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Top 50 Greatest Singer-Songwriter Albums of All Time

Updated: Apr 4

(Pictured - John Prine 1973)

Bob Dylan, Joni Mitchell, Nick Drake, John Prine, Paul Simon, all artists covering differing styles of music yet they seemingly all have one thing in common, being able to uproot an emotional response from listeners through their medium of musical expression, that of the singer-songwriter. Singer-songwriters come from all sorts of backgrounds, but in a general sense to the sound as a say, “genre,” the singer-songwriter style comes from a folk-acoustic style of musical delivery. Alongside the musician and their voice generally being the focal point of the singer-songwriter style, the vulnerable artists tend to write their own music, or cover that of other singer-songwriters, with the backing band (if even present) acting mainly to support the artist, although there are occasional exceptions.

The singer-songwriter tradition has been around for most of the twentieth century but for our criteria today, we’re pretty much only looking at records post-1960 as the styles of music were just too different to compare. It’s hard enough to score Elliott Smith or Ryan Adams albums alongside Bob Dylan, let alone someone like Woody Guthrie or Pete Seeger. Pre-1960 singer-songwriter records just fall in a category of their own. Most country albums have also been excluded from our criteria as they fall in a more narrowly defined category, although folk artists who dipped over into country like Steve Goodman or John Prine are eligible. Alongside that, all the albums selected center around the singer-songwriter and not the ensemble behind that - That is why Nebraska by Springsteen is eligible, but Born to Run is not. Lastly, for once, most of the albums on our list today are that of American and Canadian artists. Not to take anything away from the Brits, but the singer-songwriter style just caught more steam in the US. To our British readers, as you know, you guys dominate our rock rankings (which although certain albums may appear on both lists, are judged differently based on the specific context), and for good reason. Below are our picks for the greatest singer-songwriter albums of all time.

1. Blonde on Blonde - Bob Dylan

Bob Dylan had an unparalleled ability to connect with listeners on a level so deep and thought-provoking. Dylan’s cryptic lyrics release different emotions in different listeners, with his true lyrical meanings often hiding beneath his words. Nevertheless, Dylan captured the attention of a generation daring to simply ask “why?” So much of what Bob Dylan did in the 1960s and 1970s can be discussed within the conversation of“perfect,” with his 1966 double album Blonde on Blonde being his most "perfect" LP. Dylan showcased a hypnotizing musical delivery that no one was quite able to figure out or replicate. By our standards, Blonde on Blonde is Dylan’s masterpiece and the finest LP by a singer-songwriter, as well as one of the ten greatest rock records of all time. Dylan's unique mix of folk, rock, and blues was exceptional, not in a way that makes one's jaw drop, but in a way that makes you subtly shake your head and smirk. The Brits may have had the Beatles, but we in the States had Dylan.

2. John Prine - John Prine

In the ‘70s, Chicago saw a folk-revival explosion, cementing it as the place to be for folksy, singer-songwriters. The catch is though at the time, the notoriety surrounding the scene was mainly localized, and the legacy and importance of the scene would not get the respect it deserved for quite some time. At the forefront of musicians who did not get the initial respect they deserved was John Prine. Prine’s first album, is a shockingly strong debut, with Prine singing a type of folk-forward country that would take a bit of time for people to digest. Surely enough for John Prine though, it would later become one of the most remembered and covered collection of songs for generations of American musicians to come ranging from fellow Chicago icon Steve Goodman to Bonnie Raitt, Jimmy Buffett, John Denver, Sturgill Simpson and even the Everly Brothers. Essentially every song on this record is frequently covered to this day as its larger than life legacy continues to grow. The majority of the record is made up of sad tales, singing on behalf of down on their luck protagonists, while Prine sprinkles in humor throughout the way. Hello In There tells a heartbreaking tale of lonesome aging and becoming detached from yourself while Donald and Lydia conveys a sad narrative about feeling out of place, until Prine professes the song is about masturbating, unleashing a surprising level of unexpected humor.

