Drake’s Toronto

An interactive guide to the mogul’s hometown

No musicians tell the stories of their cities quite like rappers do. The way Jay-Z navigates the streets of Brooklyn, how Nas gives us a view from his window out onto the New York City neighbourhood of Queensbridge, how you feel like you’re in the passenger seat driving around Long Beach, Calif., with Snoop Dogg, or how Outkast takes us directly to East Point in Atlanta — the music of these artists transplants the listener to another time and place.

This is what Drake does for Toronto — whether he’s running through the 6ix with his woes, driving on the 401 and taking the Markham Road exit to Scarborough, or reminiscing about his time growing up on Weston Road. Through his music, Drake helped put Toronto on the map, so it seemed appropriate to map out Drake’s Toronto.

Illustration: Line Art Ben Shannon / Montage Andrew McManus

Early Years


Before Drake was a world-dominating music star, he was a young kid making his way through creative circles in Toronto, acting on Degrassi and releasing buzzy mixtapes such as Room for Improvement, on which he confidently claimed: “City is mine.” Little did everyone know how right he was.


Young People’s Theatre

165 Front St. E.

Drake’s mom, Sandi Graham, enrolled him in Young People’s Theatre as a kid. He was involved in a production of Les Miserables, which arguably sparked his love of acting.


Epitome Pictures (now closed)

220 Bartley Dr.

At the age of 14, Drake was hired to play Jimmy Brooks in the original cast of Degrassi: The Next Generation. The majority of the show was shot at Epitome Pictures, but some of it was also shot on location on De Grassi Street in the city’s east end. Drake went on to appear in 145 episodes of the series. In 2007, in an episode titled “It’s Tricky,” Drake raps for the first time on the show, performing a song called Tell Me Lies.” In 2009, Drake left Degrassi, claiming in a 2015 W Magazine interview that he was “kicked off the show” due to his burgeoning music career, which took up more and more of his time.

EARLY 2000s

Forest Hill Collegiate Institute

730 Eglinton Ave. W.

Drake attended Forest Hill Collegiate before he transferred to Vaughan Road Academy. He later dropped out of school to continue acting on Degrassi. “I never really got, like, a great school experience,” he said in a 2012 interview with Kentucky Sports Television

2003, 2004

The Avocado Supper Club (now closed)

257 Adelaide St. W.

Drake would perform here as part of a cover group called the Renaissance, which also featured Melanie Fiona and Voyce, a.k.a. Aion Clarke. As recounted in the book Far from Over by Dalton Higgins, Drake was eventually fired from the group and told by the manager, “I don’t think music is your calling.” The group permanently broke up shortly after that. Fiona went on to win a Grammy and Clarke has written songs for Drake, Rihanna, Diddy, Monica, Stormzy, Ed Sheeran and more.

NOV. 14, 2007

Phoenix Concert Theatre

410 Sherbourne St.

One of Drake’s first ever live performances was at the Phoenix Concert Theatre, where he opened for New York rapper Mos Def. Toronto artist Richie Sosa joined him onstage. According to the online blog HipHopCanada, the audience wasn’t very receptive to his set: “Faces stayed screwed.”

Noah (40) Shebib


Producer and songwriter Noah Shebib, a.k.a. 40, is one of three primary directors of OVO — Drake's brand, which stands for October's Very Own — and Drake’s musical right-hand man. He is the sonic architect behind the downtempo, dark, cinematic sound that is the rapper’s musical trademark. As Drake’s recording and mixing engineer for the So Far Gone sessions, 40 saw how frustrated his friend was getting as Drake tried to find the right sound through other producers. He turned to their mutual love of ’90s R&B and produced what he thought Drake was looking for — and it worked. Since So Far Gone, 40 has produced tracks and served as executive producer on all of Drake’s albums, rarely producing for other artists. Even the songs 40 has produced for other artists — such as Jamie Foxx, Alicia Keys and Lil Wayne — have been co-written by or began as songs originally intended for Drake. He is also considered one of Drake’s closest friends.

Illustration: Line Art Ben Shannon / Montage Andrew McManus

Jane Street and Weston Road

And it's a trip, my city broke into sections/ up north I got me a couple of troubles, couple connections.

City is Mine / Room for Improvement

Photo: Robyn Beck / Getty Images


Yo, the city is mine (which one?) T-O-R-O-N-T-O

City is Mine / Room for Improvement

Photo: Robyn Beck / Getty Images

Entertainment District

I’m from the city where people be gettin’ lazy/ litterin’ in the streets/ and the club district is poppin' like literally every week.

Make Things Right / Room For Improvement

Photo: Robyn Beck / Getty Images

Exhibition Place

Instead of saving for marriage, she saving for Caribana.

