The 100 Greatest Singer-Songwriter Albums of All Time
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Even though this list tries to be definitive, there can’t truly be a “greatest singer-songwriter album.” The genre itself resists that kind of certainty. What matters in singer-songwriter music is not consensus, but connection: the feeling that a song was written to reach someone, even to reach you specifically. That’s the connection we wanted to capture with this list.
We approached that idea from multiple directions at once. We asked a group of artists and writers to each submit a small set of albums that influenced them and their songwriting. It wasn’t always about the “best” records, but the ones that stayed with them. The albums that changed their perspective, or simply refused to leave their lives once they arrived. You can see the lists and commentary of every artist here.
It wasn't just artists though, we wanted to hear from you, the readers. We asked our readers for their top 3 singer-songwriter albums, as the people too are important in deciding this list. The genre has always been about the people, so there's no way to make this without them.
From those submissions, a larger picture slowly emerged. Some choices were expected, others deeply personal, and many existed in tension with one another. That tension is the point. A singer-songwriter list is never final; it’s a book written across decades, borders, and languages. This list is not an attempt to close that book, but to read it as clearly as possible.
What follows is a hundred albums that, together, show a shared language: the language of the singer-songwriter.
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The Mysterious Production of Eggs
Andrew Bird
100

White Light
Gene Clark
99

Walkin' My Cat Named Dog
Norma Tanega
98

Fairytale
Donovan
97

Count Bateman
Frog
96

Emitt Rhodes
Emitt Rhodes
95

Once I Was an Eagle
Laura Marling
94

I, Jonathan
Jonathan Richman
93

Cold Fact
Rodriguez
92

Old No. 1
Guy Clark
91

Heart Food
Judee Sill
90
"Judee Sill is getting some much deserved attention right now (though I haven't watched the new doc yet), and this record is an example of some of her crystalline songwriting. The arrangements are always there to real you in, but always letting the lyrics take the spotlight." - Abbey Blackwell

Here Comes Rhyming Simon
Paul Simon
89
"A master songwriter, but then all of these are. As with the other records here I could equally have selected several other of his albums. This one makes the cut because it has the incredible ‘American Tune’ with a lyric that has embedded itself into my mind: “And I dreamed I was dying / I dreamed that my soul rose unexpectedly / And looking back down at me / Smiled reassuringly.”" - Ian Paul Sharp

De todas las flores
Natalia Lafourcade
88

Soviet Kitsch
Regina Spektor
87

Diamonds & Rust
Joan Baez
86

Just Another Diamond Day
Vashti Bunyan
85

27 Demos
Margo Guryan
84
Favorite of: Rachel Love

Hi, How Are You: The Unfinished Album
Daniel Johnston
83

In My Own Time
Karen Dalton
82

I Got A Name
Jim Croce
81

Album III
Loudon Wainwright III
80

The Milk-eyed Mender
Joanna Newsom
79

Paul Simon
Paul Simon
78

Transa
Caetano Veloso
77

Warren Zevon
Warren Zevon
76

Tim Hardin 1
Tim Hardin
75

Moon Pix
Cat Power
74

Construcao
Chico Buarque
73

Parallelograms
Linda Perhacs
72
"One of my favorite albums of all time. I love this album because it takes you to so many different places. Sometimes stripped down, sometimes downright trippy, she is not trying to fit into some traditional mold. It's new and exciting every time I listen to it. Every time I drive through Chimacum on the Washington peninsula I put it on, and it pairs so perfectly." - Abbey Blackwell

Gilberto Gil
Gilberto Gil
71

Tracy Chapman
Tracy Chapman
70

Car Wheels on a Gravel Road
Lucinda Williams
69
"A monumental statement for a peerless artist. Cyclical family trauma. Survivor’s remorse. Complicated love. Lucinda tackles subjects other artists wouldn’t dare touch with the lyrical economy of a Farside cartoon. I don’t think I’ve ever heard a song tackle the shared disappointment of a relationship falling apart like these lines from “Metal Firecracker”:
All I Ask
Is don’t tell anybody the secrets
I told you
" - Pat King (of Labrador)

O
Damien Rice
68
"Mad Honesty, fragile depth, intense mundane love, 100% human." - Lau Noah

