13 Saddest Kanye Songs Ranked

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This article will introduce you to the saddest Kanye songs from the artist’s extensive discography.

Recent times have seen Kanye West – or Ye as he is now known – experience a dramatic fall from grace. The controversial artist has seen his status and his wealth deteriorate significantly as he has alienated fans and business associates with some of his remarks.

This said, Kanye remains one of the most successful and most influential rappers and recording artists of our generation. And Kanye’s music still resonates with many people.

Over the years, Kanye has written a number of moving songs about love, loss, and heartache. These songs arguably show the artist at his best, revealing a deeper, emotional, and self-reflective side to Ye.

Let’s dive in and take a closer look at the best of Kanye’s sad songs.

Only One feat Paul McCartney

This unlikely collaboration between Kanye and the legendary songwriter Paul McCartney is one of the saddest Kanye songs.

Musically, the song is simple, with layers of vocoder vocals building on a gospel-esque organ chord progression. The simplicity gives the track a stirring simplicity and stillness. The organ is played by McCartney, with McCartney also providing backing vocals.

The track is sung from the perspective of Kanye’s late mother, Donda, looking down on her son from heaven. As Kanye fans know, Donda had an enormous influence on Kanye, demonstrating unwavering belief in him from a young age.

The 2014 song was released a single, and doesn’t appear on any of Kanye’s albums. It charted in countries all over the world, and topped the UK Hip-Hop/R&B singles chart.

Ghost Town

‘Ghost Town’ is a bittersweet song that blends feelings of mournfulness and triumph. The track comes from Kanye’s 2018 album, ye, which often touches on the artist’s bipolar disorder – a theme which comes through strongly in ‘Ghost Town.’

The Kid Cudi chorus reflects a sense of neediness and desperation, with the line, ‘I’ve been tryin’ to make you love me / but everything I try just takes you further from me.’

But despite the feelings of loneliness and neediness that come through so clearly in the chorus, the song ends with a bold, if slightly unhinged proclamation of liberation. This is summarised in the line, ‘I put my hand on a stove, to see if I still bleed / and nothing hurts anymore, I feel kinda free.’

An usual song that offers an insight into Kanye’s highs and lows.

Coldest Winter

A classic song about separation and heartbreak, ‘Coldest Winter’ is an example of Kanye’s simple yet effective songwriting. The song is stark and dramatic, with the prominent, pounding drums a stand-out feature.

The song epitomises the atmosphere of 808s & Heartbreak, with its iconic refrain ‘goodbye my friend, will I ever love again?’ 

The song laments two losses that Kanye endured in quick succession – the death of his mother Donda, and his breakup with his long term girlfriend and fiancé, Alexis Phifer.

A cold and stark song about grief and loss, which is undeniably amongst the saddest Kanye West songs.

Lost in the World feat Bon Iver

‘Lost in the World’ sees Kanye sample Bon Iver’s early hit ‘Woods.’ The original song featured mournful, repeating, layered vocoder vocals. Although those elements are still part of the song, Kanye introduces thumping drums to the track, taking it to a very different place from the original.

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The song represents an unexpected and surprising reinterpretation of the Bon Iver song, in which Kanye juxtaposes the original atmosphere and lyrics of the song with a whole new meaning.

Lyrically, the song has an almost apocalyptic feel, with the refrain ‘who will survive in America?’ The song also sees Kanye’s lyrics about building a city stand in sharp contrast to the Bon Iver lyrics about retreating to the woods.

The result is a unique and distinctly Kanye-esque atmosphere that combines melancholic and introspective elements with epic and uplifting production.

Pinocchio Story

‘Pinocchio Story’ is a live, freestyle track that closes Kanye’s legendary 808s & Heartbreak album. The track is deeply mournful and introspective, with Kanye singing ‘I just wanna be a real boy.’ The song features just a simple piano part with Kanye’s vocals on top.

In the song, Kanye laments an inability to find love, summarised in the line, ‘everything in the world figured out / but I can never seem to find what real love was about.’

The track reveals feelings of isolation and dislocation, as Kanye reflects that wealth and fame do not provide for his deepest need for love and meaning. Definitely one of the saddest Kanye West songs, and the perfect end to his classic heartbreak album.

Roses

‘Roses’ is a tender and beautiful song about Kanye’s grandmother reaching the end of her life in hospital. The song captures feelings of uncertainty, tension, and sadness, with a soaring gospel-influenced chorus.

The song is very effective at painting a picture that will be familiar to many – the drama and pain when a beloved family member is sick in hospital, and reaching the end of their life.

The track comes from Kanye’s 2005 album Late Registration. Its straightforward, confessional tone makes the song accessible and relatable, as well as moving in its simplicity. A classic amongst Kanye’s sad songs.