Come Winter / Room for Improvement

Photo: Robyn Beck / Getty Images

Future the Prince


Adel Nur, also known as Future the Prince, is one of the brains behind the business side of Drake’s OVO empire. “Future took the business and ran it for me,” Drake raps on Nonstop.” Future began working with Drake as his tour DJ and has since become his manager, as well as one of the architects behind OVO Fest and the lead on Drake's partnerships with Apple, LeBron James' production company Uninterrupted and entertainment company A24. Nur is also co-executive producer on the HBO series Euphoria and the Netflix reboot of Top Boy. You can also often see him sitting courtside with Drake at the Raptors’ hometown games. 

Illustration: Line Art Ben Shannon / Montage Andrew McManus

So Far Gone


Through the release of the well-received mixtapes Room for Improvement (2006) and Comeback Season (2007), Drake managed to catch the attention of Houston’s Jas Prince, son of Rap-A-Lot mogul J Prince, who then put Lil Wayne onto the young Toronto rapper/singer. By the time his third mixtape, So Far Gone, was released, with its hit single “Best I Ever Had,” it was clear that Drake’s star was on the rise, with no sign of coming down soon.

JAN. 15, 2009

Scotiabank Arena

40 Bay St.

When Lil Wayne made a stop in Toronto for his I Am Music tour, he brought out Drake to perform verses on their collaborations “Mrs. Officer” and “Pop Bottles.” It was a defining moment for Drake, proving to the hometown crowd that he could go toe to toe with one of the top rappers in the game.


6 Degrees

2335 Yonge St.

Drake celebrated the release of his mixtape So Far Gone with a party in Toronto, attended by none other than NBA star LeBron James. “A decade ago, you came to my release party at 6 Degrees and made me the biggest artist in the city off your presence alone,” Drake wrote on Instagram in a post celebrating the mixtape’s 10-year anniversary. The party, and James’s appearance, showcased Drake’s ability to transcend Toronto fame, and marked a special moment in Drake’s rise to the top — not just as a rapper, but as a cultural figure. The two remain close friends.

MAY 2009

College and Beatrice

College and Beatrice streets

With more fame comes more problems, even at an early stage. Outside of a restaurant in Toronto’s Little Italy neighbourhood, Drake was mugged at gunpoint. “I feel like in Toronto — from a rap standpoint, or even from being a young, black kid — I’m the only one to achieve this level of success,” Drake told Maclean’s magazine in 2010. “Those individuals who hate to see a person succeed, those are the individuals I fear, because in this city I would be their No. 1 target.” He also told GQ he thought the incident was a setup. The rapper lost around $4,000 and a new chain that Lil Wayne had given him. “I knew it was a setup, because I had on a sweater and a jacket. But when they banged on the car window with a gun and opened the door, the first thing he said was, ‘Yo, run that chain.’ They didn’t rob [my date], and her purse was sitting right there. So I was like, ‘OK, yup — you set the whole thing up.’”

MAY 13, 2009

The Sound Academy

176 Cherry St.

Drake’s performance at the Sound Academy (now called Rebel) marked his first sold-out concert to a hometown crowd. It was just prior to Drake signing to Lil Wayne’s Young Money label, but the buzz was already very real, with the audience singing along and finishing the lyrics to his songs. At one point, he made a specific appeal to the women in the audience, saying, “I need a Toronto woman. I know how hard Toronto women work to look good and smell good and get their money. … I want you to come home to me [and] I want to have a meal ready for you, like some roasted chicken breast or some steak frites. Maybe like a glass of wine, like some pinot grigio or some moscato.”

OCT. 1, 2009

Successful video shoot

Near the Rogers Centre

Drake teamed up with Trey Songz for the hit single “Successful.” The music video for the song was shot in Toronto, with Drake performing on the balcony of a building with the lit-up outline of the Rogers Centre glowing just behind him. It was the first of many music videos to feature Toronto references. 

Matthew (Boi-1da) Samuels


The Jamaica-born, Toronto-raised Matthew Samuels, also known as Boi-1da, is a 14-time Grammy-nominated record producer. In 2019 alone, he was behind three of the five best rap song Grammy nominees, and was nominated for producer of the year. Boi-1da has been making beats since he was 15, and was introduced to Drake after winning the Battle of the Beat Makers contest three times. Boi-1da worked on three tracks for Drake’s first official mixtape, Room for Improvement, and went on to produce dozens of tracks for Drake, including his breakthrough hit “Best I Ever Had,” as well as “Headlines,” “Forever” and Rihanna’s “Work.” He’s also the executive producer for Drake's 2015 mixtape album If You're Reading This It's Too Late

Illustration: Line Art Ben Shannon / Montage Andrew McManus

Thank Me Later


Drake’s debut studio album, Thank Me Later, was one of the most anticipated releases from a young artist in 2010. Featuring guest appearances from the likes of Lil Wayne, Jay-Z and Alicia Keys, plus production by some of the best in the game (including Kanye West, Timbaland, Swizz Beatz and No I.D.), the album also saw Drake solidifying his Toronto crew; the majority of the production was handled by longtime collaborators 40 and Boi-1da.

