WEATHER ALERT

Leave it to Chance

Chicago rapper celebrates 10th anniversary of groundbreaking mixtape

Advertisement

Advertise with us

Chance the Rapper made history in 2016 with the release of his third mixtape, Coloring Book.

Read this article for free:

or

Already have an account? Log in here »

To continue reading, please subscribe:

Subscribe and receive a limited-edition Free Press branded hat or tote.

Digital Subscription

One year of digital access for only $205*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*First annual payment billed as $205.00 + GST for one year. This annual subscription will automatically renew at $233.00 + GST every 52 weeks (10% off the regular annual price of $259.35). Offer available to new and qualified returning subscribers only. Cancel any time.

To continue reading, please subscribe:

Add Free Press access to your Brandon Sun subscription for only an additional

$1 for the first 4 weeks*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles
Start now

*Your next Brandon Sun subscription payment will increase by $1.00 and you will be charged $17.95 plus GST for four weeks. After four weeks, your payment will increase to $24.95 plus GST every four weeks.

Chance the Rapper made history in 2016 with the release of his third mixtape, Coloring Book.

The Chicago-born hip-hop artist released the album independently and exclusively through Apple Music, making it the first streaming-only album to earn a Grammy when Chance won Best Rap Album at the 2017 music awards.

The mixtape — which blends gospel with rap and features collaborations with Kanye West, Lil Wayne, Young Thug and others — also received wide critical acclaim.

SUPPLIED
                                Chance the Rapper plays the Canada Life Centre July 13 with Big Boi.

SUPPLIED

Chance the Rapper plays the Canada Life Centre July 13 with Big Boi.

Chance, 33, is touring North America this summer to celebrate the 10th anniversary of Coloring Book, including a stop at Canada Life Centre on Monday. Audiences can expect hits from that seminal project, along with music from his latest release, Star Line.

Rapper and producer Big Boi of Outkast fame supports.

The Free Press caught up with Chance over a video call from his hometown ahead of his Winnipeg appearance.

Free Press: Not every artist revisits their past releases in such a major way. Why is that important to you?

Chance the Rapper: I guess I’m just really proud of my work. And music that I like is music that I’ve examined over time and learned more and more from and experienced in different ways. Like the Miseducation of Lauryn Hill — I’ve been listening to that since I was a kid and I still learn new things from it. College Dropout (by Kanye West), same thing.

Good art grows with you and you have different perspectives on it over time. And so I think I always look at my art in a proud way. I’m kind of distant from it when it first comes out because there’s a separation anxiety I get when I’m not able to work on it as a fluid, growing thing anymore. But then I get to go on tour and love it all over again.

The best thing about doing anniversary shows … is that I’m just older and better at performing and arranging sets. So I’m really excited for this one because Coloring Book changed my life.

FP: Are there any songs on that album that have changed for you over the past decade, in terms of meaning or importance?

CTR: I really, really love doing Summer Friends. Even if some of the lyrics are already nostalgic, that’s how I felt about things at 23. I’m talking about childhood and I’m talking about relationships from my childhood. But then there’s other songs that are dissonant because my life has changed so greatly.

One of the coolest things that (comedian) Dave Chappelle told me when I was much younger is that albums are like yearbook photos. They’re not a portrait of your life, they’re a snapshot, true documentation of who you are in a moment.

FP: How do you think the music industry has changed, positively or negatively, for independent artists since the release of Coloring Book?

CTR: It’s become more of a viable option. Some of the biggest artists in the world are independent — Brent Faiyaz, Clairo. There’s definitely more investment from fans in making sure that the artists they listen to are happy and successful, and even happy in their contracts.

As a whole, the industry isn’t designed for artists to be in ownership positions or directing the profits. I think Coloring Book definitely laid the groundwork for there to be more conversations and I hope streaming gets to a place of equity for artists.

FP: You’ve been touring a lot recently in support of Star Line and you’re heading out again this summer for the Coloring Book anniversary. How has your approach to touring changed over the years?

SUPPLIED
                                Chance the Rapper says he’s now making a point to take in the culture of the cities he performs in.

