Toast To THE Douchebag: Greatest Songs of Kanye West

Kanye West is an asshole. There is no need to sugar coat it. He’s a douche bag, and I don’t like douche bags. I don’t like douchebags in real life. I don’t like douchebag drivers, athletes, actors, or singers. But I love Kanye West. It says a lot about his musical talents that I love him so much given his personality. So I decided to create a bracket.

I got the idea after reading a fantastic article, where this guy did a top 64 March Madness style bracket of Jay-Z songs. I’m a huge Kanye fan, so I thought it would be fun to do the same. Me and my buddy A-Rod met up and did our own brackets, and this article is about mine. Alittle background on the bracket before we get started.

We decided on 48 songs. We felt that 64 was too many considering how many songs Kanye has released, but we also thought that 32 was too few considering how many great songs he has. We settled on 48, with the top 4 seeds in each bracket getting a bye. The main drawback of this is that it gives most of Kanye’s radio hits byes to the next round while his album songs duke it out early. But the more Kanye, the better. We then ranked the songs by the number of youtube views. Without further ado, here is the official Kanye West bracket.

Album Representation
The College Dropout: 8
Late Registration: 10
Graduation: 11
808s and Heartbreak: 5
My Dark Twisted Fantasy: 9
Watch The Throne: 5
We broke the brackets down by college year, since Kanye’s first few albums were named after college terms. We will start with the senior bracket.

Round 1
Senior Bracket
#8 Hey Mama vs. #9 Glory – Hey Mama is a great song. It’s made more hauntingly beautiful by the death of his mother. But Glory has it here. It’s a great beat, and Kanye kills it on the lyrics. Glory gets the win here.

#5 N***as in Paris vs. #12 Gone – This is a pretty easy one for me. I like Gone, but In Paris is arguably my favorite song off watch the throne. Given how much I like that album, it’s understandable that In Paris easily advances. That shit cray.

#6 Never Let Me Down vs. #11 Hell of a Life – A battle of new school vs. old school here. I like hell of a life: it’s a great sample and the lyrics are great, and the bit about fucking with the lights on at the end is hilarious. But Jay-z alone beats this song with his verse, and we haven’t even touched on Kanye’s verse, which we will later. Never Let me Down hold easily here.

#7 All Falls Down vs. #10 Roses – All Falls Down is a great song. Its Kanye’s 2nd radio hit. Roses is solid too, but it doesn’t hold a flame to All Falls Down. “She had hair so long that it looked like weave. Then she cut it all off now she look like Eve. And she be dealing with some issues that you can’t believe. Single black female addicted to retail.” Sorry Roses.

Junior Bracket
#8 Gorgeous vs. #9 Diamonds From Sierra Leone Remix – The Diamonds remix is ridiculous. But it’s mostly because Jay Z destroys. I mean, he’s not a businessman, he’s a business…man. But enough about Jay. Kanye is solid on this song, but he’s better on Gorgeous. “Get Caught with 30 rocks, the cop looked like Alec Baldwin”. Gorgeous takes it here.

#5 Diamonds From Sierra Leone vs. #12 Breathe In Breathe Out – Funny how both Diamonds songs are in the same bracket. This is a pretty easy slam dunk. Breathe In Breathe Out is a solid song, but Diamonds made Kanye a star. Easy choice, diamonds are indeed forever.

#6 Paranoid vs. #11 We Major – Paranoid is one of my favorite songs off 808s and Heartbreak, which for the record is my least favorite of Kanye’s albums. Easily. It’s a good song, but We Major destroys here. Kanye rips it up enough, and we Nas has a sick verse himself. Easy “upset” here. We Major gets the win.

#7 Jesus Walks vs. #10 Get Em High – A tough call here. Jesus walks is a big radio and fan favorite, and for good reason. The beat is fantastic, but lyrically wise, Kanye isn’t at his best. Speaking of at his best, there is Get Em’ High. The first two lines of his verse kills it more than anything in Jesus Walks, and for that, Get Em High gets the win here, in what many casual fans would consider a big upset.

Sophomore Bracket
Before I get started, I just want to point out that this is the best bracket of the tournament, and it’s not close. There are 5 songs that I could easily argue being in the final 4. Having said that, let’s get into it.