Sometimes I Wish We Were an Eagle
Bill Callahan
67

Our Mother In The Mountain
Townes Van Zandt
66

Punisher
Phoebe Bridgers
65

On The Beach
Neil Young
64

Colour Green
Sibylle Baier
63

Five Leaves Left
Nick Drake
62

Bone Machine
Tom Waits
61

U.F.O.
Jim Sullivan
60

Songs From Suicide Bridge
David Kauffman & Eric Caboor
59

Late for the Sky
Jackson Browne
58

Eli and the Thirteenth Confession
Laura Nyro
57

Darkness on the Edge of Town
Bruce Springsteen
56

Titanic Rising
Weyes Blood
55

Jackson C. Frank
Jackson C. Frank
54

Closing Time
Tom Waits
53
"A perfect movie. The pace, the surrender into the darkness of life, saved time and time again by his ability to create light out of nowhere. A masterpiece." - Lau Noah
" It’s a live album. Perfect storytelling. A perfect drinking companion. Elegant and lonely." - Orange Animal

No Other
Gene Clark
52
"This is an album that continues to fascinate me every time I put it on. A sober psychedelic experience filled with equal parts wisdom and poetry. The instrumentation is volcanic in its presentation with Gene’s voice and perspective chiseling its way into your soul. I’ve yet to hear a record that comes close to matching this record’s balance of country, gospel, and cosmic funk. It’s the direction that alt-country should have taken instead of the near-constant Gram Parsons clones of the last 50 or so years. " - Pat King (of Labrador)

Bryter Layter
Nick Drake
51

Desire
Bob Dylan
50

Scott 4
Scott Engel
49

Happy/Sad
Tim Buckley
48

Figure 8
Elliott Smith
47

Solid Air
John Martyn
46

Rickie Lee Jones
Rickie Lee Jones
45

Sail Away
Randy Newman
44

The Hissing of Summer Lawns
Joni Mitchell
43

After The Goldrush
Neil Young
42
"After The Gold Rush is Neil young free from expectations. If Harvest is him at his most Laurel Canyon folk-country and Everybody Know This is Nowhere is him writing the Crazy Horse handbook, this record is Neil at his most skeletal and personal. He would become more cynical—listen to On The Beach—but no other album gives you a picture of Shakey at his most bright eyed and threadbare. " - Pat King (of Labrador)

XO
Elliott Smith
41

John Prine
John Prine
40
"No other album in my lifetime has been as important as this album. Furthermore, no other album has spoken to the cancerous qualities the American dream had had on its citizens. Who knew a 24 year old postman from Illinois could predict the cyclical rage of the working class seeing their sons die in pointless wars, succumb to addiction as a coping mechanism, their small town pride diminished by capitalist greed, or the elderly get left behind amidst a world that is moving too fast? There is no wasted breath on this record and time has rightfully placed him where he belongs: next to giants of the craft such as Bob Dylan, Hank Williams, and Kurt Vonnegut Jr. " - Pat King (of Labrador)

Songs of Love and Hate
Leonard Cohen
39

Illinois
Sufjan Stevens
38

Françoise Hardy (Tous Les Garçons Et Les Filles)
Françoise Hardy
37

Court and Spark
Joni Mitchell
36

Moondance
Van Morrison
35

Tea For the Tillerman
Cat Stevens
34
"This is such a classic and I have heard this album soooo many times. From the opening track of "Where Do The Children Play?" which become more relevant by the day, through "Hard-Headed Woman" and "Sad Lisa" which both sound and feel so real every time I hear it, to "Father And Son" which strikes a chord whether you are a parent or a kid or both…simply worth playing on repeat for a while." - JoeJoe S

How Sad, How Lovely
Connie Converse
33

Idler Wheel
Fiona Apple
32

Songs
Adrianne Lenker
31

I'm Wide Awake, It's Morning
Bright Eyes
30
"This album is burned into my DNA. I listened to it so much when I first discovered it. I didn't know which ones were the “hits” until later, and I'm incredibly thankful for that. You know how sometimes on an album, when the hit comes up, it sorta takes you out of it? I'm always bothered by that, and thankfully this album is all one thing in my mind. Perhaps that is the reason why it bit so deeply into my soul." - Eric Stevenson (of Pocket Vinyl)