3. Grace - Jeff Buckley

The son of esteemed American songwriter Tim Buckley, Jeff Buckley amassed himself an equally impressive legacy. Both Buckleys had their time on earth tragically cut short, with Tim dying of an overdose at the age of 28 and Jeff drowning at the age of 30. Jeff Buckley's lone studio album Grace attracted a massive amount of initial underground attention and broader mainstream attention retrospectively as the treasured record became exposed to more and more listeners. Grace was a genre-bending album, harnessing elements of smoke-filled jazz clubs while also holding Dylan levels of folksy, cryptic lyrics and '90s-esque, college radio-friendly alternative rock. Songs like Lover, You Should've Come Over do all three at the same time, with Buckley unleashing his prowess as a vocalist with an incredibly impressive range. Lover, You Should've Come Over  remains an incredibly powerful love song, wrestling with harsh realities of aging and regret. Just before the powerful love song, Buckley crafted perhaps the most recognizable version of Leonard Cohen’s iconic track Hallelujah. Grace is one of those records that may have flown under the radar for many upon release in 1994, but by the end of the decade, it was pretty clear it was one of the best American records of the ‘90s.

4. Warren Zevon - Warren Zevon

In the 1970s, Warren Zevon was one of the most well-respected musicians amongst musicians in Los Angeles, although his mainstream success was rather limited. Zevon roomed with Lindsey Buckingham and Stevie Nicks, who had just teamed up with Mick Fleetwood and the McVies to form yet another version of Fleetwood Mac, alongside befriending Jackson Browne, who produced this album. Zevon’s substance abuse issues, primarily with alcohol, are well documented throughout the '70s as he struggled with an undiagnosed case of OCD. Alongside masking his ailment, drugs provided Zevon, who was otherwise an introvert, with a serious sense of swelling confidence, which equally resulted in some of his finest songs. Zevon's substance issues allowed him to convey an authentic sense of desperation heard in songs like Carmelita and Poor Poor Pitiful Me. Zevon was also able to capture an unsuspecting beauty through expressing the more deplorable, underbelly of LA, a side unexposed to East Coasters, with a mystic, sunshine-laced, smiley depiction of the west coast City of Angels. Desperados Under the Eaves remains one of the most beautiful songs of the decade, as he brings the band up for that song's powerful outro, a reprise of Zevon’s piano lick that starts the album. Warren Zevon remains one of the most underrated musicians of the ‘70s, still being known by too few.

5. Horses - Patti Smith

In 1975, Patti Smith was on the cutting edge of the American punk rock scene. The New York punk scene was raw, taboo and energetic, attracting more and more people intrigued by the new sound of groups like The Ramones, who had yet to release an album but were nevertheless gaining localized attention from club shows. Upon the release of Horses in 1975, Patti Smith beat The Ramones to the punch, with their debut not coming until six months after Horses. Patti mixed singer-songwriter ideals with proto-punk passion to create a shockingly memorable debut. Produced by John Cale of The Velvet Underground, the record had a taste of the avant-garde nature of Cale’s band while being immediately more accessible than their niche, but deeply respected releases. Patti Smith proved herself dramatically ahead of her time on her debut album, mixing simplistic rock formats with authentically chaos-riddled lyrics, notably building on Gloria, one of Van Morrison’s finest creations. Smith’s songwriting ability was legendary just as much as her delivery, creating one of the most important records of the decade, especially on the American front.

6. Moondance - Van Morrison

Speaking of Van Morrison, the Northern Irish singer-songwriter’s third studio album has since become his most widely remembered, although it was his sophomore release Astral Weeks that has received the most critical praise. On Moondance, Van Morrison’s jazzy, blue-eyed soul approach to songwriting produced one of the most sonically pleasing records of the era. On Moondance, Morrison acted just as much a bandleader as a singer-songwriter. He entered the studio with song structures written down, but most of the lyrics and inner workings of the songs were yet to be developed. Through his time in the studio, Morrison crafted the ten unique tunes as he went, coming up with some of his most memorable tracks like And it Stoned Me, Into the Mystic, Glad Tidings, and of course, the jazzy album-titled track. Although Morrison backed himself with notable instrumentation, it was still Van at the forefront, the sole writer and focal point of all ten tracks. Van’s Celtic roots were on display expertly on Moondance, with that natural, Irish knack for catchy, flowing melodies, complementing his poetic lyrics. The album attracted wide attention from all walks of life, including old school, God-fearing American families alongside hippies and run-of-the-mill, average young Americans and Brits.