#8 I Wonder vs. #9 Everything I Am – A great first round matchup. I love both of these songs off of Graduation. There’s not much separating the two, but I’ll give the slight edge to Everything I Am. “People talk so much shit about me at barber shops. They forget to get their hair cut.” That’s pretty baller.
#5 Touch the Sky vs. #12 Two Words – Two words is a good song, but as you will see as a common thread, anytime Kanye uses big horns, I love it. And Touch The Sky is a perfect example of that. Pair him up with Lupe Fiasco, and this is an easy advance.

#6 H.A.M vs. #11 Welcome to The Jungle – Two songs off of Watch the Throne here. Well, the deluxe version anyways. I gotta give the slight edge to H.A.M here. It’s mostly cause of the beat, but it’s still pretty close. Hard as a Mother Fucker it is.

#7 Dark Fantasy vs. Devil in a New Dress – Two songs off MDTF here. It’s an easy pick for me. I love Devil in a New Dress, but Dark Fantasy might have been his best first song on an album. And Kanye knows how to open albums. Dark Fantasy gets the win here. “Can we get much higher?”

Freshman Bracket
#8 Champion vs. #9 New Day – For me, this is the closest first round matchup. Champion is a fantastic beat, and keeps me entertained throughout. On the other side, New Day is a slower song, but it’s just as catchy. Plus, Kanye wants his kid to be republican, so everybody he knows he loves white people. But…Champion gets the nod here. I want it to be my song whenever I win anything.

#5 Slow Jamz vs. #12 Celebration – A battle of two older songs. It is a celebration bitches, but Slow Jamz gets the win here. While Twista is most of this song, Kanye destroys his verse, and the beat is pretty sexy itself.

#6 Good Morning vs. #11 Big Brother – Another tough battle of Graduation songs here. Both are great, but I’m going to give the edge to Big Brother here. If for no other reason, it’s a love song to Jay Z, who’s a beast. “People never get the flowers while they still smell em.” Good Morning is a great opening, but Big Brother is the better song in the end.

#7 Lift Off vs. #10 Robocop – I like Robocop, but I’m more entertained by the first 10 seconds of Lift Off then I am of Robocop. For that, Lift Off gets the advantage.

Album Representation
College Dropout: 5
Late Registration: 5
Graduation: 9
808s And Heartbreak: 3
My Dark Twisted Fantasy: 7
Watch The Throne: 3

Round 2
Senior Bracket
#1 Stronger vs. #9 Glory – The number one overall seed is up, and for me, it’s done. I like Stronger, but it’s not one of my favorite songs. I don’t know what it is. On Glory, Kanye points out that his tuxedo at the Grammy’s was alitte Guido, but in fact, he could show up in a speedo and be looked at like a fucking hero. For that, I have to pull the trigger on the upset here. Glory wins.

#4 Monster vs. #5 N***as in Paris – Monster is nasty. Kanye talks about putting pussy in an ancient Egyptian coffin, but the best part of this song is Nikki Minaj. On the other end, In Paris is a great song, with a fantastic beat, and two great verses from Jay and Kanye. For that, In Paris gets the win.

#3 Otis vs. #6 Never let Me Down – Otis is super catchy, and it’s one of my favorite songs off watch the throne. But lyrically, Never Let Me Down takes it here. As Kanye so greatly puts it, “How could I complain bout what an accident did to my left eye. Cause look what an accident to left eye.” Otis goes down here.

#2 Flashing Lights vs. #7 All Falls Down – It may be the fact that Flashing Lights got overplayed by the radio, but this song doesn’t do it for me. While I’m not crazy bout All Falls Down, lyrically it raps circles round Flashing Lights. For that, it’s an easy victory for All Falls Down.

Junior Bracket
#1 Heartless vs. #9 Gorgeous – Got to pull another upset here. I like Heartless, it’s my favorite song off of 808. But honestly, that’s not saying a ton. And in the words of Kanye, “anyone who trying to blackball me forget about two things, my black balls.” The song is very creative, and so Gorgeous pulls the upset here.

#4 Heard Em Say vs. #5 Diamonds From Sierra Leone – I was shocked to see that Heard Em Day was a first round bye. Not because it’s not a great song, it definitely is. But Diamonds takes the cake here. It’s has afantastic beat, great lyrics, it’s just a great song. “Take your diamonds and throw em up like you bulimic, yeah the beat cold but the flow is anemic.” Diamonds moves on.

