What Is The Best Kanye West Song of All-Time?

By Eóin Donnelly

There are two types of people in this world: those who stand up and applaud the giant leaps Kanye West has made for mankind, and the ignorant. At first glance, Kanye may appear immature, which is a pebble to a boulder compared to the most egregious comments made by his detractors. However, even a cursory survey of his art and the people he has inspired- including one Elon Musk– is more than enough to confirm his status as 21st century pop culture’s most impactful figure. Aldous Huxley once said that the secret of genius is to carry childlike enthusiasm into old age. There are certainly parallels to be made with Kanye West, the self-professed genius who is as likely to be dragged kicking and screaming from the party as he is to be the star of the show. These contradictions in his character, explored and dissected so beautifully through the curious power of sound, are what makes his artistic content so continually compelling.

When I seen ‘Kanye Madness‘ trending on Twitter this week, I feared the worst. With Yeezy Season approaching again- I’m excited beyond description for what comes of those studio sessions atop a Wyoming mountain– this was the worst possible time for another mental breakdown. Silly me. All ‘Kanye Madness’ represents is a clever intersection between hip-hop and college basketball’s March Madness, a bracket of Kanye West’s best songs which are pitted against each other until there’s one winner. Well, when I say best songs that is according to Missouri radio host Carrington Harrison, who actually did a great job. Of the 64 songs included, only the graceful elegy ‘Saint Pablo’ struck me as a glaring omission. And ‘Fade’ come to think of it, for the simple and indisputable fact that its video is the eighth wonder of the world. I digress. Round-by-round, song-by-song, I am going to crown my favourite Kanye West song of all-time… all-time! This is a huge undertaking I will probably- no, DEFINITELY- regret when my fingers go numb but here goes…

Round 1

Can’t Tell Me Nothing v Amazing

An easy one to begin. ‘Can’t Tell Me Nothing’ is the runaway champion here. It happens to be Kanye’s favourite Kanye song, so we can presume it’s his favourite song period. He’s got good taste. There are no Ten Commandments of Making Great Hip-Hop, but if there were then “grab the listener with your first lines” would be right up there. Is there a better couplet to summarise the tension in being a rapper than “I had a dream I could buy my Heaven/When I awoke I spent that on a necklace”? With a spot in classic comedy The Hangover it is hard to imagine Graduation standout ‘Can’t Tell Me Nothing’ as unfamiliar to even the most unschooled of rap fans, but for Kanye newcomers all the most essential ingredients are there to lure you in. There’s the soulful production, the subtle philosophical musings (“To whom much is given, much is tested”), inspirational Instagram-ready captions (“This is my life homie, you decide yours”), pop culture references and humorous bars galore (“So if the devil wear Prada, Adam Eve wear nada/I’m in between but way more fresher/With way less effort, ’cause when you try hard/That’s when you die hard”) and one of his best-ever hooks. Is Kanye a hypocrite on ‘Can’t Tell Me Nothing’? Yes, but he knows it, and that’s why we love him.

WINNER: Can’t Tell Me Nothing

So Appalled v Never Let Me Down

My Beautiful Dark Twisted Fantasy is a perfect album, but if I were to pick a song I was least enthusiastic about it would be ‘So Appalled.’ Nevertheless, it is still a great song on a perfect album. With both songs adorned by Jay-Z verses, this is another easy decision as ‘So Appalled’ features my all-time favourite Shawn Carter lyric: “Dark Knight feeling, die and be a hero/Or live long enough to see yourself become a villain.” Damn. Moreover, the story of Cyhi The Prynce’s guest verse is the stuff of legend. Eight years on, you only need to pay attention to a standard 24-hour news cycle to conclude that ‘So Appalled’s’ thesis statement has never been more true: life can be sometimes ridiculous.

WINNER: So Appalled

Last Call v Hey Mama

As the final song on Kanye’s debut album The College Dropout, ‘Last Call’ is most notable for its eight-minute monologue which lets you know in no uncertain terms how crucial Kanye’s arrogance is to his success. Without it, he never would’ve had an album in the first place. Laid out in minute detail on ‘Last Call’, Kanye’s struggle to make it in music is the story of the ultimate underdog ascending to rap royalty. Context aside however, ‘Hey Mama’ is a classic Kanye track that could make Medusa bawl her eyes out. As maternal tributes go, only 2Pac’s ‘Dear Mama’ comes close. Since his beloved mother Donda died in 2007, Kanye has never been the same, and neither has this song. Those who roll their eyes at hip-hop’s poetic value, laying blame at its doorstep for the source of all misogyny and violence, miss the forest for the trees. “As we knelt on the kitchen floor/I said mommy I’ma love you ’til you don’t hurt no more/And when I’m older, you ain’t gotta work no more/And I’ma get you that mansion that we couldn’t afford.” If those lyrics don’t warm your heart, then watch the video below and tell me Kanye is anything less than a hugely positive role model to sons all over the world. And I will fight you to the death.

WINNER: Hey Mama

Devil In A New Dress v Real Friends

Here we are- the first real dilemma. ‘Real Friends’ represents a side of Kanye that all too many people are sadly unaware of, a somber exploration of the lonely side of fame that is all the more haunting owing to Kanye’s incarceration in a mental health facility just a few months later. I really love this song and in a different mood I’d decide differently, but I’ve got to give the edge to ‘Devil In A New Dress’, a Beethoven-esque masterclass in Kanye West samples dissolving into a Mike Dean guitar solo that could awake Jimi Hendrix from the dead. “How she gon’ wake up and not love me no more?/I thought I was the asshole, I guess it’s rubbing off/Hood phenomenon, the LeBron of rhyme/Hard to be humble when you stunting on a jumbotron”. Kanye’s wit is incredible and that only scratches the surface on a song lathered in self-aware, sardonically biting lyrical gems over the angelic tones of Smokey Robinson. Try as I might to judge each song on its own merit, its impossible to separate ‘Devil In A New Dress’ from its genius sequencing, sandwiched in between ‘So Appalled’ and ‘Runaway’ in what may well be the strongest three-song stretch in hip-hop history. Rick Ross’s knockout punch of a verse brings the curtain down on an orchestration that is devil by name but divine by nature.

