Z LIST: The TOP 40 SADDEST Songs of All Time

Most people automatically assume I have a black heart and soul or that I’m dead inside and thoroughly incapable of experiencing any sort of feeling let alone unmitigated joy. Well, they’d be wrong. I feel, if you cut me I will bleed and while it’s true I’m rarely happy, I am however  able to experience the beauty of sorrow.

Here are the top 40 songs I put on when I want to revel in my pain.

40. Over the Rainbow – Harry Nilsson (1973)
Album: A Little Touch of Schmilsson in the Night
Saint Harry, he had the voice of an angel. He kills this version of Dorothy’s ode to freedom and makes it his.

39. Diamonds and Rust – Joan Baez (1975)
Album: Diamonds and Rust
This is a gorgeous and bittersweet song written about Joan’s relationship with Bob Dylan. The lyrics are so intimate and personal; for her to let us in to her private world with such generosity is a rare and beautiful thing.

38. Everything I Own – Bread (1971)
Album: Baby Im-a-Want You
One might think this is a song David Gates of Bread wrote about a failed relationship, when in fact he wrote it for his father who had just passed away, making this song doubly as poignant 

37. Ain’t no Sunshine – Bill Withers (1971)
Album: Just as I am
Wither’s had an amazingly sure and unique voice, one of the best singer songwriters of the era. This song is simply one of the best songs ever written about how it feels when you’re in love. The ‘I know’ section still gets me every time.

36 . I Can’t Tell You Why – the Eagles (1979)
Album: The Long Run
Timothy B. Shmidt’s high and delicate voice makes this song soar. The Eagles were breaking up during the recording of the album this song originates from (The Long Run) but they certainly went out on a high note.

35. Sorry Seems to be the Hardest Word – Elton John (1976)
Album: Blue Moves
This effort by John is one of my favourites and sounds distinct from his typical sound of that period. There’s a strange European quality to it, which tugs at the heart. When my parents used to fight, I always knew how my father felt, as he would inevitably play this record.

34. Alone Again (Naturally) – Gilbert O Sullivan (1972)
Himself
Classic 70s. Better have your razor blades and cyanide locked up when you play this one, it’s a major tear-jerker. “when she passed away, I cried and cried all day, alone again naturally.” *sniff*

33. Take the Long Way Home – Supertramp (1979)
Album: Breakfast in America
This was on the radio constantly growing up and I can remember many a drive with my parents in the twilight of the day cruising into the night while this song played in the background. It always made the hairs on the back of my neck stand up with a powerful combination of loneliness and yearning.

32. Theme Song to ‘Alfie’  – Cilla Black (1966)
Album: Best of Cilla Black
Great song, great movie and this version by Cilla Black is the best version. This is basically Burt Bacharach’s ‘Desperado’ preceding the Eagles by a good ten years.

31. These Arms of Mine – Otis Redding (1964)
Album: Pain in my Heart
No one could sing like Otis, he’d not only rip your heart out, but your guts and veins and soul and just leave you there slobbering in your own blood and tears.

30. Superstar – The Carpenters (1971)
Album: Carpenters
The classic scene in ‘Tommy Boy’ with Chris Farley says it all. The Carpenters were cool and Karen Carpenter had one of the greatest voices of all time…period. This is their best song. Karen knocks it out of the park on this one.

29. Take it With me – Tom Waits (1999)
Album: Mule Variations
When you listen to this one you’re left blubbering like a gut shot hound. This is Waits stripped down to the bone, he’s just singing to his wife from his heart and we’re lucky enough to be able to listen in

28. For no One – The Beatles (1966)
Album: Revolver
Even in its classical, icy, Britishness, this song still breaks you down. Paul’s voice is just so directed and wistful, pure genius.

27.  How can we hang on to a dream? – Tim Hardin (1966)
Album: Tim Hardin 1
Tim Hardin’s one of the most underrated songwriters of all time and this is a fantastic work of his. A private conversation between two struggling lovers set to music. Intense and immediate.

