Drake's Top 25 Moments In Sports: Fair & Foul

Jesse Grant/WireImage
Lebron James and Drake attend the debut of 'The LeBrons' at Siren Studios on February 17, 2011 in Hollywood, California.

Drake may never have accompanied a championship-contending boxer to the ring, but as a Jewish-Canadian rapper, he sure knows about being an underdog.

Drake lives life like a guy who can walk again after being wheelchair-bound in high school. In an effort to make up for lost time and to achieve a certain level of cool, he befriends the most athletic guys, flirts with the sportiest girls, and because he technically can't win any sports trophies himself, he's giving them out tonight (Wednesday, July 16) as host of ESPN's ESPY Awards.

In honor of his sports standom, Billboard has pored through The Boy's entire career and found Drake's top 25 moments in sports - both fair and foul.

1. 1995: Drake enlists in hockey as a kid.
Unless Drake ends up repurposing a hockey video like his Bar Mitzvah one (for "Hell Yeah, Fucking Right"), then this does Drizzy no favors. Drake played for the Weston Red Wings as a child, and made it to the Upper Canada College hockey camp.

Verdict: Foul

2. February 2009: Chris Paul and LeBron James co-sign Drake, and blooms friendships.
Back when Drake was the future (as opposed to Future, the artist, and Future The Prince, Drake's DJ), he saw what a co-sign meant, even from fellow futures Chris Paul and LeBron James. A Chris Paul cameo on "So Far Gone" and LBJ coming through to the project's release party hold great weight and contributed to long-standing friendships between the three, who've gone on to become the president of the NBA Player's Association, the best basketball player on the planet, and a multi-Grammy Award winning superstar.

SO BEWARE OF A MIGOS-BOGDAN BOGDANOVIC-JOEL EMBIID TRIUMVIRATE, FOLKS!

Verdict: Fair

3. August 2010 - Drake reveals he once tore his ACL.
In 2010, Drake told ESPN.com, "I'm not going to lie, listen, I'm nice at basketball. The last game we played I dunked on someone, but I tore my ACL, so I haven't played in a long time." It's so easy to say you're "nice" at a sport, especially when your playing days were a long, long time ago; Al Bundy was nice at football, too. Maybe The Boy did kill everyone when he touched the court, but with no video footage, it's hard not to think that his story is just a legend that grows greater with time... or as some may say, legends start from the bottom.

Verdict: Foul

4. 2011-Present: Drake's courtside at all the NBA games (Toronto, Miami, L.A. Clippers)
There's no bigger measure of status in hip-hop these days than being courtside at an NBA game, if only to get on TV and remind ex-girlfriends what you look like in high-definition with your feet on the floorboards. Drake likes to switch it up too and appear at games in Los Angeles, Toronto, Miami, Brooklyn and others all in what seem to be the same night! Hi, Rihanna...

Verdict: Fair

5. July 2011: Drake throws opening pitch in 2011 Cleveland Indians Game.

Sipping from that double cup. The stumbling answer as to who his favorite team is. Not knowing where his own performance is taking place at ("On a closed off street somewhere. In a highly populated area.") Claiming right field in Little League. The capri pants. "I like baseball. Baseball's really good." The joke about the empty seats. A "pitcher's cage." Repeating what the interviewer says in his closing, like he's the guy's hypeman. The rainbow arc of the pitch: All of it no.

Verdict: Foul


6. August 2011: Drake attends a few of Serena Williams' matches.
After multi-time tennis champion Serena Williams broke things off with her rapper paramour Common in 2011, Drake jumped off the bench and grabbed his chance to be Lou Gehrig to Com's Wally Pipp. Drake hit her on Twitter with "@SerenaWilliams I can't wait to put it on you and make you sweat....... during our match this weekend."

He watched her play live; she did the same. But throughout the courtship, if you will, Serena claimed she and Drizzy were just "close friends." John McEnroe would argue about that one quite vociferously.