WINNER: Devil In A New Dress

Crack Music v New Slaves

An interesting match-up that says a lot about what kind of Kanye fan you are. Are you a member of the ‘I miss the old Kanye’ brigade, or do outlandishly experimental adventures like Yeezus excite you more than attempts to recreate the chipmunk soul horse he rode in on? As much as I love Kanye’s early work, I love his music most when he lets his rough edges shine, teetering at the edge of reality’s cliffside enough to push the sonic parameters of hip-hop but with acrobat-level balance that makes everything my ears are experiencing seem like some grand illusion that words fail to describe. Though it is his most divisive work, Yeezus is a work of genius and I will explain why some day soon (possibly for the five-year anniversary). ‘New Slaves’ is the perfect metaphor for the dichotomy of chaos and control, rage and grace, and the “I dare you to like me” attitude paired with musical mastery that makes it nigh-on impossible not to at the heart of Yeezus. It is a mark of how deep Kanye’s musical toolbox is that he finds ways to incorporate 60’s Hungarian rock music in a contemporary hip-hop album. The way the thumping beat on ‘New Slaves’ drum-rolls away into first a rousing Frank Ocean solo and then a bizarre, almost supernatural sample from Omega’s ‘Gyöngyhajú Iány’ captivates me in a way not analogous to anything else I’ve encountered in music. To summarise it I would say “what the fuck is this? I like it.”

WINNER: New Slaves

Flashing Lights v Famous

What I imagine choosing your favourite child is like. Objectively speaking, there’s very little to separate these songs, which both reside in the upper echelons of Kanye’s greatest party pieces. As a caveat, however, music is not objective. To a large extent, our enjoyment of certain songs over others depends on our serotonin levels, the memories attached to them and various other purely subjective measurements that say nothing of lyrics, production or songwriting. For that reason, and in spite of ‘Famous’ being perhaps Kanye’s most accomplished marriage of maximalist composition and popular appeal, ‘Flashing Lights’ wins every time because it reminds me of the two best things in life: good friends and good times. When whiskey is around and aux cord duties call, ‘Flashing Lights’ is always one of the first added to the queue. Ocean views, favourite authors and breezy sunshine; Kanye said it best: why can’t life always be this easy?

WINNER: Flashing Lights

Big Brother v Love Lockdown

I appreciate the sentiment of Kanye’s ode to Jay-Z, particularly as their acrimonious fallout shines new light on their relationship, but like the cognitive cancer masquerading as a reality TV show I’ve never cared much for ‘Big Brother’. Like Yeezus, I will also be writing a piece on 808s & Heartbreak as its ten year anniversary approaches. Rightly voted as one of Rolling Stone’s 40 most groundbreaking albums ever made, its lead single ‘Love Lockdown’ was an artistic reinvention and entirely original work that placed Kanye in a league of his own. This was not a man chasing the ghosts of Tupac of Biggie Smalls or the rhyming accomplishments of Jay-Z or Eminem. Eschewing rap completely, on ‘Love Lockdown’ Kanye embraced melody and an abrasive, electronic fog of bleeps and tribal drums that reflected his isolation in the wake of romantic heartache. Compounded by the grief of his mother’s untimely death, 808’s elevated the much-maligned technology of auto-tune to an art form. ‘Love Lockdown’ struck a secret treasure chest à la El Dorado that is still mined for artistic gold today. Some say Kanye lacks talent while in the same breath voicing their admiration for Drake, Kid Cudi, The Weeknd, Post Malone, Lil Yachty, Frank Ocean, Lil Uzi Vert, Future, Lorde, Travis Scott, 21 Savage or any number of contemporary artists that its difficult to imagine existing, at least in their known form, without Kanye and 808’s & Heartbreak. In hastening to drive home a point I risk condescension, but you must know you are wrong. One begets the other, and another, and another, and another, and another until it’s difficult to trace where the root innovation even began. Eight millennia on from Genghis Khan, 8% of people living in his former Mongol empire are said to be descendants of him. In the year 2808 I suspect our musical landscape and ‘Love Lockdown’ will bear a similar relationship.

WINNER: Love Lockdown

Through The Wire v No Church In The Wild

The time between understanding your potential and making it reality is nothing but purgatory. After years of knockbacks and sniggers from record label aristocrats, it took a literal waiting room for Kanye to finally escape life’s waiting room and walk through the golden gates of self-actualisation. Producing beats at 3am is the kind of hustle that landed the socially awkward Kanye in the same studio sessions as Jay-Z and The Black Eyed Peas, but on October 23 2002 it nearly killed him, falling asleep at the wheel of his rented Lexus and ending up requiring reconstructive surgery to have his jaw wired shut in the same hospital that Biggie Smalls died. Lucky to be alive, Kanye remained undeterred in his dream to be a rapper. Clasped in the jaws of death, Kanye was imbued with sabre-tooth ambition that dwarfed his diminutive stature. “Nothing in life is promised except death”, said Kanye on the moment that changed his life. The numbing effect of novacane was probably still fresh when Kanye made his debut single ‘Through The Wire’ two weeks after the accident. Against doctor’s orders, Kanye dusted off his trusty collection of soul samples, manipulating Chaka Khan’s ‘Through The Fire’ with surgical precision offset by a clunky flow and lisped delivery through his still wired shut jaw. Not that his unpolished rapping mattered. We the people felt the passion, Roc-A-Fella finally gave him his record deal, and the rest- as Kanye raps- was “history in the makin’, man.”