#3 Amazing vs. #11 We Major – Amazing is Kanye at his egotistical finest. I mean, it’s him talking about how amazing he is for 4 minutes. We Major is a different tone, and lyrically, he murders the song on his first line: “Feeling better than some head on a Sunday afternoon: Feeling better than a girl who says yes too soon.” I like We Major here.

#2 Homecoming vs. #10 Get Em High – I like Coldplay, but I could give Get Em High the edge here on guest stars alone, as Talib and Common rip it on this song. Having said that, this is a bracket about Kanye, and when I look at the lyrics, Get Em High still gets the edge here. The entire second verse is just ridiculous. Wherever you look at it, Get Em High has the advantage here. Another 2 seed goes down.

Sophomore Bracket
#1 All Of The Lights vs. #9 Everything I am – Easy choice here. All of the Lights kills Everything I Am in the first 10 seconds. As soon as you hear this song come on, your arm automatically turns the volume up. You can’t control it. Not that you would stop yourself if you could. Slam dunk here.

#4 Through The Wire vs. #5 Touch The Sky – Through the Wire is Kanye’s first radio hit, and of course it holds a special place in my heart. I have to echo his words in that song, “Thank god i ain’t too cool for the safe belt.” Thank god indeed, or else we would have never heard his genius. Having said that, it’s got to be Touch The Sky here. The beat is killer, and Kanye rips it up. “I’m trying to right my wrongs but its funny them same wrongs helped me write this song.” We haven’t even gotten until Lupe’s verse yet, which we will get to later. Hate to see Through The Wire go so early, but Touch the Sky is too good.

#3 Can’t Tell Me Nothing vs. #6 H.A.M – Another surprising slam dunk in the second round here. H.A.M is great, but Can’t Tell Me Nothing is in serious running for best Kanye radio hit. He’s fantastic on this song, and it’s an easy advance here. “I had a dream I could buy my way to heaven, when I awoke I spent that on a necklace.

#2 Good Life vs. #7 Dark Fantasy – This is such a sick matchup. Honestly, this is a final 4 matchup in my opinion. Good life has such a great beat. You have to put your hands up in the sky as soon as you hear that beat. But there’s just something about Dark Fantasy. I mean, “So Much head I woke up to sleepy hollow.” Seriously. That’s great. I hate to kick Good Life out this early. I really do. I went back and forth on this several times. But Dark Fantasy gets the win here.

Freshman Bracket
#1 Gold Digger vs. #8 Champion – Another close matchup here. Champion is a great song, and its got a great flow for the full 3 minutes. But Gold Digger was a game changer. It was a great beat, and I have enough lyrics on that song to get to the finals. Gold Digger takes the win here, knocking off one of my favorites.

#4 Love Lockdown vs. #5 Slow Jamz – Another case of me simply not being crazy about a radio hit here. Love Lockdown is a catchy beat, but lyrically, there’s not much going on here. Meanwhile, while Slow Jamz is mostly a Twista song, Kanye does have a light skinned friend looks like Michael Jackson got a Light Skinned Friend look like Michael Jackson. He popular, so Slow Jamz gets it.

#3 Runaway vs. #11 Big Brother – Big Brother is a good song, and a fantastic way to end one of my favorite albums, Graduation. Meanwhile, Runaway is a toast to the douche bags. A toast to the assholes. This song goes on wayyyy too long, but it’s still fantastic. Runaway gets the W here.

#2 Power vs. #7 Lift Off – I love the collaboration of Beyoncé, Jay, and Kanye here, and its a combination I hope will reunite after the most gangster baby in the world is born. But I had never heard anything like Power when it first came out. After my first listen, I immediately played it again. I was like “Wait, I didn’t just hear that epicness.” Yes, yes I did. The first 20 seconds of this song beat Lift Off in my opinion, so Power moves on here.

Album Reprentation
College Dropout: 4
Late Registration: 4
Graduation: 2
808s and Heartbreaks: 0
My Dark Twisted Fantasy: 5
Watch The Throne: 1
Sweet 16
Senior Bracket
#5 N***as In Paris vs. #9 Glory – Glory knocked off the #1 seed, but its Cinderella run ends here. In Paris just hits so damn hard, from the first second until the last. Plus 2 Blades Of Glory references?! Are you serious? Got to go with In Paris here.