AUG. 1, 2010

OVO Fest

909 Lake Shore Blvd. W.

Drake hosted the inaugural OVO Fest at the Budweiser Stage, formerly named the Molson Amphitheatre. The one-day event, which expanded to two days in subsequent years, was notable for featuring an impressive cast of surprise appearances by Jay-Z, Eminem, Rick Ross, Young Jeezy, Bun B, Fabolous, Mack Maine and Kardinal Offishall. Star-studded cameos went on to become a regular occurrence at every OVO Fest that followed, featuring performers like Diddy, Mase and Stevie Wonder, making it a must-see event every August long weekend. But as with many events that are in high-demand, OVO Fest ticket prices have skyrocketed each year due to resale and scalping inflations. In 2019, tickets were being sold for $2,500. In an Instagram comment, Drake told a fan: “I can control a lot of things but I can't control resale prices shordeeee.”

College and Beatrice streets

Which made me question when I went missing/ and when I started treating my friends different/ maybe it was the fast-paced switch-up/ or the two guns in my face during the stick-up/ maybe 'cause a girl I thought I trusted/ was who set the whole shit up.

The Resistance / Thank Me Later

Photo: Theo Wargo / Getty Images

1 St. Thomas St.

These are my 1 St. Thomas flows.

9AM in Dallas / Thank Me Later

Photo: Theo Wargo / Getty Images

Oliver El-Khatib


If Future runs the business of OVO, then Oliver El-Khatib runs the brand. “I let Ollie take the owl, told him brand it for me,” Drake raps on “Nonstop.” El-Khatib is the person behind the October's Very Own moniker, named after the birthday month he shares with Drake. The two met when El-Khatib was managing the tastemaker clothing boutique Lounge. He’s also credited with bringing the Weeknd to Drake’s attention and signing PartyNextDoor to OVO Sound. El-Khatib also oversees the OVO clothing line, including partnerships with Roots and Canada Goose, and a Drake sneaker deal with the Jordan brand. Their relentless work ethic has fuelled Drake’s success as a musical artist and beyond: The OVO clothing line was estimated to top $50 million US in revenue in 2018 alone.

Illustration: Line Art Ben Shannon / Montage Andrew McManus

Take Care


More than any other album, Take Care cemented Drake’s Toronto sound. Co-executive produced by 40, the album presents a moody blend of rap and R&B, subterranean minor keys and existential themes. It also marks the first major collaboration between Drake and the Weeknd, who co-wrote five of the 18 songs on the album. Take Care debuted at No. 1 and won for best rap album at the 2013 Grammys.

MARCH 27, 2011

Scotiabank Arena

40 Bay St.

After scoring two Juno Awards in 2010, Drake hosted the 2011 ceremony in Toronto. While he was widely praised for his hosting and was nominated for six awards for his breakout album, Thank Me Later, he went home empty-handed. That marked the first time in the Junos' 40-year history that a musician host didn’t win a single award. Drake won four Junos in subsequent years, but stopped submitting his music for consideration after 2016’s Views. In 2019, president and CEO of the Canadian Academy of Recording Arts, Allan Reid, told CBC: “It’s unfortunate he chose not to submit, and hopefully, he will come back.”

JULY 31, 2011

OVO brand launch

909 Lake Shore Blvd. W.

The OVO clothing label launched with an announcement on the OVO blog in summer 2011. Photos of limited edition merchandise, including a special tour jacket in collaboration with Roots, were made available with a note that it would all be for sale at the 2011 OVO Fest.

“I want people to be a part of our movement, I just want it to be right,” Drake told Complex in 2011 of the burgeoning clothing brand. “And everybody else wants me to make it with the cheaper fabric and put it in Macy’s and ‘Oh, don't worry, we will make $100 million in the first year.’ Naw, f--k you, because that's not what we are about.” The first official OVO store opened three years later. 

OCT. 21, 2011

Friends of Guild Park and Gardens

201 Guildwood Pkwy.

Drake released his music video for “Headlines” in 2011, the second single from his album Take Care. The video, which now has more than 200 million views, features a number of Toronto locations, including the CN Tower, the Rogers Centre and Friends of Guild Park and Gardens. “Headlines” peaked on the Billboard charts at No. 6.


Dixon Hall

402 Shuter St.

At the 2010 Juno Awards, Drake was awarded the Allan Slaight Award, a $10,000 honorarium. In order to give back to the city, Drake donated the money to Dixon Hall, a charity that helps provide opportunities for people living in low-income neighbourhoods in Toronto.

NOV. 15, 2011


202 Davenport Rd.

Drake dropped his sophomore album, Take Care, on this day. The record, which received glowing reviews from Rolling Stone, Pitchfork, Spin and more, scored Drake his first Grammy Award for best rap album. The album’s famous cover featuring a solemn Drake sitting alone at a table, holding a chalice, was shot at Joso’s, a restaurant that he frequents. In 2013, Drake shouted out the restaurant in his song “5AM in Toronto.”

NOV. 15, 2011

OVO Flagship Toronto

899 Dundas St. W.

After a few successful pop-ups, OVO opened up its first flagship clothing shop in Toronto’s Trinity Bellwoods neighbourhood. The store featured exclusive merch, some branded with Drake’s new name for the city: the 6ix.