WINNER: Through The Wire

All Falls Down v Addiction

A certain top five entry on Kanye’s longest album, ‘Addiction’ is an incredibly relatable rumination on the perils of temptation and is one of Kanye’s most underrated songs. Hip-hop, however, is a beast of context and true to Kanye’s unique cultural influence, ‘All Falls Down’ was a lyrical earthquake that shifted the foundations of an entire genre. “We all self-conscious, I’m just the first to admit it” is a simple line, but it may well be the most important of Kanye’s career. By using the third single of his debut album to explore his materialistic flaws- and America’s- Kanye popularised the notion that vulnerability and hip-hop stardom are not mutually exclusive like no other before him. For a generation accustomed to hearing Drake leave drunken voicemails to his ex mid-song this may seem axiomatic, but it wasn’t always the case. Looking in the rear-view mirror it’s clear that Kanye surveyed the testosterone overload in early 2000’s hip-hop and thought it’s time to put the ‘me’ back in rhyme. By revealing the vacuous underbelly of the American Dream, all inhibitions fell down. That’s how you set a party off right.

WINNER: All Falls Down

Monster v Heartless

It depends what mood I’m in. I’d already decided ‘Monster’ before I gave the songs another listen and ended up changing my mind. If there were such a thing, ‘Monster’ would be a unanimous vote on the Hall of Fame of posse cuts. Playing up Kanye’s Hyde for the sake of some self-referential entertainment (“Everybody knows I’ma motherfuckin’ monster/I’ma need to see your fuckin’ hands at the concert”), ‘Monster’ is a fulcrum of the dark portion of My Beautiful Dark Twisted Fantasy. Kanye’s introductory verse wears the devil’s cape well, with the best known usage of the word ‘sarcophagus’ in the history of the English language , while Jay-Z carries the baton with aplomb. However, Nicki Minaj’s bipolar verse is the stuff of hip-hop folklore, one so good that Kanye considered taking it off the album to save his own face. Without it, MBDTF wouldn’t have quite been the same.

Despite all that, I have to opt for ‘Heartless’, the third most successful single of Kanye’s career. It also happens to be the catchiest song he’s ever made, and perhaps his greatest video also. With its Broadway-style chorus and a chug-chugging beat that sounds deceptively happy, ‘Heartless’ is like Thomas The Tank getting his heart broken. To the Kanye haters- how could you be so heartless?

WINNER: Heartless

Drive Slow v Highlights

A pretty weak pairing. Neither of these songs are anywhere near Kanye’s best. ‘Drive Slow’ is a little safe for my tastes, so I’ll opt for ‘Highlights’. No other rapper alive could pull off the infamous GoPro lines as hilariously as Kanye. Hopefully the Anchorman 2 cameo was a sign of things to come. I need a Step Brothers sequel where Kanye and Will Ferrell end up sharing a bunkbed. I’d be willing to die for that.

WINNER: Highlights

Runaway v Blood On The Leaves

Two all-time favourites. It’s a shame they had to square off so early. As I wrote earlier, subjective feelings are very much a factor in weighing up preference. If I was a famous MMA combatant I’d have to pick ‘Blood On The Leaves’. It would remind me of all those slow tunnel walks, marching out to that insanely primal beat drop on 1:05 and bashing boy’s heads in. Its balance of cathartic violence and serene contemplation is what the best walkout tunes are made of. I’m pretty pacifist though. ‘Runaway’ wins. Raise your glass to all the douchebags, assholes, scumbags and the jerk-offs that never take work off. They have some good qualities too.

WINNER: Runaway

Blame Game v Roses

Whatever you do, never ever ever ever skip the Chris Rock skit at the end. It’s the best part. Yeezy taught me.

WINNER: Blame Game

Good Life v Celebration

Both songs are all about celebration, but its not the namesake that does it best. If any song sums up what Kanye was trying to achieve with Graduation, it’s ‘Good Life’: “50 told me, go ‘head, switch the style up/And if they hate them let ’em hate and watch the money pile up/The good life”. Ironically, it was Kanye’s third album that essentially ended Curtis Jackson’s career, emerging victorious over Curtis in a much-hyped sales war that 50 Cent bet his career on. With smash crossover hits galore like ‘Good Life’, the gangster zeitgeist of hip-hop was instantly upended as every record label in the country recalibrated their idea of what it means to be a rap superstar. No longer was a drug dealing past, a prison stint or Timberland boots a prerequisite for rap stardom. Atop a stellar Michael Jackson sample, ‘Good Life’ was arena-ready hip-hop, a new formula where rap and mainstream radio could co-exist. Has Kanye ever been as happy as he is in this video?

WINNER: Good Life

The Glory v Get ‘Em High

Between lead single ‘Through The Wire’ and his debut album, Kanye’s rapping came on leaps and bounds. Charm in abundance can go a long way, but ‘Get ‘Em High’ proved Kanye had developed the skill to go along with it. Not even hip-hop purists could say he was outshined by fellow Chicago natives Common or Talib Kweli. Stoners roll up.

WINNER: Get ‘Em High

All Of The Lights v School Spirit

You already know the answer. I get goosebumps every single time the ‘All of the Lights (Interlude)’ fades into the main song. Elton John, Rihanna, Alicia Keys, John Legend, Kid Cudi, Drake and Fergie are just some of the names recruited for this maximalist symphony, a smorgasbord of megastars so peripheral to the song’s epicentre you barely notice who is who. That is not to trivialise their contributions, with each and every piece of melody, percussion and harmony on ‘All of The Lights’ adding up to an irresistible product with a very long shelf life. Kanye always gets the best out of Kid Cudi. Weaving a custody battle tale that serves as a metaphor for the irreconcilable differences between Kanye’s inner child and his relationship with public perception, ‘All of The Lights’ is a hugely dramatic and audacious song with a palatial production to match. I like it. I like it a lot.

