Someday, someone will write a best-selling book about Drake: From his rollercoaster relationship with Rihanna to his biggest career regret involving The Weeknd. Check out these stories and more in celebration of Drizzy's sixth studio album, "Certified Lover Boy."
Dropping Out of High School
Drake is one of the most seasoned figures in show business, earning $49 million last year alone. So you may be surprised to learn he was once a high school dropout. Yup, when Aubrey Drake Graham was just 15 years old, he left the Vaughan Road Academy in Toronto to pursue an acting career.
Ironically, the next few years would find him playing a high school basketball star known as Jimmy Brooks on the teen drama series "Degrassi: The Next Generation." Eventually, Drake graduated and earned his diploma. "As of tonight I have graduated high school!" he tweeted a few days before his 26th birthday.
Beginning as a Thirsty Blogger
Before Instagram and Twitter became the go-to way for artists to document their daily lives and interact with fans, blogging was all the rage. Circa the late 2000s and early 2010s, Drake and his manager Oliver El-Khatib, who's also the co-founder of OVO, operated a page on Blogspot. Looking back, the gems are endless.
From confessing his lust for a girl who ignored him despite having sent her a bouquet of flowers, from Vera Wang, to dishing on the "joy" and "pleasure" of lying down in his favorite bedsheets (a gift he received for Hannukah), Drake was as vulnerable on the OVO blog as he is on wax.
His Love Songs About Rihanna
Drake has made a career crooning about his romantic adventures and mysterious relationships. Yet when he recalled a steamy night at New York lounge Lucky Strike on "Fireworks" featuring Alicia Keys, fans quickly linked the lyrics to pop star Rihanna, as the two were seen making out there a few months prior.
Rihanna wasn't interested in a relationship at first, but the duo made great music together, including jams like "What's My Name?" and "Work." Then, at the 2016 VMAs, Drake claimed, "she's someone I've been in love with since I was 22 years old." They were every music fan's favorite power couple; sadly, they decided to go their separate ways.
Catching Feelings for Kylie Jenner?
Another one of Drizzy's most high profile relationships was with the one and only Kylie Jenner. While their connection was based on rumors, insider sources rumbled that "they seemed to be enjoying each other's company" at Drake's 33rd birthday party a few months after Kylie's split from another hip-hop tycoon, Travis Scott.
Talk around Drake and Kylie took a turn when an old song with Future leaked in which Drake calls Kylie a "side-piece" and says he's "got 20 Kylies." He also mentions Kylie's sister, Kendall. It didn't take long for The Boy to offer context on Instagram, writing, "Last thing I'd want to do is wake up having any friends of mine feeling disrespected."
Even Drake Can Get Curved
Actress Kat Dennings, most known for her role on the CBS sitcom "2 Broke Girls," once revealed on the talk show Chelsea Lately that she didn't follow-up with Drizzy after grabbing sushi with him, as she felt "overwhelmed" by his security outfit. A tweet about her appearance on Conan O'Brien also prompted Drake stans to attack her.
Speaking on his Twitter love, she said she earned "50,000 new followers out of nowhere," some of whom told her, "'F*** you, Kat Dennings' and 'You can't take Drake from me. He's mine.'" However, she was sure to add that Drizzy was "super, super nice" and a "lovely person." You think the Toronto native still has a shot with Kat?
What About His Half-Secret Family?
Where were you when you first learned of Drake's daddy status via his archenemy, Pusha T? His then-secret son Adonis Graham, whom he shares with former adult film actress Sophie Brussaux, was infamously introduced to the world on "The Story of Adidon" in May 2018. Still, not much is known about his blonde-haired baby.
There were rumors that Drake was considering unveiling Adonis in partnership with Adidas, though he later shot down that idea. He finally confirmed his existence on "Emotionless," rapping, "I wasn't hidin' my kid from the world / I was hidin' the world from my kid." Fans got their first look at the mini Six God earlier this year.
Raised by a Rock 'n' Roll Legend!
Drake's musical talent isn't an accident. His dad, Dennis Graham, is an accomplished musician himself. In fact, he was the drummer for Jerry Lee Lewis, who's often described as "rock 'n' roll's first great wild man." Residing in Memphis for much of his life, Dennis introduced Drake to live instruments and Southern culture.
At 65 years old, he hasn't seen anywhere near the fame and achievement his son has. But he's trying to launch a solo R&B career, dropping an album and a music video for "Kinda Crazy." Unfortunately, Drake and his pops have had some public disputes over Dennis's alleged lack of parenting during Drake's childhood.