John Lennon/Plastic Ono Band
John Lennon/Yoko Ono
29
“My favorite Lennon album changes, but this has “Working Class Hero" which is one of my favorite songs” - Jonathan Root

Judee Sill
Judee Sill
28

You Don't Mess Around with Jim
Jim Croce
27
"I love Jim Croce and everything he does, but this record is such a perfect example of his lyric genius and earworm melodies. " - Abbey Blackwell

Bridge over Troubled Water
Simon and Garfunkel
26

Crying, Laughing, Loving, Lying
Labi Siffre
25
Crying, Laughing, Loving, Lying is an intricate mix of singer-songwriter and soul which brings forward the impressively awkward yet comforting quality of Labi Siffre’s voice and words. There’s something about him that simply makes you feel close. That connection along with the simple but effective guitarwork brings the album together in a wonderful way. - WAX

New York Tendaberry
Laura Nyro
24
New York Tendaberry feels less like an album and more like Laura Nyro unraveling in real time. The songwriting constantly shifts between beautiful and overwhelming without warning. Her voice is theatrical in a way that almost shouldn’t work, but it gives the album this impossible emotional intensity that completely consumes everything around it. - WAX

The Freewheelin' Bob Dylan
Bob Dylan
23
The Freewheelin’ Bob Dylan feels like the moment folk music stopped being preserved and started being weaponized. Dylan sounds young, scrappy, and completely unconcerned with polish. His voice can feel almost confrontational, but the songwriting is undeniable. Even the quieter moments carry this sense that music itself was actively changing around him. If any album can claim to be the start of the singer-songwriter genre, this one is it. - WAX
"My fav Dylan album changes day to day; hard to pick one, but today it’s this one" - Jonathan Root

Townes Van Zandt
Townes Van Zandt
22
Townes Van Zandt feels like isolation turned into music. There’s country here, but stripped of any grandiosity or charm. He sounds distant from everything around him, and that distance becomes the emotional core of the album. His voice is awkward, fragile, and deeply human in a way that’s hard to replicate. - WAX

When The Pawn...
Fiona Apple
21
When the Pawn… feels like Fiona Apple constantly pacing around the room while the album forms around her. The piano is jazzy but tense, like it could fall apart at any second. Fiona herself is the centerpiece though. She sounds bitter, exhausted, seductive, and completely self-aware all at once. It’s messy in a way that feels intentional. - WAX

All Things Must Pass
George Harrison
20
All Things Must Pass feels like George Harrison finally exhaling. For years he was stuck behind Lennon and McCartney, two of the biggest personalities music has ever seen, and then suddenly he drops a triple album overflowing with some of the best songwriting of the era. There’s something deeply spiritual about the album, but not in a preachy way. It feels more like acceptance. Harrison sounds relieved, exhausted, hopeful, and bitter all at once. The production can get overwhelmingly huge at times, that Phil Spector wall of sound almost swallowing the songs whole, but the songwriting is strong enough to survive it. Even at its longest, the album never stops feeling personal. - WAX
Favorite of:
Jonathan Root

Sweet Baby James
James Taylor
19
Sweet Baby James feels like the moment singer-songwriter music stopped trying too hard and simply embraced honesty. James Taylor isn’t a huge personality in the way Dylan or Cohen are, but that’s exactly why this album works. There’s a warmth to it that feels completely natural. The acoustic guitars, soft strings, and relaxed pacing make the whole album feel like late night conversation. Even when the songs get sad, they never become overwhelming. Taylor’s voice has this calm weariness to it that makes “Fire and Rain” hit especially hard. The album can drift into itself at points, but honestly that haze is part of the appeal. It’s comforting music without losing its emotional weight. - WAX

The Stranger
Billy Joel
18
The Stranger feels like the sound of a city staying awake long after midnight. This album is filled with piano ballads, barroom rock songs, and quiet confessions that make New York feel less like a place and more like a state of mind (even if that song isn’t on this album). Billy Joel has a warmth that makes the whole vibe instantly inviting. He writes with a conversational honesty that makes even his biggest hooks feel personal. Every song sounds lively, like stories traded across a dimly lit pool table. It’s a sharp, melodic, and uniquely genuine album about the parts of ourselves we try to keep hidden. - WAX