Warner Music Canada

155 Gordon Baker Rd.

Drake, El-Khatib and 40 officially formed OVO Sound in 2012, a label that operates as a subsidiary of, and distributes records through, Warner Records. Upon OVO Sound’s launch, Drake and 40 signed Boi-1da, T-Minus and Mike Zombie as in-house producers. The first artist to sign to OVO Sound was Mississauga native PartyNextDoor.

OCT. 18, 2012

Vaughan Road Academy

529 Vaughan Rd.

When Drake dropped out of Vaughan Road Academy to pursue acting on Degrassi: The Next Generation, he was one credit short from graduating. In 2012, he decided to finish school and earn his diploma. Thanks to a teacher named Kim Janzen, whom he shouted out on Twitter, Drake posted that he had scored 97 per cent on his final exam. “As of tonight I have graduated high school!” he exclaimed online.

15 Fort York Blvd.

Apartment 1503: some couches and paintings/ when you record with two others that want the same things/ it starts to feel better than home feels.

The Ride / Take Care

Photo: Christopher Polk / Getty Images

Pearson International Airport, Terminal 1

I haven’t been inside Terminal 1 and 3 in so long/ I’m driving up to it right now, make sure you got your coat on/ that runway can be cold especially after summer’s rolled on.

The Ride / Take Care

Photo: Christopher Polk / Getty Images

The Weeknd


The Weeknd is one of the biggest pop stars in the world, and the twin pillar to Drake in Canadian urban music. In 2010, Abel Tesfaye, a.k.a. the Weeknd, exploded onto the scene in Toronto, with Drake lending a hand by posting some early singles from the musician’s debut mixtape House of Balloons on his OctobersVeryOwn blog. This put the Weeknd squarely on the music world’s radar, and he quickly sold out his first concert at Toronto’s Mod Club Theatre.

The Weeknd ultimately launched an imprint of his own called XO in 2012, despite rumours that he’d be joining the OVO label. The seeds of their rivalry, whether friendly or not, were likely planted by this choice. The two have continued to collaborate over the years, though, from the Weeknd's contributions to Drake’s highly praised Take Care album to Drake's surprise appearance at the Weeknd's hometown show in 2017. While their paths have diverged significantly since, their work together laid the foundation for Drake’s signature Toronto sound, which now serves as a template for new talent emerging from the city.

Illustration: Line Art Ben Shannon / Montage Andrew McManus

Nothing Was the Same


Drake’s third studio album, Nothing Was the Same, was when audiences really started to see Toronto through the rapper’s eyes. Even though it coincides with his move to Calabasas, Calif., Nothing Was the Same is where Drake provided the city with not one, but two unofficial anthems: “Started from the Bottom” and “Worst Behavior.” The former also comes with a video that is one of the greatest love letters to the city since Kardinal Offishall’s “The Anthem.”

FEB. 13, 2013

Childhood home

9 Coulson Ave.

In early 2013, Drake dropped his music video for “Started From the Bottom,” the first single from Nothing Was the Same. The clip, which now has more than 400 million views, featured locations across Toronto, including his childhood home at 9 Coulson Ave. While some criticized the rapper for describing his Forest Hill origins as the “bottom,” others praised the song and its video, which established some of Drake’s most iconic looks — including shots of him dancing in a Shoppers Drug Mart (located at 3027 Binbrook Rd.) and strutting down snowy Toronto streets next to his car. “Started From the Bottom” was eventually ranked one of the best songs of the year by Rolling Stone, Complex and XXL.

AUG. 2, 2013

Toronto City Hall

100 Queen St. W.

Drake and 40 partnered with the City of Toronto to help form the Toronto music advisory committee. In a post on then-mayor Rob Ford’s Facebook page, it was explained that “the purpose of the advisory committee is to assist with the creation of a strategic action plan that maximizes the impact of city support for the Toronto music industry.” Oliver El-Khatib added: “We’re proud to help the city we love foster music talent and to promote Toronto as a premier music destination.”

SEPT. 19, 2013

OVO pop-up

1000 Queen St. W.

To hype up the release of his new album, Nothing Was the Same, Drake launched three pop-up shops across North America. One of the locations was in Toronto, where fans lined up for hours to get their hands on Nothing Was the Same-themed gear, “compliments of the company.” Those who showed up were rewarded with free black hoodies that featured the album’s title on it in white block font. Drake’s third studio album debuted at No. 1 on the U.S. Billboard 200 and claimed the second highest first-week sales of any album in 2013.

SEPT. 30, 2013

Scotiabank Arena

40 Bay St.

The Toronto Raptors named Drake the team’s global ambassador. At a news conference held at the team’s home, then named the Air Canada Centre, Drake joined Raptors general manager Masai Ujiri, Maple Leaf Sports and Entertainment CEO Tim Leiwekea and then-mayor Rob Ford to announce his new role in leading the team’s rebranding efforts. “I want to bring the excitement into this building, I want a team that people are dying to come see, I want the tickets to be extremely hard to get,” Drake told reporters. “I want to bring that aggression, I want to bring that energy. Obviously, I want it to be a top team in the NBA, if not the top team.”

