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Top 30 Saddest Kanye West Songs

Kanye West cuts a sad, confused, and lonely figure these days. And it’s pretty traumatic to watch as a long-time fan. He used to be so fun and full of beans when he originally released his first album, The College Dropout, in 2004. 

The Kanye of today… 

More commonly known as Ye, he is a shell of what he used to be. Maybe the rigors of the record industry, a tumultuous divorce from Kim Kardashian, and living in the public eye are to blame.

The saddest Kanye West songs are like a glimpse into his life as an artist and human being, changing right before our eyes over the past 15 years. But the truth is that his saddest songs have a lot of depth. And, in some cases, are genius at work. 

No one ever accused Ye of being untalented; quite the contrary. So, here are some of Kanye’s saddest tracks that should’ve hinted at the direction his life was going to go.

Saddest Kanye West Songs

Top 30 Saddest Kanye West Songs

[nb]1[/nb] Street Lights


“Street Lights” sounds sad and reflective from the intro. But there is an uplifting positive in there somewhere. It was released in 2008 from his 808s & Heartbreak album that offered a more insightful vibe than some of his earlier releases. 

It’s a very lonely-sounding Kanye song that talks about him being left in the street lights. You can almost feel his loneliness and wonder what he was going through at the time. 

It’s emotional, relaxing, laid-back, and introspective… 

Everyone knows that Ye has no problem sharing his feelings now. But, back then, we didn’t understand the complexities and layers of his personality.

One thing that shines through in this track is the artistic integrity. And his fearlessness to try something new that didn’t sound much like his earlier stuff.

[nb]2[/nb] All Falls Down (feat. Syleena Johnson)


Although most of the sad Kanye West songs are all about his own life, “All Falls Down” is about the plight of black females addicted to retail, in his own words. It depicts a sad philosophy of African American women out there searching for something in high-end fashion purchases and not being fulfilled as people. 

It’s a very introspective song. He even touches on his own insecurities and the need to wear the best fashion brands so he can feel good about himself.

One of the most haunting parts…

The soulful chorus hook by female vocalist Syleena Johnson. “All Falls Down” was originally released back in 2004 on his debut album, The College Dropout

If you ever get a chance to catch the official video, you should. It’s a sad song about some real things, and that’s why we loved Kanye in the first place. 

[nb]3[/nb] Only One (feat. Paul McCartney)


I love Kanye West, and I’ve always loved Paul McCartney since I was a little kid. So, how could I not like “Only One,” which is a collaboration between these music legends? 

It’s very peaceful and introspective, and the moment the intro kicks in, you know it’s not a normal Kanye rap tune. I would say that it’s not rap music at all, and that’s okay. It’s short, punchy, and very soulful, although it is a bit surreal if you are a rap music head.

It’s one of his newer tracks…

You can hear that the moment you put it on. It was released from his 2021 Donda album and is a tribute to his daughter, North West, sung from the perspective of her late grandmother, Kanye’s mother, Donda. And, because the message is so real, it’s a very sad-sounding Kanye West song

[nb]4[/nb] Heard Em Say (feat. Adam Levine)


There’s an overriding sadness to “Heard Em Say,” featuring Maroon 5’s Adam Levine in the chorus. This is a quirky yet beautiful song that uses a soft and melodic yet melancholic piano sample from the 1977 Natalie Cole track “Someone that I Used to Love.” 

“Heard Em Say” was released in 2005 from his sophomore album, Late Registration. The line “Nothing’s ever promised tomorrow today” is a poignant message that leaves me guessing what Ye was talking about all these years later. 

If you like insightful raps with haunting yet melodic beats, this is the one for you. I like it when it takes me years to figure out a song. It shows great depth from the artist’s point of view when he made it. 

[nb]5[/nb] Ghost Town


There are many faces and styles to Kanye’s music. A great representation of that is 2018’s “Ghost Town” from the Ye album, his eighth studio record. Again, this is not Ye the “Rap Gawd” per se, it attempts to be more musical in its essence. 

From the opening beat, with swirling string samples, it gives off a sad yet thoughtful vibe. Most of his rap fans had stopped listening by this time. But there is way more to Ye than producing beats and rapping straight bars.

The raw approach to his vocals on this cut is unique…

And, in some places, it is really catchy. It’s the sort of tune that you have to listen to a few times to understand its vibe and message. But all the best sad Kanye West songs are like that. 

Is this a Kanye song I would pop in my car stereo on long drives? Hell, Nah! But it does have interesting things going on. 

[nb]6[/nb] Lost in the World (feat. Bon Iver)


Talking about unique production values. Nothing is more unusual yet insightful than “Lost in the World” featuring Bon Iver from his 2010 My Beautiful Dark Twisted Fantasy album. Nearly all the tunes on this project are experimental and unique in every way. 

At the time, most rap fans thought Ye had lost his mind, and we were probably right. But that doesn’t take away from his artistic flair and creativity. If anything, it bolsters it.

Again, it’s not classic Kanye in a rap sense…

But, in fairness, when did his music ever stay to the same vibe or formula? He has always progressed as an artist, but it’s safe to say that “Lost in the World” feels intensely sad from the outside. 

You could dance to this tune if you wanted to. But I think it’s deeper and more melodic than a dance song. However, that’s just my opinion. 

[nb]7[/nb] Coldest Winter


This track off Kanye’s 808s & Heartbreak album is another time when his fans didn’t quite understand what he was doing. But it all makes sense now we’ve all had over a decade to mull it over. 