Nebraska
Bruce Springsteen
17
Nebraska feels like driving through empty highways with nothing but static on the radio and bad thoughts for company. Springsteen strips away his classic heartland rock grandeur and leaves behind bare acoustic guitars, harmonicas, and tape hiss that gives the album a ghostly quality. The songs are filled with killers, drifters, and people crushed under the weight of the American dream, but Springsteen never turns them into caricatures. He writes them with a quiet empathy that makes their lives feel lived. Even the silences on the record feel heavy. It’s a bleak and intimate album that finds terror in the ordinary despairs of life. - WAX
"To be honest, I do not like all of the songs on this album equally but it is definitely an album that I can listen to on repeat when I am in a melancholic mood. The lyrics are razor-sharp, the tunes pulse with melancholy and Springsteen's deliveries are a masterpiece of "less is more". I can just see him and hear him creating these songs while strumming on his guitar." - JoeJoe S

Harvest
Neil Young
16
Harvest feels like the countryside fading into the background of a painting. Neil Young strips the polish back, building the album around gentle acoustic guitars, weary melodies, and a voice that sounds cracked by experience. The record sways back and forth between homely warmth and quiet loneliness, capturing the uneasy space between comfort and being alone. Young’s songwriting is simple, but somehow manages to craft lines like a polished countertop with cracks. Even at its softest, there’s a sense that something is falling apart beneath the surface. It’s a humble, aching, and reflective record that turns fragility into one of its greatest strengths. - WAX

Rain Dogs
Tom Waits
15
Rain Dogs feels like a city in the middle of the night rotting in style. Tom Waits abandons almost every conventional instinct of the singer-songwriter genre to build a world out of junkyard percussion, broken pianos, and smoky cabaret melodies. The album stumbles through alleyways filled with drifters, thieves, and forgotten romantics, turning urban decay into his own strange mythos. Waits’ voice is impossibly rough, more growled than sung, but it gives the stories an undeniable authenticity. Beneath the bizarre instrumentation and theatrical chaos is a record about isolation and survival. It’s ugly, soulful, and alive in a way few albums ever manage to be. - WAX

Graceland
Paul Simon
14
Graceland is the sound of a songwriter revitalizing his craft by looking outward. Paul Simon moves away from the neuroses of New York to find a vibrant, percussive energy in South African mbaqanga music. The album is defined by its rhythmic complexity, where fretless bass lines and accordion flourishes create a shimmering, polyrhythmic backdrop. It’s an unlikely collision of world music and Western pop that never feels forced. Simon’s lyrics are surreal and scattered, capturing the disorientation of middle age and fame. It proves that the genre can be global and expansive without losing the personal intimacy that defines it. - WAX

Just As I Am
Bill Withers
13
Just as I Am is a masterclass in the power of simplicity. Bill Withers arrived as a fully formed artist, stripping away the usual polish of soul music to find something tactile and human. The production is lean, centered around a steady acoustic guitar and a voice that feels like kitchen-table perfection. He doesn't rely on showing off his vocals, but rather on the truth of his delivery. The songs treat everyday struggles as monumental, because to the people they affect, they are. There’s a direct line to the listener. It proves a great songwriter doesn't need a wall of sound to be heard. - WAX

Highway 61 Revisited
Bob Dylan
12
Highway 61 Revisited is the moment the folk tradition was forcibly shoved into the future. Dylan trades his acoustic purity for a wilder rock and roll sound that sways on the edge of chaos. The thinness of the organ and the biting electric guitars create a surrealist backdrop for some of the most dense lyricism ever recorded. It isn't a polite introduction, it’s confrontational. Dylan peppers his songs with a cast of outcasts and historical figures, blurring the lines between reality and a fever dream. It’s an explosive, cynical, and visionary record that redefined what a singer-songwriter was allowed to say and how loud they were allowed to say it. - WAX

Hejira
Joni Mitchell
11
Hejira is the sound of motion and the restlessness that comes with it. Joni Mitchell moves away from the piano-driven confessions of her past to embrace a colder swaying jazz-fusion. The fretless bass of Jaco Pastorius slides through the tracks like a car swerving through an empty highway, creating a liquid base for Mitchell’s wandering melodies. It captures the specific loneliness of watching your own life fly by. The lyrics are manuscripts of the soul, traded for the directness of her earlier work. It’s a sophisticated, sprawling exploration of independence and the transient nature of human connection. - WAX