JAN. 11, 2014

Scotiabank Arena

40 Bay St.

Mere months after he was named the Global Ambassador of the Toronto Raptors, Drake introduced the first-ever Drake Night at Scotiabank Arena. Some people were admittedly confused as to what the special evening entailed other than Drake introducing the players and commentating throughout the game. But, it also marked the beginning of a rumoured rebrand of the team, which included new OVO-themed black and gold colours. (The Raptors did eventually transition to those colours, and future Drake Nights featured limited-edition merch. One item, an OVO-Raptors-branded lint roller, became a much sought-after piece of memorabilia after Drake went viral using one courtside at a previous game. Some were listed for $55,000 on eBay.)

Swish by Han, Ristorante Sotto Sotto and Joso’s

Eatin’ like I’m seated at Swish, Sotto and Joso’s.

5AM in Toronto

Photo: Rick Diamond / Getty Images


Spendin’ all my days on the east side, oh/ forgettin’ who I was on the other side, oh.

Days in the East

Photo: Rick Diamond / Getty Images

Glengrove Avenue

This for shorty up on Glengrove who love when I catch my tempo.

Tuscan Leather / Nothing Was the Same

Photo: Rick Diamond / Getty Images


This ain’t the son you raised who used to take the Acura/ 5 a.m. then go and shoot Degrassi up on Morningside.

Worst Behavior / Nothing Was the Same

Photo: Rick Diamond / Getty Images

Rogers Centre

There’s three balls and a strike. Here’s the pitch. It’s belted deep to centre, Revere goes back, jumps the wall, and it’s gone!

Connect / Nothing Was the Same

Photo: Rick Diamond / Getty Images

Markham Road

I take Eglinton to 401 East and exit at Markham Road in the east end/ where all the pretty girls are sleeping.

Connect / Nothing Was the Same

Photo: Rick Diamond / Getty Images

Budweiser Stage

This has been years in the making/ it’s all for the city, they know I come right every summer.

The Language / Nothing Was the Same

Photo: Rick Diamond / Getty Images

Ristorante Sotto Sotto and Il Mulino

After hours of Il Mulino or Sotto Sotto, just talkin’ women and vino.

Pound Cake/Paris Morton Music 2 / Nothing Was the Same

Photo: Rick Diamond / Getty Images


On the east side of the city, that’s where everybody stay.

The Motion / Nothing Was the Same

Photo: Rick Diamond / Getty Images

Director X


If the image of Drake awkwardly dancing in a turtleneck in front of neon lights is forever burned into your memory, you can thank Director X. Toronto’s Julien Lutz, a.k.a. Director X, is the visionary behind some of Drake’s most memorable videos including Started from the Bottom,” “Worst Behavior,” “HYFR” and “Hotline Bling.” X got his start interning for famed music video director Hype Williams in the late ’90s, working on some of Williams’s most iconic productions, including the 1998 feature film Belly. That was the same year X got his first break as a solo director on EPMD’s “Richter Scale.” From there, X has gone on to direct not only music videos with the likes of Jay-Z, Justin Bieber and, of course, Drake, but also feature films, including the 2018 blaxploitation reboot Superfly. X also introduced Drake to another key music video collaborator, Toronto’s Karena Evans, the young talent behind Drake’s viral videos for songs like “God’s Plan,” “Nice for What” and the Degrassi reunion in I’m Upset.”

Illustration: Line Art Ben Shannon / Montage Andrew McManus

If You're Reading This It's Too Late


More than any other year, 2015 saw Drake at his most prolific. Not only did he release two albums, but he also handily beat Meek Mill in a rap beef while simultaneously paying homage to the Blue Jays’ ’92, ’93 repeat championships. On top of all this, it’s the year Drake truly immortalized Toronto as the 6ix with songs like Know Yourself,” which saw him running through the city with his woes while replacing the longstanding nickname of the T-dot for a new generation of music fans. 

JULY 29, 2015

The SkyDome (formerly)

1 Blue Jays Way

In the midst of a growing feud with Philadelphia rapper Meek Mill, Drake released his second diss track, “Back to Back Freestyle.” The cover art for the single drew just as much attention as the track itself: a photo of Toronto Blue Jays player Joe Carter famously hitting a walk-off home run in Game 6 of the 1993 World Series against the Philadelphia Phillies. In response, Carter joked to TMZ: “Can’t we all just get along?” A few days later, at OVO Fest 2015, Drake opened his show with his diss tracks, “Charged Up” and “Back to Back Freestyle,” while memes of Meek Mill were projected behind him.

Kennedy Road

I got real ones livin’ past Kennedy Road/ I got real ones with me everywhere that I go.

Energy / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images

15 Fort York Blvd.

Yeah, this that Oliver, 40, Niko shit man/ 15 Fort York shit, y’know?

Know Yourself / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images


Now I’m in the east ’cause my boys are gettin’ right.

