and his work with Rick Rubin is easily the latter's greatest contribution to music. Sorry, Beastie Boys and Slayer. -Nicholas Pell

14. Prince
If Prince had only written and produced “Little Red Corvette,” “When Doves Cry,” and “Purple Rain,” his legacy would still be secure. After signing to Warner Brothers at 17 (and recently re-entering the fold with them), The Purple One reshaped pop music in his image, and it looks more like him with every passing decade. -Molly Bergen

13. Stevie Wonder
Stevland Hardaway Judkins got signed as a singer-songwriter to Motown records – at age 11 – after performing his own song “Lonely Boy” to Ronnie White of the Miracles. Wonder started touring at 12 and co-wrote a lot of his hits, including “Uptight (Everything's Alright)” “I Was Made To Love Her” and “Signed, Sealed, Delivered I'm Yours.” Those were his teenage efforts, and you know the rest. He remains a fountain of songs, bringing joy to all who hear him. -Molly Bergen 

12. Van Morrison
Blues legend John Lee Hooker once said, “Van's a real blues man and he has the blues inside him. It doesn't matter whether he's white or Irish.” And no matter which genres Van Morrison commingles – folk, pop, jazz – the soulfulness and inherent pain of the blues remains in his voice. His imagistic lyrics are delivered with a Jocyean stream of consciousness, capable of rendering Belfast countryside celestial. The distinctive and deliberate lyrical repetition Morrison often employs deepens the listener's understanding of the music and themselves. -Max Bell

11. Willie Nelson
Willie Nelson's lovable iconoclasm was born of Depression-era Texas, his parents' whiskey-fueled wanderlust, and the moral rectitude of the grandmother who raised him. Across his long career – '60s jukebox naïveté, earnest '70s outlaw country (“You can't make a record if you ain't got nothin' to say”), singalong '80s chart toppers (“On the Road Again,” “Always on My Mind”), and even oddities like Countryman, his 2005 reggae foray – the strengths of Nelson's songwriting are constant: honesty, humor, and an unflinching subversive edge. -Theis Duelund 


Robert Johnson; Credit: Redferns

Robert Johnson; Credit: Redferns

10. Robert Johnson
Robert Johnson is the most important bluesman in history; Rimbaud, from the Mississippi Delta . A street corner myth; a supernatural strummer; the devil's prodigy – nobody knows for certain. He first recorded in 1936; he died a year later at 27. The cause, a mystery. Some say he was done repaying Satan for his talents. That's probably true. -Art Tavana  

See also: Top 20 Musicians of All Time, in Any Genre

9. Tom Waits
Before he was a raspy carnival barker, Tom Waits was a boozy barfly, a bargain bin Bukowski wielding a switchblade in a moth-eaten suit. His eclectic catalog includes Jackson Browne-style ballads, booze-soaked blues stompers and Beefheart worship. But one thing's certain: Waits crafted some of the best lowlife poetry this side of Buk, from “Well I bet she's still a virgin / But it's only 25 'til 9” to “but he ain't no good Samaritan / he'll make sure he's reimbursed / lot more than $29.00 and an alligator purse.” -Nicholas Pell

Joni Mitchell; Credit: Jack Robinson

Joni Mitchell; Credit: Jack Robinson

8. Joni Mitchell
Joni Mitchell is a crazy cat lady. Which is clearly the way to go, because maybe all that domestic quietude has contributed to her writing, performing and producing some of the most introspective records ever made. Hauntingly sweet and sad and sexy, her 1971 album Blue may as well be implemented into modern science as an actual psychological stage, a phase that every young adult must go through or risk emotional retardation. -Cristina Black

7. Lou Reed
Fueled by heroin and self-loathing, Lou Reed deglamorized rock 'n' roll. With Velvet Underground, he influenced more bands than the Beatles. Then in 19 75, he released Metal Machine Music. “I was trying to do the ultimate guitar solo,” said Reed, shortly before his death in 2013. MMM was over an hour of sharp feedback. He was a bullshitter (it was no guitar solo). But above all, Lou Reed 's words gave punk its first taste of street cred. -Art Tavana

Leonard Cohen; Credit:

Leonard Cohen; Credit:

6. Leonard Cohen
Advice: If you show up at someone's house for a romantic hang, and they are playing a Leonard Cohen record when you arrive, consider backing away slowly. Cohen is a consummate cry-to, and you will never, ever, know how the object of your affection feels. -Cristina Black

5. Townes Van Zandt
Like so many great singer-songwriters (see #1), Townes Van Zandt re-created himself through song. In truth, he was a Texas son of privilege whose desperate substance abuse struck him down in what could have been his prime. It's probably best to see his catalog as apart from himself, as it's often hard to see him in it, the way it's so easy with lesser artists. Regardless, it contains some of the most precisely-descriptive, emotionally upsetting, hilarious and heartwrenching songs put to record. -Ben Westhoff  

4. Bruce Springsteen
Springsteen is somehow considered too pop, or too polished for some of the most self-hating of music fans, and indeed albums like The River and Born in the U.S.A. contain not a note out of place – though that's the result of his (oft-obnoxious) perfectionism rather than any sort of corrosive record label influences. But why anyone would fault a guy who could write the perfect pop song, over and over – with increasingly emotional resonance – remains a mystery. His catalog up through the '90s is basically flawless, and with each work he found new ways to tell truth. We might never know what, exactly, propels Springsteen to play evangelistic three hour plus shows around the country into his advanced age; the best guess is a deeply-buried need to please every last one of us. Though perhaps not the best way for him to live, for it we can nonetheless thank the Lord. -Ben Westhoff

3. Neil Young
Though they've tried, none of the derivative songwriters troubadour-ing their way through his wake can capture the tousled genius of Neil Young. From his coke-nosed rockstar days to the wizened grey elder statesman he's become, the Canada-born Young has told the great American story with a sage's acumen. In his ongoing 50-year career, he's tried his hand and his voice at genres ranging from techno to grunge – always managing to expound on every shade and hue in the range of human emotions. –Paul T. Bradley

2. Paul Simon
Paul Simon spent the first part of his career living resentfully in the shadow of the edgier, artier Bob Dylan – he even released a nasty but pretty spot-on Dylan parody, “A Simple Desultory Philippic” in 1965. Since the folkie era, he's carved his own path, igniting world music with Graceland and enjoying a late-career renaissance with 2011's brilliant So Beautiful or So What. Whether on gentle folk ballads or rollicking Afro-pop, Simon's genius has always been for turning the prosaic into poetry: finding prophecies in graffiti on “The Sound of Silence,” evoking years of marriage in the lyric, “The bedroom breathes in clicks and clacks” on So Beautiful's “Love and Hard Times.” He's the Fitzgerald to Dylan's Faulkner, a master of economy and style with just enough edge of his own. -Andy Hermann

1. Bob Dylan
Discussing Bob Dylan without lapsing into cliché is near impossible: The great American songwriter; the man who introduced the Beatles to grass; the motorcycle-riding iconoclast. Uncomfortable with his own fame, he didn't want to be the voice of his generation. “I never wanted to be a prophet or savior,” he told Ed Bradley, “Elvis maybe.” But Elvis wasn't a songwriter like Dylan; nobody was, and while everyone has a favorite Dylan album, we've all been touched by him in the same way – as someone who can express the pain and complications of life on earth in a way we've felt. -Nicholas Pell

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