Ys
Joanna Newsom
10
Ys is an exercise in maximalist storytelling that defies every convention of the genre. Joanna Newsom rejects the standard verse-chorus structure in favor of sprawling, orchestral epics that feel more like folklore than written words. The harp is the steady anchor, but the sweeping arrangements around it create a sense of scale that is almost overwhelming. It ensures a total immersion into its world. The record is defined by its density. The lyrics are a thicket of allegory and complex internal rhyme, delivered in a voice that is as polarizing as it is expressive. It’s an album that rewards the effort of close listening, revealing new layers of narrative and musical detail with every rotation. While many of its peers find power in what they leave out, Ys finds its strength in its abundance. It’s a dense, challenging, and utterly unique masterpiece that expands the boundaries of how saturated a song can be. - WAX

Astral Weeks
Van Morrison
9
Astral Weeks is a complete departure from the structure of the genre. Van Morrison moves away from the pop sensibilities of his early career with Them to create something that feels less like a collection of songs and more like a dream. The jazz-inflected instrumentation flows with a loose, improvisational energy, creating a backdrop that is both ethereal and grounding. It’s a rare side of singer-songwriter where atmosphere is the main goal. The power of the record lies in its fluidity though, Morrison’s vocals are ecstatic and raw, often abandoning traditional phrasing to chase a specific feeling. The lyrics capture a sense of longing that is difficult to pin down, existing in the space between the physical world and something spiritual. It’s a singular achievement that proves how far the singer-songwriter framework can be pushed before it breaks apart. - WAX

Tapestry
Carole King
8
Tapestry is the blueprint for the modern singer-songwriter. Carole King stepped out from behind the curtain of professional songwriting to reclaim her own voice, and the result is an album that feels like a warm, lived-in home. The production is sturdy and gives the songs a grounded, tactile quality that many in the genre trade for abstraction. It doesn't rely on the mystery of a persona; it relies on the strength of the melodies. The brilliance of the record is its accessibility. King writes about love, friendship, and transition with a directness that can make these massive pop structures feel like private conversations. There is a soulful grit to her vocals that adds a layer of reality to the perfect arrangements. It remains the gold standard for the pop appeal of the genre, while also keeping the personal weight. - WAX
Favorite of:
Kelly Cresswell
Snows of Yesteryear

Carrie and Lowell
Sufjan Stevens
7
Carrie & Lowell is a return to the roots of the genre, but it feels more like a haunting than a homecoming. Sufjan Stevens moves away from the maximalism of his past work to sit in a quiet, empty room with his grief. There is no spectacle to hide behind. The production is so thin and fragile that you can hear the air in the room and the mechanical hum of the recorders, which only makes the heavy subject matter feel more suffocating. The lyrics are blunt and avoid the typical metaphors of folk music, instead opting for the cold reality of hospitals and memory. It captures the specific, hollow feeling of losing someone you never truly had. While other albums on this list use instruments to fill space, Stevens uses silence to emphasize what’s gone. It’s a devastatingly lonely record that proves the quietest songs can carry the most weight. - WAX
Favorite of: Rachel Love

Blood on the Tracks
Bob Dylan
6
Blood on the Tracks is Dylan dropping the mask. After years of hiding behind surrealist folk-hero personas, he turns the lens inward to find a landscape that is completely broken. The songs move with a strange, non-linear fluidity. They shift from the past to the present in a single verse, mimicking the confusing way a person actually remembers a lost love. The beauty of the album is found in its jagged edges. While the acoustic arrangements feel warm, the lyrics are sharp. It’s an honest, bleeding portrait of a marriage disintegrating before our eyes. Dylan explores the space between love and resentment with a level of poetic precision that few others have ever reached. It is a sprawling, messy, and deeply human collection of stories. It shows that the best songs aren't written in calm moments, they are pulled out of the wreckage. - WAX
"Raw lyrics, beautiful melodies, and sympathetic production giving the music and, even more than that, the emotion room to breathe. And ‘Tangled Up in Blue’." - Ian Paul Sharp
"There are so many Dylan albums to choose from but here, he was just killing it! Nearly all of the songs turned out to be classics. My favorite remains "Shelter From The Storm" which is a masterpiece of Dylan's ability to write lyrics which sound simple but are really intricate at the same time. This is how I heard Dylan the first time and I remember that as I understood the lyrics more, the songs changed in their vibe and meaning." - JoeJoe S