Star67 / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images


Sauga city trip the payday.

Preach / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images

The Hazelton Hotel

I’ll tell ‘em link up at the valet at the Hazy.

Used To / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images

Weston Road and Scarlett Road

Do you remember back to Weston Road, Scarlett Road?

You and the 6 / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images

Lawrence Heights

She from the jungle, she from the jungle.

Jungle / If You’re Reading This It’s Too Late

Photo: Kevin Winter / Getty Images

What a Time to Be Alive


At the height of his power in 2015, Drake released a second mixtape, What a Time to Be Alive, his collaboration with Atlanta rapper Future. Featuring continued digs at Meek Mill, the tracks acted as a victory lap for Drake while broadening his list of close collaborators (producer Metro Boomin takes the reins on the majority of the production along with 40, Boi-1da and Frank Dukes in supporting roles). The album became both Drake’s and Future’s second to debut at No. 1 on the Billboard 200 that year, solidifying both artists’ firm grip on the charts.


Ryerson University

350 Victoria St.

Drake made Ryerson’s downtown campus the place to be by making a surprise appearance at the university’s frosh week events with special guest Future in 2015. If that wasn’t enough, he did it again the following year.

SEPT. 21, 2015

Fring’s (now closed)

455 King St. W.

Drake celebrated the opening of Toronto chef Susur Lee’s new restaurant, Fring’s shortly after his Ryerson appearance. While many assumed he was connected to the business — his own business partner, Angelo Ferraro, co-owned the joint with Lee’s family — Drake’s biggest role was providing the restaurant with its name. In a statement to the New York Times, Drake explained that the phrase meant “something you pull from your own emotions, from a happy time.” Fring’s closed on June 23, 2018.

SEPT. 30, 2015

The Bridle Path

North York, Toronto

In 2015, Drake bought $6.7 million worth of property in Toronto’s Bridle Path neighbourhood to construct his own home, which is estimated to be a 40,000 square-foot mansion. Four years later, the project is still in progress but fans have gotten glimpses of the space including an OVO-branded indoor basketball court.

NOV. 19, 2015

Toronto’s most influential


Monthly magazine Toronto Life named Drake the No. 1 most influential person in the city. He beat out political figures John Tory and Kathleen Wynne, as well as the former Toronto Blue Jay José Bautista, Bell Media’s Randy Lennox and fellow musician the Weeknd. “Today, as far as the rest of the world is concerned, Drake is Toronto,” the publication stated.

Scotiabank Arena

I got a club in the Raptors arena/ championships, celebrations during regular seasons.

30 for 30 Freestyle / What a Time to Be Alive

Photo: Kevin Winter / Getty Images



There are two ways to look at Drake precariously perched atop the CN Tower on the album cover of Views: He could be the lonely megastar, whose immense fame only makes him more reclusive, preferring the solitary height of the tower to the rest of the world, or he could be the triumphant king, perched atop the city’s most iconic structure, looking down at what he’s helped create. But on the album itself, Drake was both. Views was where we got some of Drake’s most self-reflective lines, but we also got some of the best odes to his hometown. 

FEB. 22, 2016

The Real Jerk

842 Gerrard St. E.

In January 2016, Rihanna dropped her single Work,” featuring Drake. The track became his third No. 1 Billboard Hot 100 single, and his second with Rihanna after 2010’s What’s My Name.” The video, which Rihanna released the following month, was shot by Director X at Toronto’s the Real Jerk restaurant. While the restaurant’s co-owner, Edward Pottinger, was hesitant to rent out the space at first, he later on agreed, telling CBC Toronto: “I realized how powerful it would be to have the name associated with us. Realizing it was the No. 1 male and female rapper/pop stars in the world, it was, ‘OK, let’s do this thing.’”

APRIL 24, 2016

CN Tower

301 Front St. W.

You can’t be the king of the 6ix without the hardware to match, so it’s appropriate that Toronto Mayor John Tory gave Drake the key to the city on this day. Prior to this, Drake and the mayor met for a closed-door, 90-minute meeting in which the rapper expressed his concerns for the city, including his thoughts on gun violence and the need for more programs for at-risk youth.

JUNE 19, 2016

Drake’s tourism appeal


The Toronto Star reported that Drake’s influence and impact on Toronto’s economy, either through tourism or branding by using the name “the 6ix,” was worth “in conservative terms, at least $3 million,” according to research firm Charlton Strategic Research Inc. Another firm, Enigma Research, estimated that Drake’s annual OVO Fest drew in “$5 million on the low end and up to $20 million” in business for places like hotels, restaurants and the tourism industry in general. Two years later, Vice wrote a similar piece, claiming that the rapper could be responsible for five per cent of Toronto’s $8.8-billion US tourism economy. While it's difficult to quantify the exact cost of Drake's impact, it's undeniable that his fame has increased the city's tourism appeal.