This is one of the saddest Kanye songs in the sense that it sounded more like a dreamy EDM track than something that a rapper and Hip-Hop producer might make. 

It’s very cinematic in its conception… 

And it uses lots of distorted vocals and an array of frequency chords that make this something so eclectic and unique. If you listen, there is a great but sad story being told that is essentially about him mourning his dear mother’s death

The sonics are out of this world. If you play it full blast when you are lonely at home, it can take on a life of its own. Is it Rap or Electro-Pop? Probably neither, but who cares?

[nb]8[/nb] Runaway (feat. Pusha T)


The My Beautiful Dark Twisted Fantasy album is famous for throwing away the rule book in terms of what we expect from Kanye. 

But the truth is that the album has a very sad and melancholic vibe that is introspective and even slightly harrowing in spots. Quite possibly the best and one of the sadder tracks on the album is “Runaway,” featuring an excellent verse from Pusha T. 

It was originally released in 2010 and was quite different at the time… 

The song was widely acclaimed by critics and fans alike at the time. It’s even considered the best Kanye West song ever by certain sections of his fanbase. There is already a load of songs that will be remembered for a long time from this album, but “Runaway” might be the best. 

By this time, Kanye had lost some of his more hardcore rap-inclined fans. But, they were replaced by a wider and more rounded audience that was beginning to take to his work. 

[nb]9[/nb] Blame Game (feat. John Legend)


When “Blame Game” first came out in 2010, it was about his failing relationship at the time. It came across as a sad but beautiful Kanye song

The song, lyrics, and composition were a joint project by Kanye West and John Legend. The piano loop courtesy of Legend and his haunting vocals make this track a masterpiece, in my opinion. 

It took production values to another level…

The use of several samples that are meticulously mixed gives the composition real depth and brevity. The cameo at the end of the track by comedian Chris Rock is a bit lewd and dirty, but it plays perfectly into the track’s subject matter.

The dreamy melodies, cool vocals, and overall message in this song create something a bit sad, but not miserable. It might be one of the saddest Kanye West songs, but it’s far from being at the top of the list. 

[nb]10[/nb] Blood on the Leaves


“Blood on the Leaves” was first released back in 2013 from the Yeezus album. It famously used the Nina Simone sample from her “Strange Fruit” track which gives it a haunting and sad vibe

The lyrical subject matter touches on how fame in America can ruin personal relationships. It also makes harrowing comparisons to the lynching of black Americans before the civil rights act came into place.

The shape of things to come?

Kanye talks about how modern American society, especially for African Americans, is all about bleeding for corporate enterprises that are running our governments from the shadows. Greed, materialism, and the thirst for money and things are the cornerstones of Americana. 

This is one of Kanye’s most political tunes and albums in general and a taste of what was about to unfold in his life. Kanye is slowly but surely turning against the political hierarchy that controls America, and it’s probably not going to end well for him. 

[nb]11[/nb]Bad News


[nb]12[/nb]Welcome to Heartbreak (feat. Kid Cudi)


[nb]13[/nb]Pinocchio Story (Freestyle Live from Singapore)


[nb]14[/nb]Hey Mama


[nb]15[/nb]Real Friends (feat. Ty Dolla $ign)


[nb]16[/nb]Wolves (feat. Frank Ocean)




[nb]18[/nb]Violent Crimes (feat. Nicki Minaj)


[nb]19[/nb]I Wonder


[nb]20[/nb]FML (feat. The Weeknd)


[nb]21[/nb]Street Lights (feat. Alicia Keys)


[nb]22[/nb]Say You Will




[nb]24[/nb]Never See Me Again


[nb]25[/nb]Everything I Am


[nb]26[/nb]30 Hours


[nb]27[/nb]Famous (feat. Rihanna)


[nb]28[/nb]All of the Lights (feat. Rihanna)


[nb]29[/nb]Dark Fantasy


[nb]30[/nb]Ultra Light Beam (feat. Chance the Rapper)


Looking for More Sad Songs?

If so, check out the Best Songs About Crying, the Best Songs About Loneliness, the Best Songs About Pain & Suffering, the Best Songs About Unrequited Love, and the Best Sad Rap Songs for more heart-breaking song selections.

Of course, you need to hear them. So, why not take a look at our in-depth reviews of the Best Headphones for Hip-Hop, the Best Headphones for Music, the Most Comfortable Headphones, the Best Bass Earbuds, and the Best Sound Quality Earbuds that you can buy in 2023?

Saddest Kanye West Songs – Final Thoughts

The trials and tribulations of the life and times of Kanye West have been an ongoing drama series for the past 15 years. And it shows no signs of slowing down. He might not be the relevant artist he used to be, but no one his age is. 

Breaking ground in the music industry is for younger artists, not men in their 40s. The fact that he has stayed relevant for so long just tells you how special he is as a rapper, producer, and artist. 

Kanye West’s saddest songs are not necessarily about Ye being depressed or sulking. They are more about brooding and being introspective and insightful. For sure, he is not the hard rapper he used to be and has developed into a more rounded artist.

But that’s to be expected from a musical genius… 

Let’s hope he cheers up a bit and doesn’t do anything stupid, so he is still around to make some more albums and evolve his sound even more. Although, recent events may suggest otherwise.

So, until next time, happy listening.

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