WINNER: All of the Lights

Jesus Walks v Murder To Excellence

Bom-bom-bom-bom-bom. The sample God strikes again, sprinkling nightclubs with an uplifting slice of gospel magic to dance to in between songs about eating ass, killing dudes and downing jägerbombs. Balance is the spice of life. Blasphemy it may be, but I love this song more than Jebus. In layman’s terms, rapping about Jesus isn’t exactly the blueprint for being the cool kid in class. But Kanye dropped out of college after all, earning a reputation for his enormous testicles from day one, releasing ‘Jesus Walks’ as the fourth College Dropout single at risk of ridicule: “So here go my single dog, radio needs this/They say you can rap everything except for Jesus/That means guns, sex, lies, videotape/But if I talk about God my record won’t get played, huh?” There’s your daily reminder that radio does not serve the evolution of humanity. Turn it off and hear Yeezus preach.

WINNER: Jesus Walks

Street Lights v We Don’t Care

Another contest where temperament is the referee. I’m in too good a mood of late to be listening to ‘Street Lights’, but it’s been such a reliable source of comfort in tough times that I can’t show it the red card, even if ‘We Don’t Care’ has serious legacy value as the opening song on Kanye’s debut album. Plus, it’s the only Kanye song that I can say feels written by John Lennon beyond the grave. Like the best sad songs, ‘Street Lights’ is too breathtakingly beautiful to stay that way. Simplicity is genius.

WINNER: Street Lights

We Major v 30 Hours

I’m gonna cheat a little bit and pretend that ’30 Hours’ is the Soundcloud version and not the one that made it on to The Life of Pablo, with its meandering outro that wasted the wonderful gift of a Kanye & André 3000 collaboration. Fans of the ‘old Kanye’ will like this one. With Kanye’s trademark sampling style as the backdrop, ’30 Hours’ finds Kanye wistfully reflecting on a past relationship during the nascency of his career when he had to drive 30 hours from L.A. to Chicago to see his girlfriend. Allow me to blow your mind: that sample isn’t actually saying “30 Hours.” Kanye’s ear for samples is unparalleled. I want more of this Kanye on the next album. Yeezy season, hurry up.

WINNER: 30 Hours

Stronger v Black Skinhead

Kanye features very heavily in my gym playlist, and by twist of fate these happen to be my two favourites. It feels perverse to kick out arguably Kanye’s biggest song in the first round but I’m gonna do it anyway cos ‘Black Skinhead’ is all about not giving a fuck what anyone else thinks and I don’t give a fuck if you think it isn’t better than ‘Stronger’. It also happens to be the best rock song so far this decade. Even Noel Gallagher loveeees it. When this song comes on in a nightclub I reverse engineer hundreds of thousands of years of evolution, beating my chest like an irascible ape that didn’t get his breakfast. The lyrics are hostile to everyone and everything, with allusions to royalty, howling wolves and King Kong. Only Phil Collins- ‘In The Air Tonight’ did a manic drum break better.

WINNER: Black Skinhead

Gold Digger v Gotta Have It

Of course I’m a fan, but ‘Gold Digger’ is overplayed to the point of karaoke status. Like Oasis’s ‘Wonderwall’, it is the go-to track for an artist who has many other superior hit singles. I hate predictable DJ’s. Nonetheless, I’m even less of a fan of Kanye and Jay-Z’s Watch The Throne, which reaped more rotten fruit than delicious apples of Eden. ‘Gold Digger’ was a moment where Kanye and pop culture were in perfect synchronicity. Fresh off playing Ray Charles in Oscar-winning biopic Ray, Jamie Foxx lent hook duties to Late Registration’s second single which sampled the soul legend (‘I Got A Woman’). After ‘Slow Jamz’ topped the Billboard 100 a year earlier, ‘Gold Digger’ ended up nabbing a second number-one single for the unlikely duo- I mean reallyyyy unlikely– of West & Foxx. I wonder if Kanye took his own advice on pre-nups.

WINNER: Gold Digger

Slow Jamz v No More Parties In L.A.

My brain is getting tired. ‘Slow Jamz’ is Kanye’s first-ever number one and it has the classic line: “She got a light-skinned friend look like Michael Jackson/Got a dark-skinned friend look like Michael Jackson”. But Kendrick Lamar is on ‘No More Parties In L.A.’ A Kendrick Lamar album produced entirely by Kanye West is my dream project. Where are those 40 Kanye & Kendrick songs? ‘Slow Jamz’ wins it… just.

WINNER: Slow Jamz

Say You Will v Good Morning

A great album opener should set the tone for the rest of the project. ‘Say You Will’ and ‘Good Morning’ achieve this in very different ways on 808’s and Graduation respectively. While ‘Say You Will’ is a fitting soundtrack to cold winter nights and saying goodbye to the world (if you’re that way inclined, you should probably ring the number on that Logic song), ‘Good Morning’ is the rise-and-sunshine alarm clock for fresh starts in paradise. Colourful and charismatic, like the Graduation cover indicates ‘Good Morning’ is the sound of Kanye shooting from the belly of the beast into a stratosphere reserved for superstars. I wish getting a degree was actually as fun as this animated music video.

WINNER: Good Morning

Power v Father Stretch My Hands, Pt. 1

The throne of Greatest Rapper Alive is a curiously ephemeral reign with a survival rate of precisely zero, sitting below a Sword of Damocles sharper than Chandler Bing’s wit. The love of hip-hop is an unrequited one that will cast aside its most Messianic figures at the first signs of failure. To be a rapper that permeates the public consciousness is to unveil your soul in the spotlight and still be misunderstood. Those who ascend to the mountaintop have no place else to reach but the heavens, futilely stretching their fingertips with the faintest grasp of divine status only to tumble to the base when they least expect it. For Kanye, that moment was the 2009 VMA Awards. Taylor Swift. We all know the one. Ever since, the impetuous gadfly that is Kanye West has been more discussed for his ‘rants’ than his art. As an aside, I don’t like the word rant. It implies someone not in control of their emotions or message. It should be used very sparingly. I detest imprecise language. Imprecise language leads to imprecise understanding, imprecise understanding leads to imprecise solutions, and imprecise solutions are undesirable ends in themselves. On ‘Power’, there is no imprecise language to speak of. The bigger the S on your chest, the more dangerous the kryptonite. 21st century schizoid man. King Crimson made it a hot line, Kanye made it a hot song. Illuminating the anatomy of dichotomy, Kanye asks us (and himself) a simple yet sobering question: you got the power to let power go?


