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A2A: There are various factors to consider and this is a multi-faceted question that requires some deep-diving into Kanye’s psyche. The most important thing to consider is that West is constantly changing his musical tastes, so the best way to approach this question is to cut off a specific segment of time and try to get into his mind and think like Kanye would about what’s important to him. At present, Kanye’s evaluations of his work will undoubtedly be tinged with recency bias, as Kanye’s earnest belief is that his musical trajectory is one of constant progress. Needless to say, the public doesn’t necessarily agree with that evaluation.For the purposes of this question, I’m going to assume that at some point post-career, Kanye’s going to sit on a porch in Calabasas or Marina Del Rey somewhere, drink some Hennessy or lemonade and ask himself this very question. I must, of course, qualify this by saying that we’re assuming Kanye’s musical career ends following the release of The Life of Pablo, since we can’t know about any future projects.Without further ado: “Me Pretending I’m Kanye West Ranking His Own Albums if His Career Ended Today”9. Cold SummerYeah, no.Somewhat Notable tracks: “Mercy,” “New God Flow,” “Don’t Like Remix”8. Watch the ThroneI’m not going to make any claims about how Kanye feels about Jay Z or hint that this has anything to do with any existing personal antipathy he might feel for Jay.I will, however, advise that Mr. Carter’s relationships with his business associates tend to end on sour notes following their run (look to Roc-A-Fella for examples: Jaz-O, Amil, Beanie Sigel, Damon Dash, Kareem Burke, et al.). Given Carter’s recent tendency toward respectability politics and a seeming obsession with sliding into stuffier privileged circles, he’s generally distanced himself from Kanye and his reality T.V. family shenanigans of late. Does this extrapolate into sour feelings later in life? Who knows?Add to that possibility the fact that WTT was a side project that took on life following his recording sessions for My Beautiful Dark Twisted Fantasy — and that it robbed Kanye of his chance to win Album of the Year at the Grammy’s by dividing voters — and it’s a real case this might end up being Kanye’s least favorite album. MBDTF was a prohibitive favorite to win the AotY Grammy (it completely crushed year-end lists) but his early release of WTT in a way precluded due attention on the worthier effort.What sucks is that Watch the Throne actually spawned some great tracks. In the lens of Kanye, however, its gold Ricardo Tisci-designed cover might lose a little luster given its proximity to MBDTF.Notable Tracks: “No Church in the Wild,” “Otis,” “Paris,” “Who Gon’ Stop Me,” “Why I Love You.”7. GraduationThose who followed Kanye earlier in his career (eg. the Freshmen Adjustment mixtapes) know that a great deal of the material on Graduation was recycled lyrically and re-conceptualized under a different musical arrangement.Though just about everyone loves at least three or four tracks on the album, from a Kanye perspective, it was one of his most ephemeral efforts. The Takashi Murakami-commissioned Japanese cover art is now a gaudy mid-to-late-aughts signifier, and the lyrical references haven’t aged very well (why is there a song called “Barry Bonds” [and why does it suck]? Who is Kate Moss?).The interpolation of Daft Punk’s “Harder Better Faster Stronger” helped to usher EDM back into the U.S. mainstream music consciousness, but that might be the single most lasting impact of the album. And disagree if you like, but the numbers don’t lie: EDM itself is already dying.Notable Tracks: “Flashing Lights,” “I Wonder,” “Stronger,” “Homecoming”6. The Life of PabloRemember, we’re assuming his career ends on this album and this is twenty+ years down the road, and even then it’s likely Kanye doesn’t look back on this project as fondly as the next or previous ones on this list (in the West canon, I’d put it WAY behind Graduation). It’s the first time that West’s lyrical content seems a step behind the cutting edge of hip-hop, made stunning by the fact that “old Kanye” was the one so influential as to practically birth artists who are now his contemporaries.Still, West’s lyrical mission seems aligned behind what Kendrick Lamar is currently doing. Only now, the student Lamar completely surpasses West’s lyrical gifts and artistically impactful expressions of culture. West’s demeanor comes off like the slurred drawl of a disillusioned sybarite, whereas Lamar’s unique mix of passion and genius seems to drip from every couplet and internal rhyme.Make no mistake, TLOP was well-received, kind of like a early-days Cavaliers game where LeBron James puts up 30 points, 8 rebounds and 7 assists. Supreme talent coasting and mailing in a brilliant performance by a lesser individual’s standards. But the implacable feeling that West was losing his grip on the game to Kendrick Lamar was cemented in this effort. The album didn’t quite jibe like it must have in his head when he was making it, especially considering the album’s well-publicized foibles in utero and the piss-poor quality of lyrical content. By the way, who in the blue hell wrote these moronic nursery rhymes?