Drake, now more than ever, is at the top of his game. This past year, the Canadian rapper released an album, If You’re Reading This It’s Too Late and a mixtape, What A Time To Be Alive, along with rapper Future. Both releases have received overall positive reviews and reached number one on Canada’s Billboard. He’s effortlessly and unapologetically killed Philly-rapper Meek Mill‘s career (probably for good), and recently became a meme sensation after showing off his dance moves in “Hotline Bling”. But before hitting this pinnacle at this point in his career, Drake was known as quite the soft, singing and sensitive fellow.
He first appeared as humble Jimmy Brooks on the tween hit-show Degrassi, in 2001. But Drake certainly hasn’t let his rap career undermine his acting days. In his lyrics, Drake often alludes to his character Jimmy, claiming he’s still spending money from his acting career in his song “You Know, You Know”. But don’t overlook the ‘nerdy-Jimmy’ side of Drake. Women like a man with sensitivity, and Drake has proven to be quite the ladies man. His songs frequently insinuate that the rapper is blinded by old rendezvous and old-flames he can’t seem to let go off. Sometimes he sings, sometimes he raps, but here’s an idea as to who brings which side out of him:
10. Courtney From Peachtree
It’s not the first time that Drake mentioned a love-affair with a girl from Atlanta. In his song “From Time”, Drake stated the one he ‘needed’ to complete him was Courtney from Peachtree–the infamous Peachtree Hooter’s that is. The lyrics continued insinuating that they had life all planned out but those same plans were ended abruptly seeing that she apparently got engaged. We can’t help but wonder if this is the same ex that attended Georgia State in “HYFR”?
Drake isn’t afraid to admit his love for strippers. Featured as the love interest in the music video for “Find Your Love”, Maliah helped Drake find his love for her. Just like most of his boos, Drake couldn’t let this one get away without name-dropping the stripper in his song “Miss Me”. The flame went out quickly with her career choice being questioned for their breakup. In an interview on The Autumn Joi Live Show, Maliah claimed Drake was always a gentleman and always cared for her. Evidently, the breakup didn’t go as smoothly as planned because the two got into a Twitter spat afterwards:
There’s not enough Ben & Jerry’s in the world to heal Drake on this one.
8. Bria Myles
Although this relationship wasn’t as publicized as his past relationships, Drake still didn’t let that stop him from naming a song after Bria Myles titled: “Bria’s Interlude”. It must have been love, or lust, at first sight because in the song, Drake says:
I’m aware that we just met
I don’t wanna leave you yet
Promise that I won’t forget
I’m coming back, I’m coming back
Who knew you could fall in love in a short matter of time. Following the song, Drake mentioned her name yet again in his song “From Time” featuring Jhene Aiko, referencing to the place they met each other. In an interview with MTV, Drake said: “I was smitten over this girl from L.A. and I started writing a song about her.” Well, flames die as quickly as they ignite and people move on, just like Drake did.
Nobody saw this one coming, not even Drake. During their Coachella performance, Madonna stole a kiss and possibly even his soul as she seemingly suffocated him on stage. After having a 56-year-old woman kiss and suck the life out of me, I’d be quite traumatized. There is absolutely no way Drake walked away as the same person. He later said that he wasn’t disgusted by the kiss, but the look on his face afterwards said a lot different. It probably won’t be long before we hear a song with her name in it.
Before Chris Brown stampedes out of his bed and rants on Twitter, he can rest assured Drake never dated her. However, after the Drake and Chris Brown beef, Drake was a little uptight after rumors circled that Karrueche Tran and Drake hooked up. Not only did he clear the air, but shattered any crush she may have had on him by claiming Karreuche is not even his type. But his comments didn’t stop there. He referenced her in his song “Live From The Gutter” saying, “This for my dogs that go Karrueche with the chopsticks”. Although it could have double meanings, Drake used her name more than likely to shake Chris Brown up a bit–who is also known to be quite emotional.
5. Jade Lee
As we come down to number 6, we clearly see that Drake expresses his many affairs with women throughout his life through song lyrics. With this one, however, he got real personal with ex-gf Jade Lee, in “Karaoke”. Drake describes her as being a florist and the one he wanted to marry and moved to Atlanta. Years later, Jade and Drake reunited with Jade posting a picture captioned:”10 years ago we used to dream about being a rapper and an event planner”. Well, it looks like each of their dreams came true. Perhaps this is the woman who possibly inspired Drake to release the bitter ex-boyfriend’s anthem: “Marvin’s Room”?
4. Zineb Samir
Drake’s breakout single: “Best I Ever Had” catalyzed his ballads which he would seemingly soon treat like a diary. In “Best I Ever Had”, it is alleged that he is referring to ex-gf Zineb, who the song was dedicated to. Sources now say that his newest song “Hotline Bling” is dedicated to her, as well. Her Instagram pictures are said to have inspired the lyrics behind the hit song. Nonetheless, Drake confirmed his 2009 love for her in his song “Look What You’ve Done.”
3. Serena Williams
What started as a steamy exchange of flirtatious Tweets later transcended into the two having dinner and intimately celebrating Serena Williams’ win in Cincinnati. Back in 2011, Drake Tweeted: “I cannot wait to put it on you and make you sweat……….during our match this weekend.” Although it hasn’t been confirmed if the two are currently dating, Drake has shown his support for Serena by attending several matches. Even if the two don’t make it official, not scoring in tennis terms still means ‘love’!
Throughout his career, it’s been known that Drake has always had the hots for Bajan pop-star Rihanna. The two are said to have met at New York’s Lucky Strike Lanes & Lounge back in 2009. Just in time to alleviate Rihanna of the turmoil with ex-bf Chris Brown, Drake and Rihanna formed a sentimental bond. But apparently Rihanna did hurt Drake. In a 2011 interview with Elle magazine, Drake said:
“That was the first girl with any fame that paid me any mind. You spend days reading about this person in the magazines. All of a sudden you have this number-one song and you’re at some birthday party and there she is. And you’re just some naive kid from Toronto staying in some s—y-ass hotel who got invited to this party on a whim. That’s just how it happened.”
Since then, the two have been off and on which inspired Drake’s 2015 single: “Views From The 6”. In the song, Drake reminiscences on their past relationship and how they would act like a married couple. Now, Rihanna is rumored to be dating Travis Scott, but there’s no telling what the future holds.
1. Nicki Minaj
No other relationship epitomized “friend-zone” more awkwardly than Drake and rapper Nicki Minaj. Drake, on multiple occasions, has proudly proclaimed his love and infatuation for the rapper and business-woman. Though the two have publicly shared flirtatious chemistry with one another, nothing romantically ever spawned from them. In 2010, in his single “Up All Night” off his album Thank Me Later, he openly admitted that he loves Nicki Minaj and hoped they get married just to say they did it! His optimism didn’t stop there. On “Only” the rapper professed that he would be first in line when Nicki and then boyfriend Safaree’s relationship was over. Well, it looked like that went in one ear and out the other, because shortly after the release of the song, Meek Mill and Nicki Minaj began dating. On the bright side Drake, Nicki Minaj may be single soon if her beau keeps taking all these below-the-belt hits from other rappers.