Verdict: Fair

7. October 2011: Drake features Toronto's SkyDome in the "Headlines" video.

Rappers are known to show off in their music videos by dropping the tops on their (rented) cars, and sometimes their (rented) girls. Drake upped the ante considerably by dropping the top of the Toronto Rogers Centre (lovingly still referred to as the SkyDome), home to Major League Baseball's Toronto Blue Jays, in the video for "Take Care" single, "Headlines."

Contrary to his love of sports, when it comes to his craft, Drake don't play. Later, Drake would work with MLB on an OVO x Blue Jays New Era fitted, just to stunt officially.

Verdict: Fair

8. January 2012: Drake performs at 2012 NHL All-Star Game.

If there's one rapper in the game that people have said can't dress himself, it's Jay Z. But if there was a second rapper with that same issue, people would nominate Drake. From Bill Cosby sweaters to batting gloves to his DaDa collection, it seems like he just can't get it right, but on NHL All-Star night in 2012, Drake certainly dressed the part. Thankfully he wasn't too cool for the arena - no furs, no sunglasses, and no skates. Wearing a working man's Timbs and a large hockey jersey with his name on the back, this Canadian national player shouted out Canada, the national sport, and the players in both his speech and his clothing.

Verdict: Fair

9. April 2012: Drake has multiple soccer allegiances.
Toronto police should ask Drake for his license and registration because he's double-parked a number of soccer bandwagons. Every social medium has evidence of him supporting a great number of clubs: he's a Manchester United fan. He's trained with Chelsea, hung out with Rio Ferdinand, spent time with Alex Oxlade-Chamberlain of Arsenal, and chilled with A.C. Milan's Mario Balotelli. The way he kicks it with each soccer franchise, no wonder people think his allegiances are relaxed.

Verdict: Foul

10. September 2012: John Calipari inspired Drake to finish high school.
Salute to Kentucky Wildcats basketball coach John Calipari, whose familial operation down there in the Bluegrass State provided inspiration to Drake, who'd dropped out of high school, to go back and finish his degree.

Now, it may not have helped any of Coach Cal's current crop of students as they weigh how far to go themselves in college, or any of his prior schools as a head coach, or even have anything to do with student athletes overall, but it's still cool that Cal (BREAKING NO NCAA RULES WHATSOEVER) paid it forward, so to speak.

Verdict: Fair

11. April 2013-present: His evergrowing friendship with Johnny Football.

Let's give credit where credit's due: Drake took Johnny Manziel under his owl's wing before the money, fame, drinking, partying, girls, cars, autograph controversy, ego, cell phone pictures, Justin Bieber, blow-up swans, using money as a cell phone, using girls as a cell phone, using liquor as a cell phone, being a TMZ staple, money, fame, drinking and partying, and has shown him unconditional family support.

If Johnny ends up with a long and fruitful career, he owes a great debt to Drizzy Drake. Related: somewhere, Tim Tebow fumes while drinking cranberry juice and refreshing his "Johnny Football" Google Alerts page.

Verdict: Fair


12. June 2013: Drake is rejected from the Miami Heat's locker room.

One of the best perks of being Drake is standing tall amongst champions - he's talked the talk and walked the walk in his art and business, so why wouldn't he be welcome in the athletic winner's circle? Why wouldn't Champagne Papi be able to pop some bottles with the 2013 NBA champs? Why won't they let Drake be Drake? Whatever the reasons are - rules, you know? - it comes off as awkwardly one-sided because of the cameras present. Unlike the Heat players, Drake got to witness the security guard celebrate publicly.

Verdict: Foul

13. June 2013: Drake goes clubbin' with LeBron James.
There's a whole bunch of reasons why Drake is overly-happy when he's in the club with LeBron: with LBJ likely the tallest person there, he'll never get lost; LBJ is never told no, even when he has a +35 for the guest list; LBJ understands Drake's moneytalk; and LBJ knows all the lyrics to every one of Drake's songs, which must be very flattering. (Drake probably doesn't know any of Bron's.)

But the biggest reason Drake it so happy is because LeBron's friendship is a rite of passage: he was Jay's friend first, then Kanye West's (remember 'Ye was with LBJ in Greenwich, CT for "The Decision") and now Drake's.