Touch The Sky v The New Workout Plan

You can’t live life through a song quote, but if you could then for me it would be “any pessimists, I ain’t talk to them”. That’s exactly how I’m living life right now. It’s hilarious to me-and people that know me well come to think of it- that some people think I’m quiet. I’ve learned the hard way that most people are very insecure about honest, truthful expression, and I avoid them like they’re Charlie Puth songs. Before the day I die, I’ll touch the sky. If you don’t believe me get out of my life.

WINNER: Touch The Sky

Champion v Otis

Black excellence and prototypical Kanye production aside, I don’t have much to say about ‘Otis’. Jay is chillin’, Ye is chillin’, what more can I say?


Spaceship v Ultralight Beam

They both sound so soulful, don’t you agree? At the moment, ‘Spaceship’ is the Kanye song most relevant to my struggle, working 50 hours a week at a law firm in a job where I can’t utilise my talents, drowsily moonlighting as a dreamchaser against the quicksands of time. “I’ve been working this graveshift, and I ain’t made shit/I wish I could buy me a spaceship and fly past the sky”. I feel you Kanye. My spaceship is still in transit. Personal nexus notwithstanding, ‘Ultralight Beam’ is the narrow victor. Alongside Kendrick’s ‘Institutionalised’, it’s one of only two hip-hop songs to ever make me cry. Chance The Rapper’s verse could fill a church to the rafters with atheists. This is a God dream.

WINNER: Ultralight Beam

Diamonds from Sierra Leone v Dark Fantasy

Between 808’s and MBDTF, Kanye’s artistic metamorphosis was rivalled only by the upheaval of his life. Fame and money can’t stop a suicidal weakness. Kanye said so himself, concluding 808’s with a haunting, wailed freestyle (‘Pinocchio Story’) where he blamed himself for his mother’s death and pondered what it’s like to feel human: “There is no YSL that they could sell/To get my heart out of this hell/And my mind out of this jail”. That’s the Kanye you wouldn’t know about from your Facebook timeline. Back to the artistic metamorphosomethingorother. Two years later Kanye was done looking for Geppeto but not with childhood fables, drawing inspiration from Roald Dahl to paint the warped dreamscape of his ‘Dark Fantasy’. Even when balls deep in my overdraft, “how you say broke in Spanish? Me no hablo” remains a go-to Snapchat caption. Can we get much higher? I dunno. Roll another one and I’ll let you know.

WINNER: Dark Fantasy

Heard ‘Em Say v I Wonder

It’s far from my favourite, but damn is Late Registration classy. There’s still a CD of it somewhere at home. I’ll probably warm to it more as I grow older. Grown man hip-hop is hard to find in the age of Migos. ‘Heard Em Say’ is as lush as Michael Jackson’s falsetto, a Quincy Jones meets Gil Scott-Heron creation with a twinkling melody that could end civil wars. It also happens to have some of Kanye’s most poignant and insightful bars: “And I heard ’em say, nothing’s ever promised tomorrow today/From the Chi, like Tim it’s a harder way/So this is in the name of love like Robert say/Before you ask me to go get a job today/Can I at least get a raise on the minimum wage?” Suffering is part and parcel of life. Embrace that shit. Put your darkest secrets in a bottle, let it sail the high seas, strive and prosper.

WINNER: Heard ‘Em Say

Gorgeous v Homecoming

I suspect most people would pick ‘Homecoming’ here- even though the concept isn’t original– but verse two on ‘Gorgeous’ happens to be a frontrunner for my favourite Kanye verse: “Is hip-hop just a euphemism for a new religion?/The soul music of the slaves that the youth is missing”. One of the standouts on Kanye’s backhanded apology, Kanye & Kid Cudi are hip-hop’s Lennon & McCartney but with cooler outfits.

WINNER: Gorgeous

Family Business v Bound 2

Brooklyn, New York was the destination and 2013 was the year that I smoked my first joint. Bound 2 was playing. Winner. This is a pretty good time to segue into a Seth Rogen video…

WINNER: Bound 2

N****s in Paris v Late

Nobody knows what it means, but it’s provocative! It gets the people going!

WINNER: N****s in Paris

Round 2

Can’t Tell Me Nothing v So Appalled

Round 2. This is where things feat really interesting. And really tough. With the exception of this round, that is. It’s ‘Can’t Tell Me Nothing’ by a landslide.

WINNER: Can’t Tell Me Nothing

Hey Mama v Devil In A New Dress

I hope I have a son or daughter one day that’s as proud of me as Kanye is of Donda West.

WINNER: Hey Mama

New Slaves v Flashing Lights

Art references (“I’m just sayin’, hey Mona Lisa/Come home, you know you can’t roam without Caesar”), mischievous jibes at institutional ineptitude (“Feelin’ like Katrina with no FEMA”) and Chicago slang (what the hell is ol-wu-wopte?) coalesce on ‘Flashing Lights’, a cleanly-assembled futuristic banger. This would sound so good in a DeLorean.

WINNER: Flashing Lights

Love Lockdown v Through The Wire

If you really pay attention, you’ll notice how Kanye distorts his vocals on the lyric “Never know enough, ’til it’s over love/’Til we lose control, SYSTEM OVERLOAD”, and you might realise that’s why he gets paid the big bucks. It’s the little details that separate the trends from the transcendent.

WINNER: Love Lockdown

All Falls Down v Heartless

How many women do you know that went to college to get a degree in something they had no interest in only to end up doing hair or make-up for a living? I can’t count either. The opening verse on ‘All Falls Down’ has aged like Jennifer Lopez, elucidating on the pathway of the archetypal aimless female with stunning accuracy: “She has no idea what she doin’ in college/That major that she majored in don’t make no money/But she won’t drop out, her parents’ll look at her funny.” For every Steve Jobs or Mark Zuckerberg there’s a skyscraper full of college dropouts struggling to pay rent in a bedsit. In fact, college dropouts are 71% more likely to be unemployed. As Kanye puts it, however, many of our money problems come from overcompensation via mass consumption: “We’ll buy a lot of clothes but we don’t really need ’em/Things we buy to cover up what’s inside/’Cause they made us hate ourselves and love they wealth”. For a generation rewarded by narcissistic behaviour on Instagram, the need to redress the balance between ego and humility is more pressing than ever.