“I bet me and Ray J would be friends… if we ain’t love the same bitch… ‘Ye mad he hit it first… Only problem is I’m rich (fades and echoes/pause for canned laughter).” Or that line about the t-shirt and the model.It’s shallow and asinine rhymes like these that make me long for 50 Cent rhyming “gun” with “fun.” As for this album? So done.Notable Tracks: “Famous,” “Freestyle 4,” “Ultralight Beam,” “No More Parties in L.A.”5. YeezusOf the album processes that showed a profound impact on Kanye’s life, I’d say Yeezus is perhaps the most seminal to his following work (unless we’re assuming West particularly enjoyed the use of AutoTune, in which case, well, you know which one was more seminal). What West termed “aspirational minimalism” was the result of Rick Rubin doing a last-minute stripping of elements that he might have made room for in previous albums.This establishes a couple things: (1) West was listening to critics who were complaining about the instrumental bloat in his tracks,and (2) Until Yeezus, it felt as if he didn’t quite know how to produce beats any other way.Sparse synth lines, industrial sounding guitar loops, and a crisp flow that sounds immensely polished resulted in an album that was a huge, challenging departure for hip hop fans to digest, and marked a further shift into West exploring themes of Afro-centrism.West ditches the lyrical nuance of his MBDTF efforts and plunges into the void, using snippets of emotion (like the primal scream in “I Am a God,” or the ferocity of a string of nursery rhymes about the Hamptons) and re-arranging and re-contextualizing them to make a much more poignant statement about what it means to be black, rich and famous in 2013 than he did in WTT. Would he consider it his best work? Well, from this point on, it’s actually up for debate.Notable Tracks: “New Slaves,” “Blood on the Leaves,” “Black Skinhead,” “On Sight.”4. Late RegistrationI can pinpoint the moment Kanye West became, in my eyes, a household name. It was when “Gold Digger” was enjoying a massive run atop the Billboard Hot 100 and the song was playing inside a sandwich shop. A lady looking at least 75 years old comes in, back hunched over, as “get off my lawn” as you could possibly look, and says in the most disapproving tone:“Kanye West {she pronounced it perfectly} totally ruined this great Ray Charles song.”Most Kanye fans will tell you that College Dropout was his Reasonable Doubt. If that analogy holds, LR was his Hard Knock Life, the moment that (along with “George Bush Doesn’t Care About Black People”) launched him into the public consciousness and made him a cause-célèbre forever and ever.What made LR so significant wasn’t just that we all loved it; it was that Kanye loved it more than all of us. He ran up on stage in defense of his album, went on ridiculous rants because of this album, and generally lost his mind about awards shows.The way Kanye reacted to the critical reception of Late Registration told us something: Somewhere, intrinsically, Kanye cares what all of us think. If what we think is not in line with what he thinks, it bothers the fuck out of him. It’s my theory that no matter how much he expresses otherwise in public at present, there’s still unsettled barbershop fodder rolling around in his head about the awards performances of his previous albums. Which is to say, Kanye isn’t necessarily an idiot savant trailblazer he paints himself to be; his musical style and his train of thought is at least partially reactionary in scope as long as those reactions pertain to something that was about him.The underrated part about Kanye’s newfound visibility was that it gave West the mainstream legitimacy and budgetary means to exploit his musical gifts and experiment with live instrumentation. Late Registration’s liner notes for musical contributors reads like a phone directory. It was West at his maximalist best; at least until c. 2010.Notable Tracks: “Hey Mama,” “Gold Digger,” “Heard ’Em Say,” “We Major,” “Diamonds from Sierra Leone,” “Gone,” “Roses,” “Drive Slow”3. 808s and HeartbreakBefore I start this explanation, I need every Kanye fan to put their guns and pitchforks down. I have this theory that every truly great, transcendent Kanye West album has come after a period of tremendous, excruciating personal hardship for him. Of course for 808s, it was the unexpected and sudden passing of his mother, which had a profound effect on him as an artist and as an individual.That said, there simply is no argument that 808s and Heartbreak was the second most influential album Kanye ever put out, aside from College Dropout. Why, you ask?Because this album gave birth to Drake. It made confessional rap more than just a one-off track for the ladies or a liquor spilling tribute to ones’ homies on every gangster rap record. It made it REALLY OK to be “soft” in rap. Most importantly, it humanized hip hop as an art form in the eyes of an America that too-commonly (and subtly in a racist way) associated it with a propaganda-like promotion of gang violence, drug-dealing, misogyny, homophobia and Uncle Kracker.For those of you who weren’t around for the hip hop Medieval era we call the ’90s, there were two ways you were going to sell rap records during that decade: act like a hardened misogynistic gangster archetype (preferably one who’s had his share of drug-dealing or potentially lethal experiences), or have the name “Marshall Mathers” or “Will Smith.” To be honest, that was about it, and no, we’re not counting “being signed to Rawkus” as “selling albums.”808s was a watershed moment for hip hop because it firmly marked the turning point away from gangster rap as the dominant form in hip hop. Auto-Tune gave Kanye free rein to start expressing hip hop lyrics musically, and