There appear to be few things Drake publicly loves doing as much as penning radio-ready ditties about his innermost feelings for his old flings, but being involved in sports, whether participating or as a spectator, has to be on the short list.

Lots of music heads also love sports, but when you're a huge fan who also happens to be the most viable rap artist on the planet, it gives you opportunities that the average Joe doesn’t get. And Drake takes full advantage of his influence and star power. The “Jumpman” rapper’s airtight relationship with his hometown Toronto Raptors is well documented, as well as his affinity for the University of Kentucky basketball program and their Hall of Fame coach John Calipari. But Aubrey’s sports fandom goes even further than just simply going hard for his favorite squad.

Courtside Drizzy has had a number of memorable documented moments while watching NBA games in-person (never forget his instantly meme'd lint roller or styrofoam cup confusion). He even directly affected game play during one matchup in the 2017-2018 season with his sideline antics. The OVO MC does not discriminate on athletics—whether spectating or playing the sport himself—and has even shown a love for pastimes outside of the big three, including tennis and ping pong. Most recently, he popped up at a Connor McGregor weigh-in to support the UFC star.

XXL looks back into the past and points out Drizzy’s biggest scores in the sports arena.

  • Drake Plays Serena Williams in Tennis

    August 2011

    Drake and arguably the greatest tennis player of all time, Serena Williams, played a bit of one-on-one. Drizzy actually bests the tennis champ in the video that surfaces online—he alludes to the friendly match on "Worst Behavior" when he raps, "I swear I could beat Serena when she playing with her left."

  • Drake Named Global Ambassador for Toronto Raptors

    September 2013
    Tom Szczerbowski, Getty Images
    Tom Szczerbowski, Getty Images

    Drizzy's hometown NBA team the Toronto Raptors bestowed the rapper with the position of global ambassador. In his role, Drake acts as a host, business partner and consultant for the team.

  • Drake Participates in 2014 NBA Slam Dunk Contest

    February 2014

    The 2014 NBA Slam Dunk Contest in New Orleans featured a number of antics. The Toronto Raptors' Terrence Ross used Drake as a prop for his dunk, as the rapper held the ball out for his high-flying slam. Ultimately, the Washington Wizards' John Wall took home the trophy.

  • Drake Celebrates With Kentucky Wildcats Following Final Four Win

    April 2014
  • Drake Hosts the 2014 ESPY Awards

    July 2014

    Drake was tapped to host the 2014 ESPY Awards. The rapper delivered a spot-on opening monologue showing his fandom and self awareness.

    "There are so many people here I respect. So many people I admire, that I would trade my life with," he jokes at one point in his opener. "I love all of you…until you start losing. Then you're dead to me."

  • Drake Plays Reggie Miller in Ping Pong

    February 2014

    After some smack talk, Drake and NBA legend Reggie Miller squared off in a game of ping pong during NBA All-Star Weekend in Toronto. After a valiant effort by the 6ix God, Miller came out victorious.

  • Drake Helps Cause Turnover During NBA Game

    March 2016

    Drake can regularly be seen sitting courtside at Toronto Raptors games. During a match up in 2016 against the Chicago Bulls, Aubrey appeared to make enough of a distraction to cause a Bulls player turn the ball over during an inbound play.

  • Drake Plays Faceketball With Jimmy Fallon

    May 2016

    Drake is even down to try out new sports. In May 2016, he appeared on The Tonight Show Starring Jimmy Fallon and got down with a game of faceketball, which is exactly what it sounds like. He and the host wore backboards and hoops on their foreheads while dunking and shooting on the opponent's rim.

  • Drake Hits Half Court Shot While Lying Down

    August 2016
  • Drake Gets Into Altercation With the Cleveland Cavaliers' Kendrick Perkins

    May 2018

    Drake's fandom almost got him into a fight with the Cleveland Cavaliers' Kendrick Perkins during Game 1 of a playoff contest between the Cavs and Toronto Raptors. The two exchanged heated words during the game; later, Drake was warned by the NBA for using foul language.

  • Drake Supports Demar DeRozan Following Trade From Raptors

    July 2018
    Todd Korol, Getty Images
    Todd Korol, Getty Images

    The Raptors traded the face of their franchise, Demar Derozan, over the summer. The NBA star revealed that Drake was one of the people who helped him get through his rough patch.

    "The day it came out, I went to Drake's house," DeRozan tells ESPN's Chris Haynes. "Sat and talked for a couple hours, man. Not even on the hoops stuff, just my partner. Just to hear the words that come from him being the person that he is in this world, especially in Toronto. What I meant to the city—it was what I needed."

  • Drake Backs Conor McGregor at UFC 229 Weigh-In

    October 2018

    If Drake is with you, he is all the way with you. In preparation for Conor McGregor's fight in UFC 229, the Toronto artist showed up to the weigh-in with an Irish flag draped over his shoulders—a show of support for McGregor.

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