In the last 15 years, has an artist used the medium of music videos as profoundly and as dynamically as Kanye West? At last night’s (August 30) 2015 MTV Video Music Awards, Mr. West received the honorary Michael Jackson Video Vanguard Award, placing him in the company of not only the award’s namesake, but in a 31-year gallery that includes The Beatles, Madonna, Beyonce, Guns N’ Roses, and LL Cool J.

Upon receiving the award from Taylor Swift, an emotional Kanye West left his first row seats, surrounded by wife Kim Kardashian, sister-in-laws Kourtney and Kylie, and longtime manager Don C. After more than one minute of crowd applause, ‘Ye reacted.

“First off, thank you Taylor [Swift] for being so gracious in giving me this award this evening,” began the artist who nearly six years ago, famously interrupted the Country-Pop sensation upon an award speech of her own. “I often think back to the first day I met you,” he said with a smirk. “I think about [it] when I’m in the grocery store with my daughter and I have a really great conversation about fresh juice—and at the end, [the people I talk to will] say, ‘You’re not really that bad, after all.'” He also admitted to being jeered by crowds of 60,000 at Major League Baseball games for the same reasons. He added that he often thinks back to September, 2009, “If I had to do it all again, what would I have I done?” After making jokes about his leathery fashion choice, and drinking half of a bottle of Hennessy (which he shared with the crowd), the father of one with another child on the way professed, “If I had a daughter at that time, would I have gone on stage and grabbed the mic from someone else’s?”

Looking at his image since that event, he publicly deduced, “After that night, the stage was gone, but the effect that it had on people remained.” That evening was in the midst of some of Kanye’s most tumultuous times. Less than a year removed from 808’s & Heartbreak (for which he was nominated but did not win), West was still mourning the late 2007 death of his mother, Dr. Donda West. After breaking up with five-plus-year girlfriend Alexis Phifer, the Def Jam/Roc-A-Fella Records star began a high-profile relationship with Amber Rose—his guest and companion that 2009 night. The grieving, wistful, and vulnerable artist of the late ’00s is a stark contrast, at least in album content, to that heard on his most recent Yeezus, the very name chanted by MTV show-goers. Perhaps in that night, Kanye went to the “angry” image he is given (and at times embraces) in dealings with media, paparazzi, and microphones, during his in-concert monologues that are regularly labeled with “rant” taxonomy.

Later in the speech, which took more than 13 minutes of live airtime, Kanye West acknowledged that networks, media, and the Internet have benefited from his polarizing image. He seemingly called out MTV for replaying the 2009 event repeatedly, as well for promoting the fact that Swift would be West’s presenter for the Vanguard award. The celebrity stated his ongoing opinion that conflicts with award shows, and deeming top creatives “losers” simply by not winning. He used Justin Timberlake and Gnarls Barkley works as examples, beyond his penchant for Beyonce’s “Single Ladies,” which propelled him to the podium six years prior.

Half a dozen years removed from one major televised event, West is 10 years to the week removed from another. On September 2, 2005, Kanye West went off-script for “A Concert For Hurricane Katrina Relief” to tell NBC viewers—and subsequently, many more, “George Bush doesn’t care about Black people.” While those sentiments ultimately prompted reaction from the then President of the United States, West publicly stated a controversial opinion that made impact. At a time when few were expressing anything but sympathy, Kanye West was a vessel for the anger many felt watching people lose their lives, their homes, and their histories on the government’s watch.

Perhaps speaking to his 2005 news-making statement, West continued, “Sometimes I feel I died for the artist opinion—I died for artists to have an opinion after they were successful.” Appearing publicly 10 years to the day after he released sophomore, Grammy Award-winning Late Registration, Kanye added, “I’m not no politician, bro.” The same words he stated at the top of his speech were repeated, “Listen to the kids, bro!” Referencing his music and celebrity, the veteran stated, “I will die for the art—for what I believe in. And the art won’t always be polite.” Admitting he had “rolled something up to take the edge off” earlier in the night, he offered advice to his creative peers, “Just worry how you feel at the time, man!” Later on, he would declare, “It’s about ideas, bro. New ideas—people who believe in truth.”

Discussing this era of change, perhaps something related to his diverse portfolio of visuals, Kanye then charged, “We not gonna teach low self-esteem and hate to our kids.” He urged that tomorrow’s youth will know how to stand up for themselves, as well as their beliefs. Applying that to his own family heritage, West touted, “If my grandfather was here right now, he would not let me back down.”

Perhaps with both President Bush, and West’s freedom of speech, and President Obama, who called ‘Ye “a jackass” following the 2009 bum-rush of the stage, Kanye West left people with an announcement that permeated the news streams into this morning, “And yes, as you could’ve probably guessed by this moment, in 2020, I have decided to run for President.”

At work on an album reportedly called SWISH, Kanye West’s next moves are a mere guess. 2015’s “FourFiveSeconds” seemingly bridged the gap from a tempered posture and a sheer emotional explosion. Last year’s “Only One” looked back at his mother, and looked at his family now, a loving link between Late Registration and 808’s, at least in content and theme. With an upcoming complete 808’s & Heartbreak concert at California’s outdoor Hollywood Bowl, his past and many shades are deeply relevant to his present.

Nine years ago today (August 31, 2006), Kanye West presented Hype Williams with the Michael Jackson Vanguard Video Award. A lot changed in the near-decade between Kanye West handing a trophy, and being handed one. In the video content alone, it has been a musical and music video run as strong as any. However, the mood, attitude, and gumption of the man behind the art appears to be coming to terms with some things, and hoping to better understand new ones.

Do you take Kanye’s politician ambitions seriously regarding 2020? Does this VMA speech affect your opinion of the man behind the music?

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