#6 Never Let Me Down vs. #7 All Falls Down – All Falls Down was the song that proved that Kanye wasn’t just a flash in the pan, yet it’s not a favorite of mine. He’s got some great lyrics, but Never Let Me Down takes it here. He thanks the late father of his girlfriend at the time in the song, amongst several other ridiculous parts. The College Dropout hit goes on to the Elite 8.

Junior Bracket
#5 Diamonds From Sierra Leone vs. #9 Gorgeous – Another Cinderella run has to end here. Gorgeous is very catchy, but Diamonds is on another level. Not only is it a great song, but it has spawned great sample verses from Nas, Lupe, and Jay Z. That shows how much the beat is loved, and when you throw in some of his lyrics, this song has to be in the Elite 8. “What more could you ask for? The international asshole nah, who complain about what he is owed and throw a tantrum like he is 3 years old you gotta love it though somebody still speak from his soul.” I certainly do.

#11 We Major vs. #10 Get Em High – I’m honestly pretty bummed these two songs have to face off. These were two of my favorite dark horse songs to go deep. Both have great guest rhymes, in addition to Kanye’s great insightful words. Considering this is about Kanye, I have to move Get Em High forward. I’d put lyrics from this song in here, but the words themselves only tell half the story. The way he delivers the words takes it to a whole new level. Hate to see We Major go, but I gotta say bye to it.

Sophomore Bracket
#1 All Of The Lights vs. #5 Touch The Sky – I warnedyou that this bracket was brutal. I could easily see this being my top 4 songs in this whole bracket. The fact that I have to pick one out of this group is just unfair. Let’s start with the battle of the big horns. Both these songs have great beats, though I give the slight edge to All of the Lights for originality and kick. However, this edge isn’t as big as the edge I give lyrically to Touch the Sky. “Before anybody wanted K-west beats me and my girl split the buffet at KFC. Dog I was having nervous breakdowns like man these ninjas that much better than me?!” No Kanye, they are not. Touch the Sky gets the victory here.

#3 Can’t Tell Me Nothing vs. #7 Dark Fantasy – Can’t Tell Me Nothing may very well be my favorite radio hit of Kanye’s. The song just oozes baller. But Dark Fantasy is just one of those songs for me. It combines an incredibly catchy beat with lyrics that hit hard throughout the song. “Too many Urkel’s on your team that’s why your Winslow.” Another very close call, but I give the slight nod to Dark Fantasy here.

Freshman Bracket
#1 Gold Digger vs. #5 Slow Jamz – As tough as the last bracket was, this bracket is pretty easy for me. Slow Jamz is nice, but Gold Digger is just nuts. You will see him on TV, any given SundayWin the Superbowl and drive off in a Hyundai.” I could go on, but I’ve made my point.

#3 Runaway vs. #2 Power – Runaway is so different. The beat of words in the beginning is interesting, and for Christ’s sake, it’s a toast to the douchebags. But Power is just unprecedented. Kanye just has a way of knowing exactly what I want to hear before I know I do. 30 seconds into Power you know it’s a uniquely great song, and it just has to move on here.

Album Represntation
College Dropout: 2
Late Registration: 3
Graduation: 0
808s and Heartbreaks: 0
My Dark Twisted Fantasy: 2
Watch The Throne: 1

Elite 8
Senior Bracket
#5 In Paris vs. #6 Never Let Me Down – The beat to In Paris is at most 4 notes. It’s your typical Kanye beat. It’s so simple, yet ridiculously catchy. Never Let Me Down has some great lyrics, but I think it’s run in this tournament ends. In Paris is the best track off Watch The Throne, and there are some great songs there. In Paris gets a first class flight to the Final 4.