7. Either/Or - Elliott Smith

In the late ‘90s, Elliott Smith was the premiere indie darling of the United States, towing the line perfectly between folk, lo-fi and Americana, often acting as the sole musician in his tracks. On his third release Either/Or, he was indeed the sole instrumentalist and vocalist. Already having released two deeply praised, yet largely underground albums in the mid-‘90s, Either/Or, was the climax of the first three records, and according to many, the musician's creative peak. Either/Or, matches the precedent of the deep-thinking, mellow singer-songwriter. It’s now known the darkness of his lyrics and his guitar playing were by no means a facade but was genuinely the byproduct of a sad soul, struggling to find happiness. Perhaps, the largest reason Either/Or, connected with so many on such a deep level was just that simple fact, that it was not by any means for show but was just Smith’s growing cry for help. Between the Bars and Angeles are two iconic tracks in the sad boi, indie singer-songwriter style, amongst two of the most remembered indie recordings of the ‘90s. Although the true inner workings of Smith’s mind will remain unknown, he was burdened with public mental health issues, treated through drugs and alcohol which too-often have tragic endings, as did in Elliott's case.

8. Harvest - Neil Young

Few singer-songwriters have amassed such a respected legacy as Neil Young, having found success with Buffalo Springfield and Crosby, Stills, Nash & Young before his even more impressive solo career. Outspoken for his often controversial, grandstanding positions on social issues, Young has been portrayed both as a longstanding proponent of positive social change and simply an individual who has put himself on a pedestal, deeming himself worthy to speak down to those with differing ideals. Wherever the truth may lay, Neil Young is a brilliant musician and one of the finest songwriters of the twentieth century. Sitting atop a long list of musical achievements for Neil Young is his fourth studio album, Harvest. The star-child track of the record Heart of Gold is perhaps Young's finest composition released throughout his impressive career, sounding somewhat akin to a powerful, yet somber campfire tune, with a band added as an enticing afterthought. Neil Young’s exposed vocals, alongside his mellow harmonica, created one beautiful sonic aura, sifting through a cold, night sky. The traditional singer-songwriters' ideals, espoused in Heart of Gold and Old Man, contrast brilliantly with the louder, more expansive instrumental sections showcasing the band behind him, notably the closing track Words (Between the Lines of Age).

9. Pink Moon - Nick Drake

Initially receiving mixed responses from both listeners and critics, Nick Drake’s third and final studio album did not sell very well during his lifetime, with its stripped-back sound being relatively uninteresting for many Brits at the time. Pink Moon did not really receive too much attention until the coming decades, and by the time the rereleases began coming out in the ‘90s, its brilliance had been uncovered. In a similar vein to Elliott Smith, Nick Drake’s dark and somber lyrical matter was not a facade but was just Nick honestly expressing himself. It’s been said that by the release of Pink Moon, Nick Drake’s aspirations for mainstream success had been dissolved, essentially leaving him with no one left to impress, meaning now might be a good time to be as authentic as possible. In listening to the record, that would sure seem true with it being void of any grandiose musical ideas, and instead made up of just what he felt and what he wanted to sing. Drake’s legacy has made a substantial impact on the indie/folk singer-songwriter sound, which sadly hit its stride long after Nick Drake’s 1974 death. All in all, Nick Drake was simply a man ahead of his time, who released three records the world was not quite ready for.