WINNER: All Falls Down

Highlights v Runaway

Not even close.

WINNER: Runaway

Blame Game v Good Life

Although Chris Rock’s hilarious outro on ‘Blame Game’ trumps any one moment on ‘Good Life’, I’m only ever taking in the 7:50 runtime when I’m strapping in for the full MBDTF experience. ‘Good Life’ is always a party favourite.

WINNER: Good Life

Get ‘Em High v All of the Lights

As he rightly said, if you’re a fan of Kanye you’re a fan of yourself. The genius in Kanye’s songwriting is that even when its ultra-personal he will find a way to open it up for the listener. Even when listening to a multi-millionaire with more Grammys on his mantelpiece than I’ve got birthday cards, I can feel our struggles are somehow linked. “If you want it you can get it for the rest of your life.” Time to get workin’…

WINNER: All of the Lights

Jesus Walks v Street Lights

But it’s hard to keep working when you know your worth and nobody else seems to see it, when all the work done behind-the-scenes reaps no dividends and your personal growth hits a dead end. You know your destination, but you’re just not there. You’re not in the moment nor are you in the fantasy in your mind. “Not yet”, you keep saying to yourself, “all in due time.” Consciousness is a strange and mysterious phenomenon that even the most perceptive of us can’t figure out, but we all know the bored, hazy panic that creeps in when we feel there’s no further knowledge to gain of who we are. On days like that we need a song like ‘Street Lights’. Even more than Jesus, apparently.

WINNER: Street Lights

30 Hours v Black Skinhead

It was iconoclastic, it was brash and for the blasphemy police it was difficult to stomach, but Yeezus lead single ‘Black Skinhead’ only reaching number 69 on the Billboard Hot 100 speaks volumes of the extent of Kanye’s fall from popular favour. Not to mention the uncompromising approach to the album itself. Not that I cared. As long as the music is good I’m happy. On ‘Black Skinhead’, Kanye crystallised what is obvious to anyone who follows music seriously; rappers are the new rockstars, and Kanye is the biggest of them all. Don’t take it from me…

WINNER: Black Skinhead

Gold Digger v Slow Jamz

Six of one and half a dozen of the other.

WINNER: Gold Digger

Good Morning v Power

I’ll let the lyrics speak for themselves: “I just needed time alone with my own thoughts/Got treasures in my mind but couldn’t open up my own vault/My childlike creativity, purity and honesty/Is honestly being crowded by these grown thoughts.”


Touch the Sky v Otis

OtisRedding>Curtis Mayfield. Kanye rapping over Otis Redding<Kanye rapping over Curtis Mayfield. “Before anybody wanted K. West beats/Me and my girl split the bucket at KFC” is a fast-food line of gourmet standards, the kind of rags-to-riches ethos that ravenous rap fans feast on for breakfast, lunch and dinner. Speaking of gourmet rhymers, and not for the last time Kanye would shine his light on a rose grown from concrete, ‘Touch the Sky’ also introduced the world to Lupe Fiasco. I always forget this song is produced by Just Blaze, who along with Kanye blazed a trail- pun intended- to beat-making stardom on Jay-Z’s most-revered album, The Blueprint. Amazingly, once upon a time Kanye was the guy you’d buy beats from when you couldn’t afford Just Blaze. Becoming an overnight sensation takes years of sacrifice. If nothing else, ‘Touch The Sky’ is one fine toast to success.

WINNER: Touch The Sky

Ultralight Beam v Dark Fantasy

If ‘Touch the Sky’ is Kanye ascending to the top of the world, ‘Ultralight Beam’ is looking down from beyond the heavens. I don’t know if there’s a higher power out there, but with music like this to bless my ears it’s impossible to rule out. Kanye’s greatest ever album opener.

WINNER: Ultralight Beam

Heard ‘Em Say v Gorgeous

Not easily separated. On another day, I’d opt for ‘Gorgeous’, but there’s something so intangibly special about ‘Heard ‘Em Say’ that goes some way to explaining why many fans miss the ‘old Kanye’ so much. Maybe it’s the track’s painful earnestness, maybe it’s the incisive social commentary, or maybe it’s Adam Levine’s porcelain hook; undeniably, ‘Heard ‘Em Say’ is a timeless assembly of low-key instrumentation that is greater than the sum of its parts. Where the black is darkest, the glow will shine brightest.

WINNER: Heard ‘Em Say

Bound 2 v N****s in Paris

It’s fitting that ‘N****s in Paris’ samples one of Will Ferrell’s many memorable movie lines, because like Step Brothers, Anchorman, The Other Guys and the many other hilarious Ferrell classics we’ve all been quoting for years (unless you’re a joyless weirdo), ‘N****s in Paris’ is jam-packed with t-shirt ready quotables. Jay & Ye are both on top form on Watch the Throne’s whimsical, flamboyant standout that is still accelerating decibel levels in nightclubs over five years after release. Automatic respect from me if you know all the words. I certainly do…

WINNER: N****s in Paris

Last 16

Can’t Tell Me Nothing v Hey Mama

‘Hey Mama’ is in my left ear calmly assuring me of the sentimental importance of familial bond, while ‘Can’t Tell Me Nothing’ is screaming over my right shoulder that I need to hurry up and get my finances in check so I can take charge of my own life. These are two very different songs, but ultimately it comes down to a simple question: what do I listen to more? Elderly wisdom is keen to remind us that we were given two ears and one mouth for a reason, but when you can talk your shit as well as Kanye, why listen to anyone but yourself?