One of His Biggest Career Regrets :(
Drake is undoubtedly the face of Toronto's music scene. Not long after his ascent to the top of the charts in the late 2000s, another name hailing from Toronto exploded onto the mainstream via a collection of moody, melodic mixtapes: The Weeknd. As two of the city's biggest faces, a homegrown partnership seems natural, right? Not exactly.
Yes, they worked closely to craft Drake's sophomore album "Take Care." But once those recording sessions wrapped up, they stopped talking to one another. In a tell-all interview with Rap Radar, Drake confessed, "My biggest regret would just be that [The Weeknd and I] didn't give people that album or tour." (Brb, crying.)
Feeling Like an Outsider as a Kid
Being raised by a white, Jewish mother from Canada and a Black, Catholic father with American roots, young Aubrey had a unique background. He attended a mostly white school in the wealthy suburb of Forest Hill, causing him to feel like somewhat of an outsider. "It was actually girls who gave me a harder time than guys," he once said.
As Drizzy's comfort in himself grew, though, he started to view being a Black Jew as a "cool twist" and something that makes him "unique." Plus, he considers Toronto a "true mosaic" when it comes to race, so he felt welcomed by the "open-minded" culture. Besides, how can you drag a smile like the one in his yearbook photo?
Drake Has a Secret Business
If you wait until the final few seconds of his quarantine-themed music video for "Toosie Slide," you'll see these words appear on the screen: Frozen Moments, LLC 2020. Fans know all about Drake's October's Very Own (OVO) business, but what the heck does "Frozen Moments" do?
Though it's been 10 years since the company was registered as an LLC in Florida and credited on Drake's breakout hit "Best I Ever Had," the answer is still murky. Trademarks for Drake-branded products are often filed via Frozen Moments. It also hunts down fake Drake-related websites. Keep an eye out for this name.
HBO and Netflix's Secret Weapon
HBO and Netflix have both identified Drizzy as somewhat of a secret weapon in recent years. Leveraging his "Degrassi" experience, Mr. Graham executive produced HBO's critically-acclaimed teen drama "Euphoria" starring Zendaya, as well as the reboot of Netflix's British series "Top Boy."
Similar to most things he does, success wasn't far behind. Both titles have garnered strong viewership since airing in 2019, leading them to be renewed for respective upcoming second seasons. Some critics have wondered aloud what Drake brings to the table as a producer; whatever it is, it's definitely working!
Floating Like Muhammad Ali. Sinking, Actually
Some would argue that Drake is on pace to be hip-hop's GOAT (greatest of all-time) when it's all said and done. He's already comparing himself to legendary entertainers, like the King of Pop. "I could dance like Michael Jack-son," he raps on "Toosie Slide." Apparently, he can box underwater like Muhammad Ali, too.
While treating Nike's Oregon headquarters like a playground alongside Lil Durk in the elaborate video for "Laugh Now Cry Later," there's a brief scene where Drizzy channels this famous photo of Ali throwing jabs in a pool. It's one of the few times the championship boxer wasn't trying to "float like a butterfly."
The Infamous Missing BlackBerry
"Understand, I could get money with my eyes closed / Lost some of my hottest verses down in Cabo / So if you find a Blackberry with the side scroll / Sell that motherf****r to any rapper that I know." These Drake bars from a 2009 remix of Kanye West's "Say What's Real" have taken on a life of their own.
Are the now 33-year-old's "hottest verses" still trapped within a discarded BlackBerry almost 11 years later? Did anyone ever find the phone in the back of a Mexican cab and sell it to a rapper in need? Has someone unknowingly made a hit thanks to one of Drizzy's lost raps? The world may never know.
Never Not Flying Private. Prepare for Take-Off!
When your job involves flying around the world for sold-out shows, you might as well travel with class. That's how Drake feels, at least. His $200 million Boeing 767 plane fittingly nicknamed "Air Drake "was reportedly given to him by Canadian airline Cargojet as part of a publicity play. Sheesh!
Inside the main cabin, the OVO team enjoys comfy leather couches and a huge flat-screen TV. Outside, Off-White founder and Louis Vuitton menswear artistic director Virgil Abloh is responsible for the eye-catching sky blue design. Oh, and whenever Drake departs, onlookers see this message on the bottom: "If You're Reading This We Left."
That Crazy Time He Barely Escaped a Robbery
2009 is one of the most memorable years of Drake's life. Not only did he release his Grammy-nominated mixtape "So Far Gone" but he was the victim of an armed robbery that resulted in a chain from Lil Wayne being snatched off his neck. He recalls the scary situation in the song "From Florida With Love."
