48. “Coldest Winter,” 808s & Heartbreak
Released a year after Kanye’s mother’s death, “Coldest Winter” is filled with loss and a fear of never loving again after losing the woman he loved most in the world. Much of 808s is about women he’s loved in former relationships—and this could work as that, as well—but to end the album with a song dedicated to his deepest love, “Coldest Winter” is Kanye at his most fragile and terrified.
47. “Guilt Trip” – Yeezus
Yeezus is by far Kanye’s brashest album so far, so “Guilt Trip” is a bit of lightness in the album’s final act. Even though Kanye originally planned to use “Guilt Trip” on Watch the Throne, it would’ve fit far better on 808s & Heartbreak, as Kanye discusses trying everything he can to keep a women, before eventually giving up. In an album that sounds like it could’ve been made by an angry robot, “Guilt Trip” is one of the album’s finest examples of heart.
46. “Devil in a New Dress” featuring Rick Ross, My Beautiful Dark Twisted Fantasy
“Devil in a New Dress” sounds like a throwback to the soul samples of Kanye’s first three albums, taking Smokey Robinson’s version of “Will You Still Love Me Tomorrow?” and repurposing it with a sparse, great beat. Kanye’s part here is fun and depreciating (“I ordered the jerk, she said “you are what you eat”) as he deals with the duality of his latest romantic interest. But it’s Rick Ross’ phenomenal final verse that could very well be the best verse of his career, even though it’s focus of excess is thematically different than the rest of the song.
45. “So Appalled” featuring Swiss Beatz, Jay-Z, Pusha T, Cyhi The Prince, and RZA, My Beautiful Dark Twisted Fantasy
Following “Monster” on My Beautiful Dark Twisted Fantasy, “So Appalled” continues that haunted sound, while discussing the Dr. Jekyll/Mr. Hyde dichotomy of rap and success. Kanye points out that people want him to make fun tracks, but he wants to do something that means something, while Jay-Z contemplates whether it’s better to die young a hero or stay in the game and become a villain. “So Appalled” is both a contemplation of what rap has come to and an exaltation of how great it can be.
44. “Diamonds From Sierra Leone (Remix)” featuring Jay-Z, Late Registration
The original version of “Diamonds From Sierra Leone” is probably one of Kanye’s greatest, most focused tracks. But this remix, largely dominated by Jay-Z, starts with Kanye discussing the eponymous diamonds, then segues into Jay and Kanye getting derailed by getting into the inner workings of their careers and Roc-a-Fella at large. This remix feels like a splicing together of some of the best elements of the original, yet Jay’s verse, while still pretty great, doesn’t hold a candle to the verses on Kanye’s original version.
43. “Last Call,” The College Dropout
Recorded the weekend before The College Dropout was released, “Last Call” is an almost 13-minute-long autobiography of Kanye’s life so far. Kanye realizes this could be his one chance at making his own album, yet he’s still cocky enough to know it’s too good for that to be the case. “Last Call” follows Kanye from up-and-coming producer to the rapper who had to fight to get a chance. It’s easily Kanye’s least catchy song, but it’s still a fascinating history of the man who would become an icon.
42. “RoboCop,” 808s & Heartbreak
Many of Kanye’s songs are about falling for the wrong type of girl, knowing that she’s not right for him, but still going for her. “RoboCop” is Kanye realizing this same mistake, but by the end we see him figuring out enough is enough. Collaborator A-Trak has said that Kanye tried to orchestrate “RoboCop” like a TV on the Radio song, which is evident in the way the song constantly changes its direction. This shift is most obvious in the end when Kanye becomes bitter, laughing at the ridiculousness of the girl whose craziness he once found attractive.
41. “We Major” featuring Nas & Really Doe, Late Registration
The longest song on Late Registration, “We Major,” is a celebration of Kanye finally on his way to becoming one of the greatest rappers in the world. Kanye’s repeating of “we major” in the chorus comes with a sense of disbelief that he actually made it. Even though he’s still on the rise, he still brags that he called the album Late Registration because he’s taking everyone back to school. Yet it’s Nas’ incredible verse that shows that at this point, Kanye still has plenty to learn.