10. Blood on the Tracks - Bob Dylan

Following the end of the ‘60s, Bob Dylan continued to make his presence known through the ‘70s with his fifteenth studio album Blood on the Tracks quickly becoming a fan favorite among Dylan fans. By the release of Blood on the Tracks, the Bob Dylan sound had evolved through electrification on and off again, with Dylan’s folk hero persona still taking precedence over any band backing him. On that note, Blood on the Tracks again exposes a more stripped-down side of Bob Dylan, with much of the instrumentation, excluding the drums, coming from Dylan himself. The stripped-down, or at the very least Dylan-centered instrumental sounds, take nothing away from the sheer abrasiveness heard throughout the record, notably on Idiot Wind, exposing some of Dylan’s most angst-filled lyrics of the ‘70s. Following Idiot Wind, You’re Gonna Make Me Lonesome When You Go, and Shelter From the Storm later on the record, echo the stripped-down sound of Dylan’s first few albums very well, sounding like some form of evolved, pre-electrified early ‘60s sound. Perhaps more than anything, Blood on the Tracks professed that although rock was rapidly evolving and changing, Bob Dylan still had the creative might to successfully pursue his own direction, and that people still deeply cared.

11. Blue - Joni Mitchell

12. Illinois - Sufjan Stevens

13. Imagine - John Lennon

14. Paul Simon - Paul Simon

15. Songs of Leonard Cohen - Leonard Cohen

16. No Other - Gene Clark

17. Highway 61 Revisited - Bob Dylan

18. Excitable Boy - Warren Zevon

19. After the Gold Rush - Neil Young

20. Astral Weeks - Van Morrison

21. Sweet Revenge - John Prine

22. Sail Away - Randy Newman

23. Paris 1919 - John Cale

24. Tapestry - Carole King

25. Rain Dogs - Tom Waits

26. To Bring You My Love - PJ Harvey

27. Tracy Chapman - Tracy Chapman

28. Nilsson Schmilsson - Harry Nilsson

29. Nebraska - Bruce Springsteen

30. Scott 4 - Scott Walker

31. You Don't Mess Around With Jim - Jim Croce

32. Transformer - Lou Reed

33. Ys - Joanna Newsom

34. Hejira - Joni Mitchell

35. All Things Must Pass - George Harrison

36 Heartbreaker - Ryan Adams

37. Starsailor - Tim Buckley

38. Jessie's Jig & Other Favorites - Steve Goodman

39. Five Leaves Left - Nick Drake

40. A1A - Jimmy Buffett

41. Tea for the Tillerman - Cat Stevens

42. Norman Fucking Rockwell! - Lana Del Rey

43. Car Wheels on a Gravel Road - Lucinda Williams

44. On the Beach - Neil Young

45. XO - Elliott Smith

46. Sailing to Philadelphia - Mark Knopfler

47. Exile in Guyville - Liz Phair

48. Sweet Baby James - James Taylor

49. Punisher - Phoebe Bridgers

50. Guitar Town - Steve Earle

25 Honorable Mentions (Unranked)


The Hissing of Summer Lawns - Joni Mitchell

Good Old Boys - Randy Newman

I See a Darkness - Bonnie "Prince" Billy

Late For the Sky - Jackson Browne

Little Earthquakes - Tori Amos

Moon Pix - Cat Power

Gold - Ryan Adams

There Goes Rhymin' Simon - Paul Simon

Bruised Orange - John Prine

Living and Dying in 3/4 Time - Jimmy Buffett

Year of the Cat - Al Stewart

Eli & the Thirteenth Confession - Laura Nyro

Sundown - Gordon Lightfoot

The Way It Is - Bruce Hornsby & the Range

I'm Goin Down - Kurt Vile

Tim Hardin 2 - Tim Hardin

Harlan County - Jim Ford

The Freewheelin' Bob Dylan - Bob Dylan

Everybody Knows This is Nowhere - Neil Young (With Crazy Horse)

The Milk-Eyed Mender - Joanna Newsom

Somebody Else's Troubles - Steve Goodman

American Gothic - David Ackles

Saint Dominic's Preview - Van Morrison

Bringing It All Back Home - Bob Dylan

Stormcock - Roy Harper


2000's alternative & indie rock playlist cover 2.JPEG
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