WINNER: Can’t Tell Me Nothing

Flashing Lights v Love Lockdown

Tossing my Cultural Influence Hat to the side for just a second, I’ll have to do the dishonourable thing and totally forget that ‘Love Lockdown’ changed the sound of radio. Why? Because in spite of all that, for three minutes and fifty-seven seconds the pulsating, stuttering synths on ‘Flashing Lights’ will make you forget about all your complaints and grievances. This is the soundtrack we Get Out Our Dreams to. But hey, what do I know?

WINNER: Flashing Lights

All Falls Down v Runaway

Two perfect songs go to war. There isn’t a solitary moment on either of these tracks I don’t adore, both of them strong contenders to the Iron Throne of Kanye songs. Alas, only one can reign supreme over Westeros. As the emotional centrepiece of Kanye’s greatest album, ‘Runaway’ stands as Kanye’s most ambitious song at an epic nine minutes and eight seconds. We don’t hear a drum until almost fourth seconds in, and Kanye’s voice is absent from the piano-driven spectacle for the whole opening minute. ‘Runaway’ is total genius, connecting with seismic impact on multiple levels. On the surface… you know what- more on this later…

WINNER: Runaway

Good Life v All of The Lights

The more cerebral, esoteric and downright weird Kanye’s music gets, the more appreciative I am of his seemingly limitless creative capacity. However, not everybody is as nerdy as me, and with hit singles galore I can understand why the Kanye we hear on Graduation is the most likeable Kanye ever was. Who doesn’t want the ‘Good Life’? With Kanye looking happier than he has in donkeys, hopefully those Wyoming sessions can bring more joy to the world. Factor out the £500 phone and £30-a-month contract that you need for Spotify and Kanye is exactly right: the best things in life are free. You will need an extra tenner per month to avoid the God-awful advertisements though…

WINNER: Good Life

Street Lights v Black Skinhead

Probably the most polar-opposite songs in Kanye’s entire discography. If ‘Black Skinhead’ is akin to emerging from the shadows, bashing your chest triumphantly and snarling at your haters, ‘Street Lights’ is shutting the curtains, retreating into bed and reckoning with your scarred soul. Since there’s plenty of the former feeling to go around in Kanye’s music- although few of any do it as well as ‘Black Skinhead’- I’ll give ‘Street Lights’ the win. Overlooked and underplayed, ‘Street Lights’ says so much by saying so little, a tiny sliver of melancholic mystery that could draw tears to a glass eye.

WINNER: Street Lights

Gold Digger v Power

This time round, the emerging from the shadows, bashing your chest triumphantly and snarling at your haters song wins. The beat switch is fucking electric.


Touch the Sky v Ultralight Beam

Kanye is the master of suspense. For almost three minutes, the beat is barely there, drifting in and out, its total, spectral silence and intermittent injections of elevating soul the unlikely mise en scène companions. Probably what an actual “God dream” is like. And then the tour de force arrives. Chance The Rapper’s verse, perfectly paced and emotionally climactic as it is, remains among the best I’ve ever heard. “When they come for you, I will shield your name/I will field their questions, I will feel your pain/No one can judge/They don’t, they don’t know, they don’t know.” Is he talking about God or Kanye? I bet Dewey Cow listened to this before he introduced ‘Walk Hard’ to the world.

WINNER: Ultralight Beam

Heard ‘Em Say v N****s in Paris

If this were a custody battle, ‘N****s in Paris’ would be Adam Sandler. Yeah we’ve had some great times together and all that, and I’ve probably pissed up against a wall with you a few times, but it’s time to go. ‘Heard ‘Em Say’ on the other hand has absolutely nothing in common with my biological father, and that’s where this whole terrible analogy falls apart. I just realised how much I have in common with Sonny Koufax and it’s unsettling.

WINNER: Heard ‘Em Say


Can’t Tell Me Nothing v Flashing Lights

The two greatest songs on Graduation, but in what order? I just flipped a coin for this one. It really is that close.

WINNER: Can’t Tell Me Nothing

Runaway v Good Life

So, as I was spouting nonsense about earlier, ‘Runaway’ is total genius that connects on multiple levels. On the surface, it is a break-up song, where Kanye begins his verse by confessing his most repulsive character traits (“She found pictures in my email/I sent this bitch a picture of my dick/I don’t know what it is with females/But I’m not too good at that shit”) as a means to candidly convey the futile struggle of being a responsibility-shirking asshole. This ain’t the prose of William Wordsworth, nor should it be. No daffodil has ever made me that happy either, by the way. The pretentious among us will feign dismay at the horrifying thought that the profanity we all use on a daily basis could exist- God forbid- in song too. As an aside, Eminem put that debate best, calling out the colossal cognitive dissonance ingrained in taking kids to watch ultra-violent Arnold Schwarzenegger movies but getting your knickers in a twist over some lyrics (‘Who Knew’). Look deeper, and ‘Runaway’ is a tortured rumination on Kanye’s inherently problematic relationship with fame and the general public after the Taylor Swift incident (“And I always find, and I always find something wrong/You been putting up with my shit just way too long/I’m so gifted at finding what I don’t like the most/So I think it’s time for us to have a toast”). After what must’ve been months of self-reflection- not to mention his confrontations with suicide– Kanye reluctantly accepts that courting controversy is an inevitable by-product of his perpetually underwhelmed psyche.

