The Life of Pablo rapper may be one of the most decorated artists at the annual awards show -- he's been nominated every year since 2008, is tied for Jay Z for the most GRAMMY wins with 21, and among producers, trails only Quincy Jones -- but this year he's reportedly joining his friend, Frank Ocean, in boycotting music's biggest night.
"Kanye, it's probably going to be a question of -- if it will happen, it will or won't happen closer to the show," GRAMMY producer Ken Erlich told ET regarding the 39-year-old artist possibly skipping the show. "We've worked with Kanye many numbers of times ... Some of his greatest performances have been on the GRAMMYs. I would sure love to see him in the house."
So what gives? Well, much like with another one of Kanye's up-and-down friendships, there's some history.
2005: The College Breakout.
Kanye's first GRAMMYs were huge for the rapper, who won Best Rap Album for College Dropout, along with Best Song for "Jesus Walks," and a songwriting credit on Alicia Keys' "You Don't Know My Name," which won best R&B song.
Long before his Yeezus scowl, Kanye was absolutely beaming over his eight nominations, walking the red carpet with his now-late mother, Donda West.
2006: Ultra Travolta
But that "Famous" Kanye ego that we've come to know (and some of us, at least, love) reared it's head, when Kanye added three more GRAMMYs to his collection -- Best Rap Album for Late Registration, Best Rap Song for "Diamonds From Sierra Leone," and Best Rap Solo Performance for "Gold Digger" -- showing up in shades, and a tuxedo that he would later describe in his song, "Glory," as "ultra Travolta," and "a little guido."
... And the celebration continued to the G.O.O.D. Music after-party, where Kanye switched to an even bolder lavender suit, and puffed a cigar while holding a sign that read, "I TOLD YOU SO."
Kanye's been doing Kanye for a LONG time, is what we're saying.
2008-2009: Kanye the Performer
By this point, Kanye is a bona fide star, taking the stage with Daft Punk to perform his 2007 superjam, "Stronger," which heavily samples the DJ group, and trading in his sunnys for full-on light-up stunna shades.
Then in 2009, Kanye had maybe his quietest year yet -- which still included performing "Swagger Like Us" and "American Boy."
So wait.... when did the fallout happen?
Well, later that year was the Taylor Swift MTV Video Music Awards incident that lives in infamy, followed by....
2010-2014: The Yeezy Drought
The fallout from Kanye's mic-grabbing moment was real and legendary, leading many to write the rapper off -- until he released My Beautiful Dark Twisted Fantasy.
Considered by many to be his best work, the album earned Pitchfork's incredibly rare 10/10 score, and signified a turning point in Kanye's career from hip-hop hit maker to critically acclaimed music icon. But despite all that, one thing MBDTF didn't earn -- an Album of the Year nod in 2012.
The snub is rumored to be a major factor in Kanye skipping that year, the same year that his collaboration, Watch the Throne, with Jay Z -- who also skipped -- was also passed over for the show's highest honor.
Interestingly, Kanye took a pretty conciliatory outlook on the whole situation when he addressed fans about being overlooked during a Chicago concert.
"Everybody came to me last night like 'Congratulations,' 'cause you know I have the most Grammy nominations once again," Kanye said"But you know, people say, 'You ain’t have the Album of the Year or Record of the Year,' but I figured out though, that’s my fault, for dropping Watch the Throne and Dark Fantasy in the same year. I should’ve just spaced it out just a little bit more. But don’t worry, 'cause me and Hov gonna keep on making s**t."
Of course, during a 2014 concert in London, Kanye rallied against the show once again.
"People get on the phone with me and tell me, ‘What kind of business can you do, though? What type of business are you doing? What’s the numbers? How much did you sell? What’s the radio spins? How much shampoo can you sell with your face on it and s**t?'" Kanye said. "Since when was making art about getting rich? … Remind me again why we in this s**t? Remind me again why the GRAMMYs [can] suck my d**k.”
2015: "Beck" to His Old Ways...
Kanye turned up in 2015, only to nearly pull a repeat of his Taylor Swift moment when Beck beat out Beyonce for Album of the Year.
"The GRAMMYs, if they want real artists to keep coming back, they need to stop playing with us. We aren’t going to play with them no more," Kanye told E! after the show. "Beck needs to respect artistry, he should have given his award to Beyoncé."
Of course, after actually listening to Beck's album, and realizing it was "kinda good," the rapper did make good and apologize to the artist.
2016: The "Most Important Living Artist" Is Talking
Clearly, what this all shows is Kanye really does care about the GRAMMYs, and he confirmed as much in February 2016 when he went on one of his famous tweetstorms about the show.
"I think the Grammys are super important," Kanye tweeted. "I know so many cool artists whose hearts have been broken by the politics including mine ... We need to fix this."
"I feel the Grammy awarding system is way off and completely out of touch," he added. "Hi Grammys this is the most important living artist talking ... "If I'm not at the show next year then there is no show."
The rapper also broadened the scope of his attack, saying that he cares about changing the GRAMMYs for other artists as well, going so far as to bring up the issue of race.
"You like your black people a certain way also. You wouldn't have Future perform and that man owned the clubs last summer," Kanye tweeted. "All artists have a problem with it and I am going to fix it for us all starting right now."
"Neil [Portnow, Recording Academy head] please reach out as soon as possible so we can make the Grammys culturally relevant again," Kanye finished his thoughts. "We need to see Young Thug at the Grammys. Not just me and Jay in a suit."