the resultant album was sweeping, cinematic, futuristic and altogether gorgeous and musically tenable on its own legs, without relying on the tough-guy bravado and resplendent mafioso fantasies painted by his predecessors.It also had this effect: People who didn’t necessarily like rap were able to find something they liked about 808s because things like being in love with someone and wanting them to be faithful, or bemoaning how someone could “be so heartless” tend to resonate with, you know, everyone.Notable Tracks: “Love Lockdown,” “Heartless,” “Amazing,” “Paranoid,” “Street Lights”2. College DropoutOh, boy… I can already see the angry responses. If you’re reading this, you already know that a lot of the points I raised for 808s and Heartbreak are similar to the reasons why College Dropout was so significant. CD sowed the seeds for a shift away from the gangster aesthetic and proved, to at least record companies who wanted to make money, that confessional and socially conscious rap could sell even if your name wasn’t Mos Def or Talib Kweli.Going back to the point about tremendous difficulty spawning Kanye’s best work, I mean, forget the car accident for a second: The actual process of getting signed to a major label for Kanye was a massive shitshow delineated in painstaking detail in “Last Call.”And then the car accident: Without “Through the Wire,” the trajectory of Kanye’s entire career comes into question. Does he ever sow that seed that grows into this generation’s biggest cultural force, or ever get the opportunity to prove himself right? Does he ever get one of the choice spots on the Roc-A-Fella roster and get artistic license to work on Late Registration, Graduation, et al.? Does he have his preternatural fearlessness and the stomach-churning work ethic that comes after a near-death experience? Does his only major label rap contribution end up being that unforgivably shitty feature on Blueprint 2’s “The Bounce?”Even the visuals for the track were genre-bending, with little slice of life clips from around Chicago being framed into polaroid shots on a giant board. In 2003? This was some groundbreaking shit, people. The execs (cough, Dame and Jay) were going to have him rapping “Through the Wire” next to a pool surrounded by women, which would be the life equivalent of hosting your wedding reception at Chuck E. Cheese.And then you listen to the other tracks on the album: “All Falls Down,” “Slow Jamz,” “Jesus Walks,” “Never Let Me Down,” “Family Business,” and you realize, you know what? Maybe Kanye would have been alright anyway. But in Kanye’s mind, does all of this make it his favorite? Well, it depends. Do all artists look back on their earliest work fondly, or do they, like Kanye does, tend to think of their development as being a strict trajectory of evolution towards an abstract ideal?My Beautiful Dark Twisted FantasyOut of all the rap albums that usually get cited as being “the closest to perfection,” it’s usually Illmatic that gets the first nod. Nas’ virtually perfect LP sounded like an album rapped by someone who’d been waiting his entire life for the chance to spit bars on wax, like he had spent his entire life writing rhymes into his little notebook, was found by a super-collective of the world’s most talented beatmakers all bringing their absolute A-game, and the rest was just magic synergy.MBDTF is of that ilk. As time passes, even with Kendrick Lamar losing his shit on records and outrapping every wannabe contemporary back into a job at Target and tucking sensitive rappers back in their pajama clothes, MBDTF loses none of its luster, its timelessness a testament to how effectively it captured and refactored the soul of hip hop. This was an album that could have only been made by a person who was psychotic enough to try it, with the resources to do it, and the exposure and appropriate context for it to succeed. In short, it was an album that only one artist could have possibly even attempted with the hope of success. And like what has become West’s life story: Against all odds, it succeeded.I’d argue that the period following Taylorgate (or as I’d like to call it, “Kanye advertising his bedroom prowess prior to complimenting Beyonce”) was the most trying period of his life. His relationship with Amber Rose had ended (Making a stripper famous by the Clinton method as a coping mechanism to deal with your mother’s loss… and then being cheated on by said stripper, only for her to go chasing a shoddy flavor of the month artist, generally leads to an egomaniac bottoming out in life.)To add to these mounting losses, Kanye’s public persona was seemingly beyond repair. All but his most ardent fans (and even some of those) saw it as the end of Kanye West’s cultural relevance. And yet when we write him off is when his work seems to exert an amazing gravitational pull. Critics engaged in self-flagellation and garment-rending over its brilliance. We all lost our shit. I still get chills when I listen to GIl Scott-Heron’s voice on loop, asking “Who will survive in America? Who will survive in America? Who will survive in America?” If not Kanye, who, indeed?Notable Tracks: “Gorgeous,” “Power,” “All of the Lights,” “Runaway,” “So Appalled,” “Monster,” “Devil — actually you get the idea. There isn’t a single dud on this album. Which is why I strongly believe that, in retrospect, Kanye will look upon MBDTF as his most complete and flawless work. And for once, every goddamn person outside of Anthony Fantano would agree with him.