Also, LBJ's hairline is the perfect wingman for Drake's.

Verdict: Fair

14. September 2013: Drake becomes a pitchman for FIFA's video game.

I totally understand why Drake likes international soccer so much: the acting.

Verdict: Fair

15. September 2013: Drake becomes Raptors' Global Ambassador.

Jay Z owned a piece of the Nets. Usher owns part of the Cavs. Nelly owns part of the Hornets. But Drake's title is limited to "Global Ambassador?!" He's essentially Julia Louis-Dreyfus in "Veep," with a worse title. For all the good work he's done for the franchise and especially the city, the Raptors seriously need to let him buy into the team. Anything short of that, he should start abusing his authority. Some ideas, should he get to that point: daily press releases on Raptors stationary regarding Drake's lunch selection and booking random nights at the arena for giant games of manhunt.

Verdict: Foul

16. February 2014: Drake takes part in all 2014 NBA All-Star Weekend festivities.
At NBA All-Star Weekend you could either be a Diddy or a Kevin Hart. You could either be a Jay Z or a Kevin Hart. You could either be a 2 Chainz or a Kevin Hart. There's a certain effortlessness to be Diddy, Jay and 2 Chainz, sitting on the sidelines and letting people come to them. Kevin Hart, while a huge stand-up star and a box office sure-thing, still fiends for attention and will manifest that through celebrity games and having players jump over him in the dunk contest. Drake, don't be needy. Don't beg for attention. Don't bring your brand down a notch. Don't be a Kevin Hart. YOU'RE BETTER THAN THAT. YOU'RE BIGGER THAN THAT. YOU'RE TALLER THAN THAT.

Verdict: Foul

17. December 2013: Drake visits the Seattle Seahawks at their practice facility.
Drake visited the Seattle Seahawks this past December at their practice facility, after performing his tour in town. Not sure how I feel about this, being that Drake, as a FIFA video game spokesperson refers to soccer as football... sounds un-American to me. Oh, wait.

Well, however big of a football fan he is, why the Seahawks? Can't be because of proximity - that'd be the Buffalo Bills. Maybe because he's friends with Russell Wilson? Still though, the NFL wouldn't let him get away with being a bandwagon fan, like soccer apparently does. The only answer I can come up with is that he's doing this to spite Macklemore. And in that case... spite on!

Verdict: Foul

18. February 2014 - Present: Drake flirts with Skylar Diggins.

Clearly Drake likes to play basketball. He's definitely kicked a soccer ball around. He's thrown out a first pitch at a baseball game. He grew up playing on a hockey team. He's been spotted on the tennis courts. Drake's gone bowling. He's been involved in at least one confirmed ping pong match. But when it comes to flirting with girls who play sports: it's not a game with Drake. Take, for instance, Skylar Diggins, of the WNBA's Tulsa Shock. Drake has been quite clear in his infatuation with Skylar, posting three images of her to his Instagram, another of him wearing a Tulsa x Diggins tee shirt, and four videos of his best friend OB hilariously defending his honor. And all that was before Drake said of Skylar showing up to the ESPYs: "I've never met Skylar, but I’m sure it'll be extremely awkward if she does show up. She probably won't though… her boyfriend will probably have her tied down to a chair that night."

Verdict: Fair

19. April 2014: Drake hangs out in Kentucky Wildcats locker room after Final Four win.


I remember going to parties the summer before college, drinking with new friends, laughing with old friends, chasing girls, and living the life of a carefree teen. I remember coming back into town after freshman year of school, hitting similar summer parties and feeling on the outside of a lot of inside jokes I'd missed out on. I also remember visiting college for a big basketball game years after I'd graduated, and looking at these underclassmen, I felt hundreds of miles outside the inside jokes. Now add television cameras, millions and millions of viewers and multiply that by Drake.

Verdict: Foul

20: April 2014: Drake has "always" been a Wildcats fan.


What I love about this Vine is how Drake is all smiles to say what' up to some friend on the right of camera, and then the moment the cameraman/reporter opens his mouth, Drake turns sour.