26.  Only love can break your heart – Neil Young (1970)
Album: After the Gold Rush
What more can you say? Neil Young cutting through all the platitudes and simplifying it all so we can understand. What else can break your heart after all?

25. Dolphins – Fred Neil (1967)
Album: Fred Neil
The lyrics are mysterious and evocative and his voice is just incredible. Neil’s another woefully underrated songster from the 60s and 70s and this tune’s my favourite of his.

24. Nuit sur le Champs Elysses (off of Lift to the Scaffold Soundtrack) – Miles Davis (1958)
Album: Lift to the Scaffold
Miles Davis is perhaps the greatest Jazz musician of all time and this piece of his from the soundtrack to Louis Malle’s first film is a great example of his brilliance. The tune just sounds like the night – shadowy, evocative and stirring.

23.  Sea and Sand – The Who (1973)
Album: Qudrophenia
Off of their classic Quadrophenia, this song has the perfect combination of yearning and rocking. None of the members of the band were any better than on this album. 

22. No Expectations – The Rolling Stones (1968)
Album: Beggar’s Banquet
The Stones finally were able to write their very own blues classic with this one. Robert Johnson would have been proud to write it. Every time I hear it, I feel my oaken soul ache within.

21. You Were Always on my Mind – Elvis Presley (1972)
Album: Separate Ways
Willie’s version is great, the King’s version is better. This is the ultimate expression of a man who fucked up. I don’t think anyone hasn’t felt like this at one point in their lives.

20. Hello Walls – Willie Nelson (1965)
Album: Country Willie: His Own Songs
Willie Nelson knows how to cut through to the heart of the matter, beautifully crafting this classic as if out of fine rosewood. It perfectly captures the loneliness one feels when you’re just roaming around your house a mere shell of your former self, left in the wake of broken love.

19. Ne me Quitte Pas – Jaques Brel (1959)
Album: Ne me Quitte Pas
Brel along with Serge Gainsbourg was France’s most beloved songwriter and this is his ultimate love song. The final lyrics translated are, “let me become the shadow of your shadow, the shadow of your hand, the shadow of your dog, don’t leave me, don’t leave me, don’t leave me”. I think that pretty much sums it up.

18. San Diego Serenade – Tom Waits (1974)
Album: The Heart of Saturday Night
This song is a masterpiece written by Waits when he was just a romantic kid. It’s sad and reflective and he brings an insight to matters of the heart which are astounding for someone so young.

17. Take this Longing – Leonard Cohen (1974)
Album: New Skin for the Old Ceremony
This is my favourite by Leonard Cohen (and I love all his stuff). When he asks for his lover to act with him ‘like you would do for one you love’ you immediately understand the situation. He’ll never get what he desires from her, but he can’t help but try.

16.  Caroline No – The Beach Boys (1966)
Album: Pet Sounds
Brian Wilson wrote this about his wife and her loss of innocence. It’s funny to think that, since they were both so young. Wilson wrote a million wonderful songs one more remarkable than the next, but this one captures that sense of loss in a uniquely sorrowful way.

15. Running out of Fools – Aretha Franklin (1964)
Album: Running out of Fools
The Queen of soul sings for broken hearted women everywhere with this one. Her voice is crystalline and assured and the lyrics are insanely good. Whoever she’s talking about in this song just got his ass handed to him.

14 – Many Rivers to Cross – Jimmy Cliff (1972)
Album: The Harder They Come
Cliff along with Marley are the two greatest Reggae artists of all time and this wistful ballad is perhaps his best song. It’s the perfect encapsulation of the struggle we all go through every day and how we must all inevitably endure or fade away.

13 – Lonnie’s Lament – John Coltrane (1964)
Album: Crescent
I first ran across this piece in sheet music form, I sat down to the piano and played it and was blown away before I even heard the record. From then on I became a huge fan of the man. Coltrane’s original sound is undeniable -  it stands apart from all the others in a way  both distinctly  human and elevated in its nobility.