He says, "Went and got a chain for me, I had to give it up / N****s had they pistols loaded pointed at my truck, aye / And you know that lesson stuck / From that day I never touched the road without a (Plugg)." The Boy later revealed that he thinks he was set up by the girl who he had taken out for a date that night in Toronto.
Did You Know? There's No Drake Without Lil Wayne
Most OVO fans are familiar with the relationship between Drake and his mentor Lil Wayne. Upon hearing his music through executive Jas Prince circa 2008, Weezy invited Drizzy down to Houston. The day they met, November 18, is forever immortalized in a track of the same name. But only recently has Drake expressed his true love for Wayne.
This past August, the Six God referred to him as the "most selfless artist ever" and claimed Wayne believed in him "after so many never called again." He continued, "Always pushed us forward every single night in people faces 20k packed into an arena and he had a whole set of his show dedicated to introducing us FOR YEARS."
His Top 5 Favorite Rappers May Surprise You
Critics often point to Drake's blending of rapping and singing as one of his greatest contributions to hip-hop. According to the man himself, 50 Cent and his song "21 Questions" motivated him to take his vocals to the next level, as 50 offered the "most inspiring example of a guy who's not supposed to be singing, singing."
However, 50 Cent isn't a part of Drake's "Top 5 Rappers" list, which was debuted earlier this year "since nobody asked." It includes The Notorious B.I.G., Lil Wayne, Toronto's Young Tony and Andre 3000. There's also JAY-Z, an idol of Drizzy's who has turned into one of his biggest rivals.
Always Protecting His Producer, 40
Noah "40" Shebib has been instrumental to Drake's success. Literally. After being forced to introduce himself to the Toronto artist by eventual OVO's El-Khatib, he emerged as Drizzy's go-to producer, crafting the beats behind many of his most well-known hits, from "Marvin's Room" to "One Dance."
Safe to say if someone messes with 40, they're messing with Drake, like when Pusha T called out 40's multiple sclerosis on his Drake diss track "The Story of Adidon." Drizzy decried "wishing death upon my friend" and threatened, "Someone’s gonna f*****g punch you in the f*****g face." Ding ding!
Skepta Had a Strong Influence on Drake
Skepta might just be one of Drake's favorite artists in the U.K. Apparently, he's the one who got Drake hooked on grime. So much so, that Drake often co-opts the flow and it made him passionate about the genre, long before he ever had a chance to fall in love with hiphop.
Drake tattooed the initials of Skepta’s label, Boy Better Know, right on his shoulder, so it kind of makes sense that Drake also gave Skepta his own song (an interlude, actually) on More Life for their first proper “collaboration.”
The Hot 100 is His Playground
Drake is the king of the Billboard Hot 100, having broken countless records on the popular music chart founded in 1958. Two of his most notable accolades: most Hot 100 entries among all artists ever (225) and the most top 10 hits of all-time (41). He once rapped, "I got more slaps than The Beatles," and he's not lying!
Given his dominance on the charts, it's no surprise he's made history at the Billboard Music Awards as well. In 2019, he won 12 awards, including Top Artist and Top Billboard 200 Album for "Scorpion," overtaking Taylor Swift as the show's leading award winner with 27 trophies total. Big numbers!
Grappling With The Almighty Grammys
The Grammy Awards have come under increased scrutiny from many members of the hip-hop community due to their mischaracterization of what's considered rap music. Back in 2017, Drake aired his frustrations with "Hotline Bling" winning Best Rap Song and Best Rap Performance, as he believes it's "not a rap song."
"The only category that they can manage to fit me in is in a rap category, maybe because I've rapped in the past or because I'm Black," he later said. Another big name who's called out The Grammys on this topic is Tyler, The Creator. To him, the term "urban" is "just a politically correct way to say the n-word."
Drake's Favorite Drake Album Is...
With so many timeless Drake projects, it's tough to say which one is the best. Could it be his melancholy sophomore offering "Take Care"? What about the strikingly confident "If You're Reading This It's Too Late"? You can't forget "Views" either. Turns out the man behind the art harbors a favorite title.
During his expansive interview with Rap Radar, Drizzy revealed that his favorite Drake album is "Nothing Was The Same." Premiered in 2013, Drake views his third studio release as "my most concise album." Yet his classic picks are a bit different and include "So Far Gone" and "Take Care."
About Those Tattoos of Aaliyah and His Uncle
If you've ever seen a snapshot of Drake without a shirt, you know his body is covered with tattoos of the faces of those people who inspire him. There's Lil Wayne, his Uncle Steve (who gave him the confidence to launch his music career), his loving grandmother Evelyn Sher, as well as the late R&B sensation Aaliyah.