Amazingly quick reactions and versatility: the same things that got Drake the gig hosting 'Saturday Night Live.' What I don't love is the proclamation that Drake has "always" loved Kentucky basketball. Here's what I want to hear: Did you think Billy Gillispie would be the best Kentucky coach ever, Drake? "Always." Does Jodie Meeks get to hang out with you at the club whenever he wants, Drake? "Always." Would you walk right past Ramon Harris or Mark Krebs or Matt Scherbenske on the street, Drake? "Always."

Verdict: Fair

21. April 2014: Drake takes a minute to roll off his lint courtside.


There are two main ways of thinking regarding the whole Lint Roller ordeal: 1. Who's paying such close attention to you as you watch the basketball game, that they'd see any lint that's clinging to your jeans? Or 2. You're a celebrity sitting courtside on national television, so don't do anything out of the ordinary that would catch unwanted attention!

Either way, it was a win for Drake. Before Game 5 of the NBA playoffs, the Toronto Raptors passed out 1,2000 Drake/OVO-branded lint rollers.

Verdict: Fair

22. May 2014 - Present: Drake supports Tyler Ennis, Andrew Wiggins and Anthony Bennett.

Amazingly, Toronto – the 416, or as it will become known on a worldwide level after the news of Drake's new album title, The 6 – has become a bigtime basketball city, which is fascinating considering the lack of success the hometown Raptors have had over the last decade. Studs like Andrew Wiggins, Tyler Ennis, Anthony Bennett and more have emerged from college as stars and are thrilling prospects as first and second year NBA players. And who is there, rooting them on and introducing them to a massive new audience via his Instagram account? Champagne Papi himself. And with this new crop of high-fliers, slashers and finishers, comes the popular new hand signal, the SZN – what Drake and his friends do to greet each other. Once again, it's the death of The Dynasty.

Verdict: Fair

23. June 2014: Drake attends the Astros game during Houston Appreciation Weekend.

When you think Drake, you think Toronto, Canada. If you're the US Government and you think Drake, you think of his home in Calabasis, California. If you're a high school senior basketball player and you think of Drake, you think of the great state of Kentucky. But if you're Drake and think of Drake, your mind immediately goes to Houston, Texas.

The adopted son of H-Town threw a weekend's worth of parties down in Houston in June 2014, and one of the bigger events was hosting an Astros game at their home stadium, Minute Maid Park. Drizzy, who has an Astros tattoo on his shoulder, showed the South how the North gets down in a custom Astros jersey, bringing kids to the ballpark, schmoozing with fans, and meeting with players before the game. In turn, the 'Stros showed Drake that they too get down, before winning in walk-off fashion, 5-4 over the Arizona Diamondbacks.

Verdict: Fair

24. July 2014: Nick Kyrgios picks a fight with Drake.
Where does one go after throwing shots at the likes of Kanye, Jay Z, Common, Chris Brown and Kendrick Lamar? Tennis, obviously. Nick Kyrgios felt that the entrance music (performed by Drake) played before one of his recent Wimbledon matches was too low-key, and ultimately cost him the first set. As Stereogum reported (via Sports Illustrated), Drake said, "I also want to meet this guy that says that he lost because he listened to my music. I also want to meet that guy and look him in the eye and see exactly who he is as a man and size him up and then chop him right down. Nick whatever-his-name-is — ’cause he didn’t win, so that’s how he’s going to be remembered: 'Nick whatever-his-name-is.'” No love lost in tennis.

Verdict: Foul

25. July 2014: Drake is looking into buying "real estate in Cleveland" because of LeBron and Johnny.
My AirBNB review of Drake's new property in Cleveland, which he'll rent out when he's not in town to support his great friends LeBron James and Johnny Manziel: Drake and the entire OVO were amazing - they were super friendly and accommodating, and went out of their way to make sure we (there were 4 of us) had everything we needed. The house was very clean and inviting, though the Rihanna-in-Browns jerseys FatHeads in each of the rooms might have been over the top. Laces out, Drake. 4/5 stars! Thank you for having us as guests!

Verdict: Fair