WINNER: Runaway

Street Lights v Power

‘Street Lights’ has been the underdog story of the Kanye Madness competition, a song I am glad to have placed on the pedestal it deserves. Emerging top of the pile from a selection of entries that included ‘Stronger’, ‘Black Skinhead’ and ‘Jesus Walks’, ‘Street Lights’ is comparable to the Costa Rica of the 2014 World Cup, who ousted traditional heavyweights Italy and England (pints were had) as well as beating top seeds Uruguay on the way to a memorable last-eight finish. And then they met Brazil… and then ‘Street Lights’ met ‘Power’. It was lights out for the valiant Costa Ricans, and it’s lights out for ‘Street Lights’. Cue emotional montage. That’s the end of the trip. ‘Power’s’ voltage was just too much to handle. OK, that’s enough electricity puns- I’m guilty as charged…


Ultralight Beam v Heard ‘Em Say

This is the third album opener versus album opener tussle, and the most difficult to decide. With the legacy factor on its side, it’s difficult to deny ‘Heard ‘Em Say’. Now entering adolescent years, it still sounds as fantastic as ever. Will a 13-year-old ‘Ultralight Beam’ still knock the soul from my chest? I wouldn’t bet against it. In hindsight, its spectacular fusion of gospel and hip-hop served as a precursor to fellow Chicagoan Chance’s reverent, Rap Album of the Year-winning Coloring Book. Dubbed the official anthem for Christians who love to swear, you probably won’t need an ‘Ultralight Beam’ to trace the song’s impact by the time 2029 rolls round. For now, it’s just the best Kanye song of the past five years. Into the last four it goes…

WINNER: Ultralight Beam


Can’t Tell Me Nothing v Power

Here we are; the penultimate round, the Mount Rushmore of songs by Kanye West. It’s taken me about as long as Michaelangelo did to sculpt it. It was him, right? I really can’t believe I’m still writing this, and you wouldn’t believe how many cringeworthy metaphors, analogies and jokes I scrapped. Somehow, Michaelangelo survived the cull. Anyway, ‘Can’t Tell Me Nothing’ versus ‘Power’ would be a worthy final. As the most enjoyable Kanye song to rap along to, I’m going to give the nod to ‘Can’t Tell Me Nothing’. Ironically, though it is on ‘Power’ where Kanye raps that “every superhero needs his theme music”, it is ‘Can’t Tell Me Nothing’ that best fits the mantra. Appallingly, Graduation’s lead single failed to crack the top 100 in the U.K., although Complex later named it song of the decade. Many have tried to imitate Kanye’s iconic delivery here, but a song this pitch-perfect only comes around a handful of times a decade. Abundant with hilarious lines and an infectious hook that implores the listener to shut off all critics and shoot for the stars, ‘Can’t Tell Me Nothing’ is quintessential, feel-good Kanye at his very best. It doesn’t matter who you are, ‘Can’t Tell Me Nothing’ is your anthem. Whether basking in the glory of success with the windows down and the stereo up, or awaiting your time to shine as a penniless loser, the universal yet meaningful pop appeal of ‘Can’t Tell Me Nothing’ is tailor-made to bring a touch of style to the struggle.

WINNER: Can’t Tell Me Nothing

Runaway v Ultralight Beam

As much as I love ‘Ultralight Beam’, ultimately Kanye plays quite a minor role on his own song, more conductor-in-chief than lead performer. On ‘Runaway’ he plays both roles. Not only is it Kanye’s most emotional record, it also happens to have a vicious Pusha T cameo. His verse is directed at his ex and it stands so at odds with the elegant piano melody that it still blows my mind how such libidinous, shallow macho posturing (“Plenty hoes in the balla-nigga matrix/Invisibly set, the Rolex is faceless/I’m just young, rich and tasteless”) can be so simultaneously graceful that the ballet performance which accompanies the video feels like the perfect imagery rather than pretentious grandstanding. The answer? There’s a little bit of an asshole in us all, but that doesn’t make us any less deserving of empathy. The story goes that Kanye made Pusha redo his verse over and over, repeating the song’s mission statement: “I need more douchebag.” If Kanye’s lyrics are crude, Pusha’s are downright disgusting, as if Kanye needed an even more loathsome antagonist to realise lest he rein in his infinite impulses he was on the way to becoming Scarface. An overnight success may be years in the making, but destroying the whole house of cards takes only one solitary imprudent second.

WINNER: Runaway


Can’t Tell Me Nothing v Runaway

I’ma let me finish, but ‘Runaway’ is the best Kanye song of all-time! Of all-time! Why ‘Runaway’? In answering this question, I mostly thought of why I love Kanye, what makes him special, what makes his contribution to hip-hop unique. In a word, it is melody, so it’s only fitting that his most memorable melody of all takes top spot. If you give me two more words, it would be honesty and emotion, and ‘Runaway’ also has the honour of being Kanye’s saddest and most unabashedly truthful creation. Like no other before him, Kanye broadened hip-hop’s emotional and sonic palette, and his gift for melody brought this new form to the masses.

It is more than just a song. It is his beautiful, dark and twisted fantasy. ‘Runaway’ is Kanye on death row in the court of public opinion. Playing judge, jury and executioner, rather than exonerate himself he accepts full culpability. The vulnerability versus superficiality dynamic that underpins its philosophy speaks the ugly truth of the typical male experience. The only time a man will say he can’t relate to the lyric, “See, I could have me a good girl/And still be addicted to them hoodrats/And I just blame everything on you/At least you know that’s what I’m good at”, is when his wife is sitting on the adjacent sofa.

There’s not a single other artist in music that would’ve made ‘Runaway’ after Swiftgate. He gives zero fucks. Rightly or wrongly, artistic integrity is always Kanye’s prerogative. As Justin Bieber did with ‘Sorry’- a brilliant pop song but the most ridiculous apology pre-Kevin Spacey’s Twitter account– Kanye could’ve easily offered a contrived, insincere apology for his very public violations of moral orthodoxies, most damagingly at the VMA Awards. Thankfully, what we got is a portrait of the ugliest corridors of Kanye’s house of pain, framed with sorrow aplenty and just a light brush of contrition. The track, like Kanye, remains unresolved, with everyone but himself running away from who he is. Kanye West; be it the hubristic douchebag, the arrogant asshole, the obnoxious scumbag or the workaholic jerk-off, are all pieces of the whole, the meticulous auteur that can not and will not change. Caring too much can have some dastardly consequences. As for the muffled outro, what makes it so enchanting, so ethereal, so extraterrestrial? For once, I’ll let the music speak for itself.

WINNER: Runaway

Well, there goes several hours of my life I will never get back. Is it Yeezy season yet?