The Boy reportedly got her likeness inked on his back in 2011, close to a decade after her passing in a Bahamas plane crash. Drake penned an open letter to Aaliyah, writing, "Not only was I one of your biggest fans but I was truly in love with you." He also promised to "make music in your honor until the day we finally meet."
Bouncing Between All Sorts of Hairstyles
Drake's hair has gone through many phases and each look can be linked to a stage in his career. When he was beginning as an actor he had a mini afro, a hairstyle that reappeared several years ago. Then, he went for a clean shape-up and added a line into his hairline in the mid-2010s, before opting to grow out his beard.
As a nod to his latest album, "Certified Lover Boy," Drizzy is turning into a total romantic, cutting a little heart into his hairline and giving fans a sneak peek on his Instagram Story. We knew that Drizzy wore his heart on his sleeve, but we had no clue he would end up wearing it on his head, too!
Learning Different Languages... And Using Them to Rap!
Growing up in Toronto, young Aubrey was exposed to myriad peoples with various cultural backgrounds, from Jamaicans to Middle Easterns. In fact, these influences have helped diversify and shape his sound. On "Only You Freestyle" featuring Headie One, Drake actually rhymes in Arabic.
"Habibti please, ana akeed, inti wa ana ahla," he raps. Translated, this line means, "My love, please, I'm certain you and I look better together." Elsewhere, his adopted Patois accent, which originates from Jamaica, can be heard on dancehall-style tracks like "Controlla" and "Twist & Turn."
Sleeping on Nearly $400,000. Zzzz
Countless amenities lie inside of Drake's 50,000 square-foot, $150 million Toronto mega-mansion nicknamed "The Embassy." Swanky indoor and outdoor pools; a two-story walk-in closet; an official NBA-size basketball court. But perhaps the most impressive of all is his nearly $400,000 mattress.
Well, $395,000 to be exact. Constructed by Swedish bed maker Hästens, one of the main materials in "Grand Vividus," as it's called by some, is horsehair. This kind of hair allows the mattress to breathe and conform more. Seen above in front of a champagne bar, the bed weighs roughly half a ton and took 600 hours to build. Sleep tight!
Kobe Bryant is One of His Favorite NBA Players
It's hard to find someone who isn't a fan of the late Kobe Bryant. Winning five championships and embodying a never say never attitude during his 20-year career with the Los Angeles Lakers, Kobe left a lasting impact on the world. One of the Black Mamba's biggest fans is Drake. Here's how we know.
Drizzy once wore a custom "Farewell Mamba" jacket as he watched Kobe play in his final All-Star game in 2016. Following the tragic passing of the NBA superstar, as well as his 12-year-old daughter Gianna, in a helicopter accident, Drake paid tribute by showing off Kobe's #8 and #24 Lakers jerseys in the "Toosie Slide" video.
Working With Nike on Something Massive
After rocking the Swoosh for ages, Drake finally partnered with Nike's Jordan Brand for several pairs of OVO-themed sneakers. His Jordan 12s have resold for thousands of dollars on sites like StockX. Yet these shoes are only the first step in what's turning into a full-fledged apparel partnership.
He's been working behind the scenes with Nike on a line of "Certified Lover Boy" merch, even though it was reported that he was denied the trademark for that name. Nevertheless, the Six God is unveiling a cap with a red lipstick stain on the brim, heart-stamped socks, a bomber jacket and more.
Repping the World Champion Toronto Raptors
It's only right that Drake is the global team ambassador for his hometown hoops team, the Toronto Raptors. Just like Drake, the Raptors "started from the bottom" and eventually won the NBA title over the Golden State Warriors in 2019 while led by Kawhi Leonard. Drizzy was in attendance, of course.
Not only does Drake rep the Raptors but the Raptors rep him whenever they can. They host an annual Drake night at Scotiabank Arena, have an OVO alternate uniform in rotation and practice at a facility called the OVO Athletic Centre that's sponsored by Drake and his brand. This man is basically a part of the team!
You Used to Be Able to Eat at Drake's Restaurant
To be honest, it feels like Drake has seen success in just about everything he's tried to do. From music to TV to sports to footwear. But there's one field that's proven extra challenging for the Six God to conquer: the restaurant business. He's opened and been forced to close two restaurants in downtown Toronto.
His first venture was called Frings, serving Asian fusion in a lounge-like setting. It shuttered in 2018 after a series of missteps, including customer walkouts and liquor license suspensions. Next was Pick 6ix, a sports bar that also suffered from bad press. In May 2019, a person was shot and killed outside hours after Drake left a party there. Yikes!