SUPPLIED

Chance the Rapper says he’s now making a point to take in the culture of the cities he performs in.

CTR: I genuinely love touring. I’ve been touring since I was 18. When I was younger I didn’t do nothing in the cities. I would sit on the bus, maybe go out to a club after my show, but I wasn’t really going to museums or meeting real people. Now, I’m getting to the point where I respect the opportunity to learn about the culture of different cities. I also love getting to see people that love the art that I made.

FP: What do you like to bring on the road to make the travel more comfortable or enjoyable?

CTR: I have a portable PS5 case that has a screen in it, that’s pretty lit. I used to play the Fight Night games … and this new one came out called Undisputed, and it has all the fighters and my favourite game mechanics. It’s just a great boxing game (Chance is a major boxing fan).

And I’ll bring some literature and portable chargers.

FP: What are you reading right now?

CTR: I’m reading two books right now, The Wretched of the Earth by Frantz Fanon and Parable of the Sower by Octavia E. Butler, which is like a prophetic fictional account of this president that’s taking over the world. I’ve never read fiction my entire life, I mean (aside from) when we were in grammar school, but I’m getting into it.

FP: You recently played a Juneteenth show at the Hollywood Bowl and described it as one of your favourite performances. What was so important about that show, especially within the context of the 250th anniversary of the United States?

CTR: We’ve got dirt bikes and wrestling matches at the White House right now. There’s not really any sort of concentrated effort to right the wrongs of the past and it’s actually becoming a celebrated thing to destroy history in my country. I have the opportunity to be a writer, a journalist, a documentarian of life and to give context to the songs that I’m performing. The night went off without a hitch; it was beautiful and peaceful.

This interview has been edited for length and clarity.

eva.wasney@winnipegfreepress.com

Eva Wasney

Eva Wasney
Reporter

Eva Wasney has been a reporter with the Free Press Arts & Life department since 2019. Read more about Eva.

Every piece of reporting Eva produces is reviewed by an editing team before it is posted online or published in print — part of the Free Press‘s tradition, since 1872, of producing reliable independent journalism. Read more about Free Press’s history and mandate, and learn how our newsroom operates.

Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

Report Error Submit a Tip

More Stories

Bombers backup Brown takes the reins in clash against Argos

Ken Wiebe 7 minute read Preview

Bombers backup Brown takes the reins in clash against Argos

Ken Wiebe 7 minute read Thursday, Jul. 9, 2026

Mike O’Shea isn’t a big fan of letting reporters under the hood when it comes to how certain decisions get made.

Yet, as the head coach of the Winnipeg Blue Bombers was pressed for information on how he came to his final conclusion before naming Dru Brown his starting quarterback for Friday’s showdown with the Toronto Argonauts, O’Shea worked through a number of questions before revealing this decision eventually made itself.

“We brought Dru in for a reason. We brought Dru in for this reason,” said O’Shea, noting the final call wasn’t made until Thursday morning. “So, you execute the plan as it was laid out.”

Asked a follow-up question for clarification, O’Shea made it clear that he prefers not to deal with hypotheticals, even if precautions are made to cover all of the bases.

Read
Thursday, Jul. 9, 2026

Indigenous theatre founder gets nod for prestigious prize

Ben Waldman 3 minute read Preview

Indigenous theatre founder gets nod for prestigious prize

Ben Waldman 3 minute read 2:02 AM CDT

For her work as the founding artistic director of Oshkagoojin Indigenous Theatre for Youth, Winnipeg’s Nova Courchene has been named the recipient of one of Manitoba theatre’s highest honours for emerging arts leaders.

Since 2023, the Cherry Karpyshin Arts Management Prize has been given out by Prairie Theatre Exchange to early-career or aspiring arts managers. Named for PTE’s longtime general manager, for whom the company’s mainstage is also named, the Cherry Prize is accompanied by professional supports and a $2,500 cash award.