JULY 31, 2016

Ripley’s Aquarium of Canada

288 Bremner Blvd.

Rihanna made her first surprise appearance at OVO Fest in 2016, performing her Drake collaborations Work” and “Too Good,” as well as “Needed Me” and “Bitch Better Have My Money” off of her album Anti. The night before this performance, Drake and Rihanna allegedly went on a late-night date at Ripley’s Aquarium of Canada. “He booked out the place after midnight and had them set up a fancy dinner right in front of the glass,” LaineyGossip reported. In September, Rihanna showed off a new camouflage shark tattoo that many suspect is a replica of a toy shark Drake gave her on this date

SEPT. 30, 2016

Virginia Black

Various locations

In 2016, Drake announced his latest business venture: liquor. Virginia Black was his new brand of whisky, which collaborator and beverage entrepreneur Brent Hocking described as “uniquely positioned to redefine American whisky.” While it’s unclear if it fully redefined anything, it was a smash hit in Ontario when it hit shelves in September. On its first day at the LCBO, it broke the record for the largest single-day launch sales in the store’s history. A few weeks later, Virginia Black became available in B.C., Manitoba and Alberta. 

Four Seasons Hotel

Out front of Four Seasons lookin’ like a damn football team.

Summer Sixteen

Photo: Kevin Winter / Getty Images

Kennedy Road

Kennedy Road taught me not to trust people like you.

Keep the Family Close / Views

Photo: Kevin Winter / Getty Images


You was ridin’ TTC metro, I had the place boomin’.

Weston Road Flows / Views

Photo: Kevin Winter / Getty Images

Fluid Lounge (now closed)

Big Apple had the white Hummer parked right in front of Fluid.

Weston Road Flows / Views

Photo: Kevin Winter / Getty Images

Jane Street and Weston Road

How did I finesse all of this shit from Jane and Weston?

Still Here / Views

Photo: Kevin Winter / Getty Images

4301 Kingston Rd.

This sound like some 43-01 shit.

Pop Style / Views

Photo: Kevin Winter / Getty Images

Jaydees Connections

I worked at Jaydees Connections whenever Jason let me.

Views / Views

Photo: Kevin Winter / Getty Images

Ceesay’s M&M Sporting Goods

Ceesay’s I was buyin’ fitteds everyday.

Views / Views

Photo: Kevin Winter / Getty Images

Dufferin St. and Eglinton Ave. W.

Kiddie Caribana, tryin’ not to catch a stray.

Views / Views

Photo: Kevin Winter / Getty Images

The Bridle Path

Architects takin’ dimensions, they redoin’ the entrance.

4PM in Calabasas

Photo: Kevin Winter / Getty Images

More Life


Even when Drake has global ambitions — such as on the genre-spanning playlist More Life, which covers everything from London grime music to Afrobeats and South African house — he still has Toronto in the back of his mind.

SEPT. 9, 2017

The Princess of Wales Theatre

300 King St. W.

At the 2017 Toronto International Film Festival, Drake attended the screening of The Carter Effect, a documentary about the career of former Raptors player Vince Carter. In addition to starring in the film, Drake was also credited as a producer alongside Future the Prince, LeBron James and Maverick Carter. In 2018, The Carter Effect was picked up by Netflix.

Vaughan Road Academy

Vaughan Road Academy, star player.

Two Birds, One Stone

Photo: Kevin Winter / Getty Images


It’s a east side ting, eh?

Free Smoke / More Life

Photo: Kevin Winter / Getty Images


If Gilla call shots, no questions/ G-Way ’til I’m resting/ but we still got love for the west end.

No Long Talk / More Life

Photo: Kevin Winter / Getty Images


Can’t get Nobu, but you can get Milestone.

Gyalchester / More Life

Photo: Kevin Winter / Getty Images

The Bridle Path

I gotta do mansion ’cause I outgrew condo.

Gyalchester / More Life

Photo: Kevin Winter / Getty Images


It’s a Habibiz ting.

Portland / More Life

Photo: Kevin Winter / Getty Images

Queen Street

Queen Street visions that nobody believed in.

Lose You / More Life

Photo: Kevin Winter / Getty Images

Niagara Falls

We evolved, used to think vacation meant Niagara Falls.

Can’t Have Everything / More Life

Photo: Kevin Winter / Getty Images


All that Drake hysteria/ 6 side, east side, all that for my area.

Can’t Have Everything / More Life

Photo: Kevin Winter / Getty Images

SilverCity Cinemas and Indigo Books

Yeah, used to be at SilverCity, Indigo.

Do Not Disturb / More Life

Photo: Kevin Winter / Getty Images

Rogers Centre, formerly known as Skydome

Might move our annual shit to the ’Dome/ I need 40,000 people to see what I’m on.

Do Not Disturb / More Life

Photo: Kevin Winter / Getty Images

Club Palazzo

Went from Club Palazzo in the Bridge to Club LIV.

