[This article expands upon and updates a section of an article on Drake's relationship with basketball we ran in 2016.]

Drake's affiliation with the University of Kentucky basketball team is undeniably weird and easily explainable -- he is attracted to winners. By finagling his way into the UK inner circle, he gets to experience the life of an athlete. Being an athlete is about more than on-the-court excellence -- it is everything that comes with it, from the sweatsuits to the unconditional adoration of millions. Through years of hard work, Drake has surpassed Ashley Judd as the Wildcat's most famous supporter.


2010: Drizzy & DeMarcus

Drake cozies up to 6'11" DeMarcus Cousins during a postgame interview. The first of Drake's many "proud girlfriend moments."

2012-2013: Big rings

Kentucky gifts Drake a custom championship ring, engraved "Drizzy," commemorating their 2012 national championship. The next year, Drake returns the favor by narrating a documentary on the UK basketball program called "Bluegrass Kingdom: The Gospel of Kentucky Basketball."

2014 Final Four: Drizzy the motivator

Drake pays the squad a visit in the locker room to congratulate them in after their stunning 74-73 win in the national semifinal. He gives daps all around and delivers a quick pep talk to keep the players spirits high. "It's your story, it's your time!" he tells them.

But it didn't end well for the Wildcats, as they fell to Shabazz Napier and the UConn Huskies 60-54 in the national championship game. A forlorn Drake was in attendance to witness the defeat.

2014 Midnight Madness: The airball heard around the world

Wielding his trademark lint roller, Drake takes the floor with the team at Kentucky's 2014 "Big Blue Madness" kickoff showcase and participates in warmups. He hoisted dozens of jump shots, but history will only remember the air ball.

2015-16: Trouble in paradise

The day after Meek Mill accuses Drake of employing a ghostwriter on Twitter, the University of Kentucky serves Drake a cease-and-desist letter for taking a photo with recruit Charles Matthews during the aforementioned Big Blue Madness. Calipari insists it's no big deal.

But six months later Drake earns Kentucky another violation for taking a photo with UK point guard Tyler Ulis at a concert afterparty in Chicago. The 3-minute meet and greet constitutes "preferential treatment." Drake remains determined to rep Kentucky: one month after the second round of sanctions comes down, he is spotted rocking custom "Kentucky Blue" OVO Air Jordan 8s.

2017: A candid chat with Calipari

Drake hops on the phone with Calipari for a wide-ranging 55-minute discussion that ultimately lands on the Calipari's "Cal Cast" podcast. Drake discusses in depth his education, early acting experiences, and love of sports:

"What I love about sports is that there is a clear-cut winner. Because in music sometimes, it gets frustrating... In our sport of music, there is no clear-cut winner and it is all opinion-based. There is no score, there is no trophy to hoist at the end of the year. There's something about the competitor in me, it bothers me. But I love sports for that reason. It causes sorrow and pain, and it causes massive amounts of joy. That's why I gravitate towards sports, because I believe in my heart and in my mind that I'm a true competitor... when I want to get motivated, I have to turn on a Wildcats game." 

Where will Drake's infatuation with the University of Kentucky take him next?