FML

‘FML’ is the only track on this list from Kanye’s The Life of Pablo album. The track opens with a slow, stunted sort of flow, and a heavily melancholic feel.

The lyrics are introspective and vulnerable, addressing the haters who want to see Kanye fail, as expressed in the refrain, ’they wish I would go ahead and **** my life up / can’t let them get to me.’ The track has that slow, dramatic feel that Kanye does so well.

The song sees Kanye touch on what is arguably one of his fatal flaws as he sings, ‘even though I always **** my life up / only I can mention me.’ The line suggests that although Kanye is aware that he makes mistakes, he is unwilling to acknowledge criticism from other people. In other words, Kanye is only the person who is allowed to criticise Kanye.

Say You Will

The opening track from Kanye’s acclaimed 808s & Heartbreak album, ‘Say You Will’ perfectly sets the tone for what is one of his most-acclaimed albums. The song has that characteristic slow and dramatic Kanye feel, which comes through strongly on several tracks on 808s.

The lyrics are ambiguous and a little mysterious, alluding to a relationship that Kanye is struggling to let go of. A subtle sense of desperation seeps through to create what is one of the rawest and one of the saddest Kanye songs.

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Welcome to Heartbreak feat Kid Cudi

The introspective and thoughtful ‘Welcome to Heartbreak’ sees Kanye reflect on his priorities in life, and decisions that have made his life feel empty and shallow.

The sentiment is summed up in the line, ‘chased the good life my whole life long / look back on my life and my life gone / where did I go wrong?’

Along with a Kid Cudi chorus, the track features a minor piano ostinato along with dramatic drums, creating that epic and mournful feeling that Kanye does so well throughout the 808s & Heartbreak album.

Runaway feat Pusha T

One of the most-streamed Kanye tracks on this list, ‘Runaway’ is a popular track off Ye’s acclaimed 2010 album My Beautiful Dark Twisted Fantasy

The song has that epic and dramatic Kanye vibe, with vulnerable and introspective lyrics. The lyrics see Kanye reflect on his shortcomings and failings, with the refrain making this clear: ‘I always find something wrong / you been puttin’ up with my **** just way too long / I’m so gifted at finding what I don’t like the most.’

The sentiment of ‘Runaway’ is summarised with Kanye begging his lover to run away from him. Those lyrics, along with the song’s dramatic march, create a truly tragic feel. The instrumental coda, with the piano ostinato, strings, and overdriven guitar solo is the perfect tearjerker outro.

It is interesting that Kanye uses the line ‘I’m so gifted at finding what I don’t like most.’ Although the line is clearly a comment about a personal flaw, he describes it in terms of being ‘gifted.’ Surely Kanye is one of the only people in the world who would say they have been gifted with a flaw!

Street Lights

A classic track from Kanye’s 2008 album 808s & Heartbreak, ‘Street Lights’ is a deeply moving song. The track has evocative, driving instrumentals, with distorted guitar, piano, and pounding drums repeating and building. The layers of female backing vocals that come in halfway through the track are heavenly.

The poetic lyrics of ‘Street Lights’ seem to touch on Kanye’s journey from the streets. The song, however, has a real ambiguity to it. In a sense, it is a song of triumph. Yet the instrumentals have a melancholic feel, with the refrain ‘life’s just not fair’ reinforcing that feeling.

Poetic and dramatic, ‘Street Lights’ is vintage Kanye, and well-known as one of the saddest Kanye songs. 

Bad News

‘Bad News’ follows ‘Street Lights’ on 808s & Heartbreak for a back-to-back melancholic moment on the artist’s definitive heartbreak album.

The simplicity of the song and its lyrics make it perfectly relatable with the straightforward refrain ‘real bad news.’ The evocative line ‘my face turned to stone when I heard the news’ is elegant in its poetic simplicity.

The track is a fairly fast tempo, and the stirring string melody that comes in around halfway through the song provides a tragic, orchestral feel. A classic track that is surely amongst the saddest Kanye West songs.

Blame Game feat John Legend

‘Blame Game’ is a sad, strange, and in many ways highly sophisticated song. The instrumentals rework the Aphex Twin song ‘Avril 14th’ with a sweet, meandering bassline. John Legend’s gentle vocals and beautiful cello melodies offset Kanye’s cold and bitter bars.

The song’s raw lyrics address a relationship that’s breaking down, with both parties seemingly practicing infidelity. As well as bitterness, the track features some earnest and heartfelt lines, including ‘we walk away like strangers in the street / gone for eternity, we erased one another.’

The song ends with a bizarre dialogue that’s as wild as it is sad. The conversation seems to be between Kanye’s ex and her new lover. The refrain ‘Yeezy taught me,’ despite coming across as somewhat egotistical, is strangely disturbing and moving in equal measure. The mood Kanye creates here is totally unique, making this song one of his best and most memorable sad songs.

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