Meaning “new moon” in Anishinaabemowin, Oshkagoojin runs a variety of initiatives in Winnipeg, including the teen-focused Rising Voices, the middle years Growing Voices, and the early years Young Voices programs. Through storytelling, movement, narrative games and guided play, the Young Voices program introduces Indigenous children aged five through nine to the fundamentals of collaborative and co-operative theatre with a curriculum devised through a cultural lens.

“As I continue to grow Oshkagoojin Indigenous Theatre for Youth, I look forward to strengthening the organization’s capacity, sustainability, and national reach so that more Indigenous young people can access theatre, cultural learning, and artistic leadership opportunities in their own communities,” says Courchene in a release. “I believe that when Indigenous youth are empowered to tell their stories, entire communities benefit, and I am excited to continue building these pathways for future generations.

Read
2:02 AM CDT

‘Difficult day’ as man pleads guilty to impaired driving in bride-to-be’s death near Portage

Tyler Searle 4 minute read Preview

‘Difficult day’ as man pleads guilty to impaired driving in bride-to-be’s death near Portage

Tyler Searle 4 minute read Thursday, Jul. 9, 2026

PORTAGE LA PRAIRIE — Driving a stolen truck with meth in his system, James Lorne Hilton lost control on a highway near Portage la Prairie last winter and caused a crash that killed a beloved bride-to-be, court heard Thursday.

Hilton, 25, appeared in the Court of King’s Bench and pleaded guilty to impaired driving causing death and failing to remain at the scene of the Jan. 15, 2025, collision that killed 28-year-old Kellie Verwey.

“This is a difficult day,” Crown prosecutor Mike Himmelman said as the proceedings began, addressing more than a dozen of Verwey’s family, friends and supporters who gathered in court to hear Hilton admit to his crimes.

Reading from an agreed statement of facts, Himmelman described how Hilton was driving westbound on Highway 26 on the morning of the collision when he veered into the opposing lane and caused another pickup truck to lose control.

Read
Thursday, Jul. 9, 2026

Westman residents fear power project’s wind turbines will sully their idyllic landscape

Julia-Simone Rutgers 16 minute read Preview

Westman residents fear power project’s wind turbines will sully their idyllic landscape

Julia-Simone Rutgers 16 minute read Yesterday at 7:00 AM CDT

POLONIA — Leonard Kaspick can list just about every household in the valley.

“There’s someone living right across the northeast, someone living behind here, about a quarter mile there’s a house there, then a half mile there’s another house there, I’m here, and then on top of the hill there’s someone else there,” he says, standing in the heart of the hamlet — a community hall just off the main drag.

Besides the hall and the smattering of homes, there’s a historic (though out-of-commission) church next door and a single general store further down the road.

“There’s less people here now than there was in 1885,” Kaspick, 83, jokes as he wraps up a condensed history of the western-Manitoba community.

Read
Yesterday at 7:00 AM CDT

Apartment rents continue to climb in Manitoba

Free Press staff 2 minute read Preview

Apartment rents continue to climb in Manitoba

Free Press staff 2 minute read Yesterday at 2:01 AM CDT

Winnipeg saw a marginal increase — 0.9 per cent — to $1,678, according to a July 2026 Rentals.ca report, which shows June data.

Read
Yesterday at 2:01 AM CDT

Uncertainty bakes costs into CUSMA chain

Laura Rance-Unger 5 minute read Preview

Uncertainty bakes costs into CUSMA chain

Laura Rance-Unger 5 minute read 2:02 AM CDT

Despite all the melodramatic hype and handwringing leading up to it, the July 1 timeline for renewing the Canada-United States-Mexico Agreement on trade passed without a U.S. commitment to extend its 2036 sunset.

The sun still rose the next day. Trucks and trains are still crossing the border carrying Canadian commodities (albeit not on that new bridge named after a famous hockey player). Grocery stores still carry imported fruits and vegetables from the south, and Canadians in several provinces still can’t buy American liquor.

Nothing changed, except everything.

We must now accept the certainty of continued uncertainty as Canada, along with the rest of the world, considers how to deal with the increasingly erratic leadership at the helm of the world’s largest economy.

Read
2:02 AM CDT