12 – Overs – Simon and Garfunkel (1968)
Album: Bookends
The game is over, over, over. Paul Simon next to Dylan is perhaps the greatest singer songwriter that ever lived and this song is the ultimate song of a relationship that’s dones-ville, but the participants are just too filled with ennui to go their separate ways.

11. Late For the Sky – Jackson Browne (1974)
Album: Late For the Sky
Browne’s laid back vocal style and organic musical arrangement is both muscular and loose. This is one of my favourites of his, sounds like the soundtrack to a break up drive down the Californian coast.

10. Mama You’ve Been on My mind – Bob Dylan (1964)
Album: The Bootleg Series, Vols. 1-3 (Rare & Unreleased) 1961-1991
“I’d just be curious to know if you see yourself as clear as someone who has had you on their mind”…This kid was 22 years old when he wrote that. I dare you not to tear up listening to this one.

9. Time – Tom Waits (1985)
Album: Rain Dogs
This is another powerful song by the great Tom Waits off of his Rain Dogs album. It’s like a taught impeccably written short story set to music so filled with longing, it’ll destroy you. This song burns in your chest like a swallow of bourbon  like only bourbon can taste when you’re alone with yourself on a Saturday night.

8. I’ve Been Loving You Too Long– Otis Redding (1966)
Album: Otis Blue/Otis Redding Sings Soul
Perhaps the greatest love song ever written, sung by perhaps the greatest singer that ever lived.

 
7. Crying – Roy Orbison (1962)
Album: Crying
This I think is the best description of how it feels to swallow your pain and pretend that your world’s not collapsing in on itself when you meet up with the one who broke your heart. His voice is as expansive and filled with emotion as any great opera singer.

6. Funny How Time Slips Away – Willie Nelson (1964)
Album: Country Willie: His Own Songs
This song is just superb. It’s an interesting piece as it’s really many different types of love song rolled into one. It’s the sad longing love song, but it’s also the ‘fuck you’ love song. Above all else though, it’s insightful, ironic and just flat out brilliant. Written in a spare and meticulous fashion, it’s Nelson at his finest.

5. I want you – Elvis Costello (1986)
Album: Blood and Chocolate
The very, very best song ever written about the inner turmoil you experience obsessing on what your ex is doing with her new lover. Costello’s brilliance is that he never comes out and blurts it out, he just kind of hints and hints at it. You sense he wants to know the answer to his questions, but not quite as much as he doesn’t want to know. The crescendo is epic, as in any escalating argument of this type his rage keeps building until the bitter end when he inevitably explodes into silent resignation.

4. Desperado  – The Eagles (1973)
Album: Desperado
I am the desperado they’re singing about, so are millions of others, they were kids at the time and somehow managed to convey the inner feelings of us all with not a note or lyric wasted. It’s just literally perfect.

3. Only the Lonely – Frank Sinatra (1958)
Album: Frank Sinatra Sings Only for the Lonely
Sinatra’s voice could make you cry if he was singing from the phonebook. This song would crush the heart of the steeliest of sorts. Sung from the perspective of a broken man who is beseeching anyone that will listen to hold on to their love if they’re lucky enough to have found it.

2. I Threw it All Away – Bob Dylan (1969)
Album: Nashville Skyline
Nothing I can really say  about this song other than it is simply the best lyric ever written about the regret of having been careless with your life and love. Dylan is the single greatest lyricist in modern music and this is a great example of his ability to speak to the human condition like no other.

1. It Makes no Difference – The Band (1975)
Album: Northern Lights – Southern Cross
“Girl I love you so much and it’s all I can do, just to keep myself from telling you that I never felt so alone before”. If you ever feel the need for a cathartic cry, turn this song on and you’ll be cleansed. Unfortunately you’ll probably wind up with a headache from all the bawling. I recommend two Tylenol along with a tall glass of scotch.