Either/Or
Elliott Smith
5
Either/Or feels like isolation turned into music. Elliott Smith doesn’t make sadness feel dramatic, he makes it feel normal. That’s what makes the album hit so hard. The songwriting is incredibly intimate, to the point where it almost feels intrusive listening to it. Despite how stripped back and lo-fi it is, the album still feels full. Smith fills every song with layered melodies that are beautiful enough to almost distract you from how devastating the writing actually is. Either/Or captures the feeling of wanting connection while simultaneously hiding from it, and that contradiction is what gives the album so much weight.
"I picked this album because I had to pick something here, but I think any Elliott Smith album could be listed here. For my money, he is the most consistent singer-songwriter that ever lived. Everyone else on this list has released bad songs in their career, but not Elliott. We lost him way too young, but his career remains spotless. If you are reading this and haven't listened to him, I strongly encourage you to start literally anywhere and you'll find something worth your time." - Eric Stevenson (Of Pocket Vinyl)

Songs of Leonard Cohen
Leonard Cohen
4
Songs of Leonard Cohen is the pure essence of poetry in motion. The lyrics written on this album rival the words of the greatest poets, because in some ways Leonard Cohen is more of a poet than a musician. While the sound of this album is deserving of praise too, with its peaceful, but reserved atmospheric flourishes, this album is held up by Cohen's lyrics. They reveal the truth about the human condition through masterful imagery, and even greater storytelling. Vocally too, Cohen is raw and simple, but it only brings more attention to the lyrical brilliance of the album. The title of the album is very fitting, for these are simply, Songs of Leonard Cohen. Even if it was his first, he was perfectly conscious of his ability and wasn't holding back.
"I listened to this on cassette for years. It traveled (and the songs still travel) with me over so many years and experiences." - Orange Animal
"I am very late to this man's music. I only discovered him for myself two years ago, and this 1967 album sounds like it could have come out today. It's timeless in it's songwriting, structure, lyrics, even the recording. It has far less of those “this was recorded a long time ago” hallmarks of a lot of pre-2000 musical recordings, and I don't know why. It's truly one of the best albums of the 20th century, regardless of genre." - Eric Stevenson (of Pocket Vinyl)

Grace
Jeff Buckley
3
Grace tows the line between singer-songwriter and the rest of the music world. It is a demonstration of the diversity that comes with incredible songwriting. While it's far from a stripped back acoustic piece like many of the albums it takes influence from, the portrait of Jeff Buckley still holds through. His emotional resonance, even while being engulfed by an intense alternative rock soundtrack, shines through in massive part due to his songwriting ability. His vocals are also piercing in their beauty. There may be more technically impressive singers but there are very few with more beautiful voices. The album isn't a bastion of tradition, because that's not what it sets out to do. It's not a perfection of what's been done in the past, but a showcase of flexibility. The constant can get repetitive, and this isn't the constant. - WAX
"The music and songwriting flows amazingly, making the whole album dreamy and trippy. His voice is beautiful, raw and lyrical." - Asteroid Lily

Pink Moon
Nick Drake
2
Pink Moon strips the genre down to its barest form, the sharing of emotion with one another. Our humanity is defined by it, and yet so many of us choose to ignore it. Nick Drake was incredibly depressed while making this album. Although that state of mind is devastatingly morbid, it lets raw emotion come out in a way that it can't otherwise. That raw emotion is only enhanced by the musical choices on this album. While we can look at the wide range of artists working along genre lines Drake confines himself to the simplest form. Voice and guitar fill the sound of a vast majority of this album, despite that barrenness it manages to feel full. That fullness comes from the weight of emotion. Your brain fills in the rest via our innate sense of human empathy. What activates within us while listening to this album is what sets the genre apart, connection. - WAX
Favorite of: Rachel Love

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