32. “Amazing” featuring Young Jeezy, 808s & Heartbreak
As much as Kanye gets criticized for his actions, he’s also the first to admit that he’s a problem or that he’s wrong, as he does in “Amazing.” Even before the infamous Taylor Swift incident, he realized that his ego and his insistence to fight for what he believes in could end up being his downfall. While “Amazing” sounds like it could be the rare narcissistic song on 808s, Kanye never calls himself amazing on the song, but instead he sees his success despite his difficulties and his egocentric actions to be something truly amazing.
31. “On Sight,” Yeezus
Kanye has often said that he usually starts his albums off with something light, but “On Sight” starts Yeezus like a computerized car crash. Kanye begins Yeezus by making it intentionally hard to get into, beginning with anger, then teasing happiness with the interlude’s samples before snatching it back. In his first collaboration with Daft Punk since “Stronger,” Kanye ends “On Sight” with a dark, twisted homage to that song, destroying his past with Yeezus season swiftly approaching. “On Sight”—like much of Yeezus—is Kanye playing around with what people expect from him and twisting it into darkness.
30. “Welcome to Heartbreak” featuring Kid Cudi, 808s & Heartbreak
Only a year prior on “Good Life,” Kanye praised a life filled with women, new sports cars, and shopping sprees. The sequel to this, the comedown to this type of living, is “Welcome To Heartbreak,” in which Kanye finally realizes he has the life he’s always wanted and it’s not what he expected. Instead of cars and houses, he’s now envious of his friends who have kids. “Welcome to Heartbreak” is Kanye in introspective mode, trying to figure out who he wants to be going forward, confused by who he’s always wanted to be and who he wants to be in the present.
29. “The New Workout Plan,” The College Dropout
It’s insane to think that the man who made Yeezus considered making “The New Workout Plan” his first single. “The New Workout Plan” is Kanye’s most intentionally funny song, an incredibly sarcastic look at how women are perceived to be good for nothing other than their bodies by wealthy men and only want money, while he also lambasts those men for being interested in such gold diggers. “The New Workout Plan” is a departure for Kanye, even back then, but is a reminder of the great sense of humor Kanye occasionally has.
Would Kanye be such a big deal today if he didn’t have the attitude that he constantly exudes for better or for worse? Maybe not, but it’s his ability to be himself in pretty much every situation that makes him such a fascinating musician and celebrity. “Everything I Am” points out that he can’t be anyone other than himself and he shouldn’t try to be. Kanye even points out at the beginning of “Everything I Am” that his friend Common passed on the beat, but then he turned it into something positive, rather than a disappointment. For Kanye, the ability to spin the negative into positives has made him everything he is.
27. “See You In My Nightmares” featuring Lil Wayne,808s & Heartbreak
If 808s is Kanye going through the steps of loss, “See You In My Nightmares” is absolutely anger. He’s furious at the end of a relationship that he thought could last forever and his fury is filled with pain. Even though he claims that he doesn’t love the girl anymore, there’s still likely a splinter of love still in Kanye’s heart. Yet, no matter how much he rails against the end of the relationship, subconsciously she’ll still be on his mind. Lil Wayne’s contribution in the final verse is haunting and heartfelt, as he sounds like he’s trying to find reason after the relationship has ended, knocked for a loop, confused, and out for blood, all while tears are streaming out.
26. “All Falls Down” featuring Syleena Johnson, The College Dropout
Already in the second track on The College Dropout, Kanye starts discussing his conflicting relationship with money, to a point that his jeweler Jacob Arabo becomes a recurring character in his songs. Even before Kanye was the superstar he is today he said, “it seems we living the American Dream, but the people highest up got the lowest self-esteem.” Kanye doesn’t want to be held down by his money, but he can’t help wanting the best he can buy, even if he doesn’t have the cash for it, yet. While we see Kanye dealing with his many addictions throughout his albums, his love of money and his hatred of this love remains constant.
25. “Hell of a Life,” My Beautiful Dark Twisted Fantasy
Coming right after “Runaway” on My Beautiful Dark Twisted Fantasy, “Hell of a Life” is equivalent to running full-speed to the strip club immediately after leaving confession. “Hell of a Life” is a distorted dive into the darkest, most depraved regions of Kanye’s desires, one in which sex becomes his religion that makes priests faint. The song puts an entire lifetime into the span of one night, where you can enter the club single, fall in love with a porn star, get married, go on your honeymoon, and get divorced all before you leave. This is Kanye at his most nihilistic, enduring an entire life for the span of an orgasm.