Junior Bracket
#5 Diamonds From Sierra Leone vs. #10 Get Em High – Diamonds From Sierra Leone is a masterpiece of storytelling. It takes you on a journey without you even knowing it. It’s a song that stays with you days after you listen to it. One of his best. Having said all that, I like Get Em High here. It has won 3 matches, and I haven’t even mentioned my favorite part yet. Kanye has possibly the most genius introduction to a guest star on a song ever. You can hear the song here. If you don’t want to listen to the whole masterpiece, just fast forward to the 2:05 mark. Go ahead….I’ll wait….Good stuff right? It has to be Get Em High here in a close one to the Final 4.
Sophomore Bracket
#5 Touch The Sky vs. #7 Dark Fantasy – When I started to break down this bracket’s sweet 16 section, I thought that Dark Fantasy was the underdog of the 4. However, I have thought about this longer than any other part of the bracket, and I’ve convinced myself that Dark Fantasy has it. I love Touch the Sky. Love love love it. Lupe kills it here, and Kanye is great. But there’s just something about Dark Fantasy. I can’t quite put my finger on it. It’s just a fantastic song. Plain and simple. It has to move on, even over a great song like Touch The Sky.
Freshman Bracket
#1 Gold Digger vs. #2 Power – The only chalk matchup here as the top two seeds have made it to the end. And rightfully so too. As I’ve mentioned before, I love how unprecedented Power is. It’s just so epic, and one of those songs you will hear for years. Then there is Gold Digger. A song that even the people he’s hating on in the song(the diggers) love. That really says something there. That’s Kanye in a nutshell. No matter how much you want to hate him, you have to love him. For that, Gold Digger moves on.
Album Representation
College Dropout: 1
Late Registration: 1
Graduation: 0
808s and Heartbreaks:-0
My Dark Twisted Fantasy: 1
Watch the Throne: 1
Final 4
#5 In Paris vs. #1 Gold Digger – We have the new Kanye vs. the old Kanye here. Which one gets the nod? In Paris is a phenomenal song, but a good part of that is the incomparable Jay Z. Meanwhile, on Gold Digger, while Jamie Foxx provides the catchy chorus, it’s all Kanye on the mic. Not only that, but if you have never yelled “we want pre-nup” when Kanye tells you to say we want prenup: raise your hand. Now take that hand and slap yourself in the face for lying to me. In Paris’s run ends here. Gold Digger moves on to the finals.
#10 Get Em High vs. #7 Dark Fantasy – A matchup here of two non-radio hits in the final four. Dark Fantasy has already made its way through one of the hardest brackets ever, and yet, it won’t be going any further. Get Em High has made it all the way to the final 4, and I haven’t even mentioned Talib and Common’s verses here. “Real rappers is hard to find…like a remote.” So simple. So sick. As much as I absolutely love Dark Fantasy, Get Em High moves to the finals. It has a beat, flow, and lyrics unlike any other Kanye song.
Album Representation
College Dropout- 1
Late Registration-1
808s and Heartbreaks-0
My Dark Twisted Fantasy-0
Watch The Throne-0

#1 Gold Digger vs. # 10 Get Em High – The ultimate David Vs. Goliath in the final. We have one huge radio hit versus a song that most of the common radio audience hasn’t heard. A top seed in the bracket versus a double digit seed. Well anyone who knows the story of David vs. Goliath knows the outcome here. Gold Digger is fantastic, and a song that I will be listening to until I die. The chorus is catchy, the lyrics are great. It’s one of Kanye’s best older songs. But then there’s Get Em High. Its old school Kanye, where his incredible flow is only matched by the wittiness of the lyrics. The way he delivers those opening two lines makes you realize that this is going to be a great song. Tag on Talib and Common, and it’s hard to find a better song. I personally can’t, and for that, the winner of the Kanye West bracket is: Get Em High.
Thank you if you made it to the end, I hope you enjoyed my bracket. My buddy did his own bracket, and his final four were All Falls Down, Power, Diamonds, and Through The Wire, with Through The Wire beating Power in the finals. I can’t argue with much there, and that’s the beauty of a project like this. There is no right or wrong answer. In the end, we all win. Thank you Kanye. Here’s hoping I release a sequel to this bracket in 10 years with a whole new list of songs. Keep it up sir. Thanks for reading.

Let me know song you think is Kanye’s best the comments!

Previous post

ANCHORMAN 2 is Actually Going to Happen! YES!!!

Next post

Movie Review: MIRROR MIRROR is beautiful, family fun

The Author

Kevin Taylor

Kevin Taylor

I grew up in the south, raised watching TV, Movies, and Sports. Entertainment is my life, and I can't imagine what my life would be like without it. I'm a USC grad, and proud to be a Trojan for life! Some of my favorite shows include South Park, Always Sunny, Dexter, and How I Met Your Mother, which I write a weekly recap of here. I also play and report on poker for a living. Its a hard way to make an easy living!