Do Not Disturb / More Life

Photo: Kevin Winter / Getty Images



By 2018, Drake had broken so many sales records that he became bigger than the Beatles. An unprecedented seven songs from Scorpion landed within the Billboard Top 10 simultaneously, topping the Beatles' 1964 record of five. Scorpion also became the first album to be streamed one billion times in its first week, which was helped by the strength of No. 1 songs “God’s Plan,” “Nice for What” and “In My Feelings.” Pair that with a historic championship win by the Toronto Raptors, and it put Drake — and his city — on top of the world. 

MARCH 14, 2019

Toronto Raptors Training Centre

30 British Columbia Rd.

As part of a new naming rights deal, the Toronto Raptors renamed their training facilities the OVO Athletic Centre. Drake, who’s been the basketball team’s global ambassador for six years, took to social media to share the news: “I am so proud of my brothers and so proud to be from this city,” he wrote. “I swear this one feels like a high school dream and it’s a blessing to be able to raise up the levels and make the human mind stretch when it comes to thinking about what is possible in your lifetime!” The outside of the building was also rebranded with a gold Raptors basketball logo next to OVO’s owl symbol. 

JUNE 13, 2019

Raptors Championship

Scotiabank Arena, 40 Bay St.

After a tense NBA playoffs run, which included Drake getting criticized for his wild courtside behaviour and trading barbs with Golden State players Kevin Durant and Steph Curry, the Raptors won their first NBA championship title in June 2019. While the winning game took place at Oakland’s Oracle Arena, Drake watched on with hundreds of fans outside Scotiabank Arena at Jurassic Park. When asked by the press how the win felt for him, he said, “This is poetic. The 6ix in six.” Two days later, he released two new songs, “Omertà” and “Money in the Grave” featuring Rick Ross, to celebrate the momentous win.

AUG. 1-2, 2019

TIFF Bell Lightbox

350 King St. W.

Cryptic OVO X RBC co-branded billboards began appearing across Toronto, but were soon revealed to be teasers for a new edition of the OVO Summit, an “immersive conference for Canadian creatives and lifestyle entrepreneurs” that’s part of Drake’s annual OVO Fest. This marked the first time OVO Summit would be open to the public and it specifically targeted young people looking to grow their careers and “make a lasting impact on the creative economy in Canada.” 

AUG. 3, 2019

OVO Store Eaton Centre

CF Toronto Eaton Centre, 220 Yonge St.

To coincide with OVO Fest, OVO opened its fourth Toronto storefront in one of North America’s busiest shopping malls, the Toronto Eaton Centre. The 2,890 square-foot space was formerly occupied by Lululemon and features interior columns imported from Portugal as well as steel fixtures and marble stone plinths brought in from Italy. On the morning of its opening, a line of fans snaked around the mall’s third floor waiting to purchase the latest OVO merch. 

AUG. 4-5, 2019

9th Annual OVO Fest

Budweiser Stage, 909 Lake Shore Blvd. W.

After taking a year off, OVO Fest returned in 2019. The two-day concert included performances by B2K, Mario, Pretty Ricky, Lloyd, Ying Yang Twins, Chingy and Bobby V on the first night, with Drake headlining the second. Drake’s evening featured a giant replica of the Larry O’Brien trophy as well as the real one, which the rapper walked onstage holding. As usual, Drake also invited a number of high-profile guests to perform: Cardi B, Chris Brown, Rick Ross, Meek Mill, Tyga, Da Baby, Megan Thee Stallion and Gucci Mane.

The Bridle Path

All factual, I call the house ‘the embassy’/ the studio ‘the chapel,’ I hate to travel.

Diplomatic Immunity / Scary Hours

Photo: Frazer Harrison / Getty Images


Vegas like Marineland, that big whale treatment.

Elevate / Scorpion

Photo: Frazer Harrison / Getty Images

Weston Road

I finessed down Weston Road, ayy, ’nessed.

God’s Plan / Scorpion

Photo: Frazer Harrison / Getty Images

Scarlett Road

I’ve been me since Scarlett Road, ayy, road, ayy.

God’s Plan / Scorpion

Photo: Frazer Harrison / Getty Images

The Ritz-Carlton

Sick of this shit, move to the Ritz.

Mob Ties / Scorpion

Photo: Frazer Harrison / Getty Images



Watch the eight-part series Drake’s Plan on CBC Gem.

CBC Listen

Drake & Co.

Listen to the Drake & Co. playlist on CBC Listen.

CBC Music

Explore a Decade of Drake on CBC Music.

Animation of Drake dancing

Drake’s Toronto


Produced by Jesse Kinos-Goodin & Melody Lau
Researched & Written by Caitlin Dosa, Jesse Kinos-Goodin, Melody Lau & Ian Steaman
Copy Edited by Sheena Goodyear, Holly Gordon & Lakshine Sathiyanathan

Designed by Andrew McManus
Developed by Mike Evans, Geoff Isaac & Rebecca Viegas
Animation & Line Art by Ben Shannon

Executive Producers
Ben Aylsworth & Paul Gorbould

Senior Producers
Jess Huddleston, Chantale Maynard & Andrew McManus

Special Thanks
Chelsey Gould

©2019 CBC/Radio-Canada. All rights reserved.